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Outbound Squad

5 Oct 2026 · 1h 18m · 33 chapters

Episode artwork

Future of Saas, moats, pipegen, and more with Ryan Heaphy

In short

Early-stage SaaS go-to-market: why most SaaS startups fail early, what “the playbook” must include before hiring, how to build founder-led sales into a repeatable sales motion, and how to hire/coach the first reps and leaders.

Guest backgrounds

Ryan Heaphy is Head of Sales Strategy (advisor/operating partner) at Fractal Software, advising 150+ vertical SaaS startups across seed to Series A. He previously worked in sales leadership roles (rep through VP) and joined Qualia when it was ~30 employees, becoming top seller and shaping early sales processes. He started in hospitality at the Ritz-Carlton in the Virgin Islands, where he interacted with President’s Club winners and later moved to Austin to begin sales.

Key claims

SaaS “make or break” is 0–$1M to $1–$10M; failure odds drop after ~$10M. VP-of-sales is often wrong too early; the right early hire is typically a director-level leader who stays hands-on. “Player-coach” can hurt performance unless expectations are clear. Seniority/time isn’t the same as skill; hiring should target 1–5 years full-cycle experience. Mock cold calls are the best hiring test; coachability is critical.

Notable examples

Qualia—joined pre-scale, closed 60+ platform deals in year one, coached peers by demoing and staying late. Hiring cohorts: founders shouldn’t expect everyone to hit quota; use 2+ hires for an A/B benchmark. Mock cold call: candidate must pitch what they sell day-to-day; objections include “send me an email,” “not the right person,” and “we’re set.”

Written by AI. May contain mistakes.

Chapters

0:00

The High Stakes of SaaS Startups

Learn about the significant failure rates of SaaS startups and critical growth stages.

“92 % of SaaS startups fail within their first three years.”
1:10

Trends in Sales and Market Challenges

Discuss the current trends in sales strategies, including challenges faced in lead generation.

“about helping you turn complete strangers into paying customers.”
4:03

Reconnecting with Ryan Heaphy

The hosts reconnect with Ryan, discussing changes since his last appearance.

“Dude, I want to say that were we introduced through Scott?”
4:23

Ryan's Unique Career Journey

Explore Ryan's diverse career path from the Ritz-Carlton to sales leadership.

“New job, new kid, new house, new car, new everything, man.”
5:15

Transitioning into Sales

Ryan shares how he transitioned from hospitality to a career in sales.

“Well, I'm excited to jam with you because you've had such a unique career in the sense that like you've done the IC rules.”
7:08

Navigating the Job Market in Austin

Ryan details his move to Austin and the challenges he faced finding his first sales job.

“But on the days I had off, man, I was living in paradise and it was nice.”
8:13

The Path to Sales Leadership

Discussing Ryan's motivations and path towards a leadership role in sales.

“What was like the spark where you're like, okay, cool.”
8:45

Success and Challenges in Leadership

Ryan reflects on his leadership journey and the dynamics of leading sales teams.

“I don't know that there were many dots connected there.”
10:40

Advising SaaS Companies

Learn about Ryan's current role advising SaaS companies and the strategies he employs.

“And it was the weekend before I was supposed to start on Monday.”
14:00

Ryan Heaphy's Journey in Sales Leadership

Learn how Ryan Heaphy transitioned from a top sales rep to a sales leader, emphasizing the importance of proactive leadership.

“So how do you end up doing what you're doing now, like really advising a lot of the companies?”
Show all 33 chapters
16:21

Challenges of the Player-Coach Model

Explore the downsides of the player-coach model and the impact on sales performance.

“Like even with the best intentions, if you give somebody who wants to be a leader and say, hey, yeah, do all this extra responsibility, they want to do that.”
19:29

Creating a Culture of Leadership in Sales

Discover how to foster a culture where sales reps take initiative and lead without formal titles.

“Yeah, I think of it again as sort of the same way because I've asked I've been asked this question every day and I'm sure I will continue to be because people want to aspire to leadership.”
22:21

Founder's Role in Building Sales Frameworks

Understand the importance of founders in establishing foundational sales processes and delegating effectively.

“So I think like a blanket statement that I'll always just put out there is you have to just lead.”
24:57

Scaling Sales Teams: The Right Approach

Learn Ryan's insights on when and how to build a sales team, including hiring strategies and roles.

“So in terms of like, can you walk us through actually, because I think this will give some context into this and some of the other things that we're going to talk about.”
28:00

Common Hiring Pitfalls for Founders

Learn about common mistakes founders make when hiring sales roles.

“Everything else spans a spectrum of everything you just mentioned.”
29:16

Defining a Sales Playbook

Understand the essential components of a sales playbook for startups.

“The other one that you mentioned is, okay, I have a dozen customers.”
30:34

The Importance of a Strong Sales Process

Discover why having a structured sales process is critical for success.

“Because it means so many different things to so many people.”
32:52

Hiring the Right Sales Talent

Explore strategies for hiring effective sales talent in startups.

“And And in terms of like the first round of hires, I don't know if you've seen some of the stuff on LinkedIn lately around like the founding AE.”
36:24

Cohort Hiring Strategies

Learn about the benefits of hiring in cohorts and the expected outcomes.

“If you have the capacity and the will to like handhold all those things, great.”
38:41

Testing New Sales Recruits

Find out effective methods to evaluate sales candidates during hiring.

“They seem to be building like, you know, some good pipeline.”
42:00

Hiring Profiles and Testing Fit

Learn about effective hiring profiles and techniques for testing fit in candidates.

“other reps to compete against dudes yeah there you go um yeah let's spend a little bit more time in the hiring profile.”
44:50

Evaluating Coachability in Candidates

Understand how to assess coachability during the hiring process and its importance.

“I just feel like what's a role play, people just give them super easy role plays most of the time and they don't really give them too many objections, you know?”
48:40

Sales Team Growth and Management

Explore strategies for scaling sales teams and determining the right leadership roles.

“When you're in the interview process, you have to do things to show that you're coachable, to show you can grow, to show you can learn.”
53:00

The Importance of Titles in Sales

Discover the implications of job titles in sales organizations and their impact on team dynamics.

“But they haven't cold called in a very long time.”
55:40

Sales Math and Forecasting

Gain insights into setting quotas and understanding the forecasting process in sales.

“It's like, why do they have a CRO and they're hiring their first salesperson?”
56:04

Setting Sales Targets and Forecasting

Explore the complexities of setting individual sales quotas and the importance of accurate forecasting.

“They're given a target or it's been kind of predetermined for you, at least as the sales leader, right?”
58:58

Understanding Pipeline Coverage in Sales

Learn about the significance of pipeline coverage and its impact on achieving sales quotas.

“like, yeah, you might be given your target.”
1:03:11

Cold Calling Strategies for Pipeline Generation

Discuss effective cold calling strategies and the importance of multi-threading in sales outreach.

“So when I asked you this before, you're like, cold calling.”
1:10:01

Evaluating Sales Performance

Learn how to assess the effectiveness of sales calls and identify coaching opportunities.

“Is it number of accounts that we've set meetings through?”
1:13:01

The Use of Parallel Dialers

Discover the advantages and limitations of parallel dialers in sales.

“Um, I guess one thing I'll just note since it comes to mind is like parallel dialers are super in right now.”
1:14:18

Accepting the Sales Reality

Understand the importance of engaging deeply with accounts in sales.

1:14:54

Decompressing After a Tough Week

Explore personal strategies for relaxation and stress relief after work.

1:16:47

Connecting with Ryan Heaphy

Learn how to connect with Ryan Heaphy for insights and collaboration.

“You can find me on LinkedIn, Ryan Heafy.”
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Transcript

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0:0092 % of SaaS startups fail within their first three years. About 48.4 % of those fail within the first five years. So that zero to one million, that one to 10, these are, for anyone listening to this, if you've worked at a company in that stage, you know that these are the kind of make it or break it moments in a company. We either build the momentum that we need and we build it here and create that flywheel or we don't. Typically happens at that stage. Once a company gets to a certain revenue level, especially 10 mil plus, the odds of failure decrease dramatically. In today's episode, what we're going to dig into, we're going to talk to someone who I've gotten to know well in the last couple years, who's been on the show actually and advises 150 plus startups at a company called Fractal Software.

0:53It's pretty cool. He's also been in the seat as a rep, a manager, a director of sales, a VP. He's done the whole gamut. And what we're going to talk about today is really that early stage. What's important to really nail. But before we get to that, my name is Jason. I'm CEO at Outbound Squad. We're all about helping you turn complete strangers into paying customers. The thing that we focus on a lot is pipe gen. So a really big trend that we see right now is that marketing and demand gen has gotten very expensive. Right? Lead volumes down. It's very costly to hire SDRs. The SDR model is not dead, but it is certainly broken in many orgs, especially the ones that we work with.

1:39And we're seeing really big trend around AEs needing to self-source around, hey, we need to move up market because these are bigger logos that we can go after. So the ROI on this effort is going to be much higher. Hey, we need to leverage AI to increase efficiency. All of those things are big themes that come up in the work that we do with clients like Shopify, Zoom, Rippling, iHeartMedia, Amex, and startups building out their first SDR teams as well. So if those are things that you're thinking about that you're working on, you're definitely in the right place. So the conversation today, we're going to be talking to Ryan Hefe, who has been on the show before.

2:19He's at Fractal Software. He advises 150 plus vertical SaaS orgs on their go-to-market motion. So this is like building out their first sales teams, moving away from founder-led sales. This is building out your sales playbook. We got to meet in person when we were in Austin, actually, which was really cool. But he talked about how he got into sales. He used to work at the Ritz-Carlton in the Virgin Islands. And that's how he met a lot of these reps. They were in President's Club. He's going to talk about that a little bit more. He's going to talk about product differentiation and what the true moat in SaaS is with all of the vibe coding and all of that stuff that's going around.

2:59We're going to talk about what's working with PipeGen, all of that really good stuff. So before we get to the episode, if you need help implementing some of the stuff that we talk about on this podcast with your sales team, specifically around outbound PipeGen, So how they build pipeline, how they get referrals, how your managers coach and reinforce this, what your onboarding program looks like for your SDRs, et cetera. Shoot me an email. It's Jason at outbound squad.com. Our promise is that we will help you increase qualified pipeline by 20 % or more within 90 days. We've done that for 250 plus sales teams in the last five or six years.

3:37We'd love to talk to you. And then one other thing that I would give is we have a free masterclass, an outbound masterclass. So if you're wanting to see more about our methodology and how it works and, you know, if our content is for you and all that good stuff, outbound squad.com slash masterclass, that's where you can get access to that. Go grab it. It's free. There's about three hours of some of the best content you're going to find out there on outbound. All right, let's get to the episode with Ryan.

4:09Dude, I want to say that were we introduced through Scott? Scott, at least. Possibly. Or you might have reached out or I can't remember exactly, but you were on the pod five years ago. Five years ago, yeah, 2021. Yeah, life's a lot different now than it was in 2021 for you, huh? Yeah, sure is. You got a new kid, new job. New job, new kid, new house, new car, new everything, man. Did you have hair last time we talked to you? I had hair, yeah. I still have hair, actually. This was somewhat of a choice. I recently tried to trim my hair between cuts and totally screwed it up and just nuked it. And then I'm like, dude, this is nice.

4:50It is really nice because I kind of need to do it because my hair is receded all the way up here. Yeah. But not having to worry about putting product in your hair or wearing a hat if your hair doesn't look good is pretty money, man. It's liberating. My wife keeps saying, you look like The Rock, dude. I'm kidding. I keep saying that and her eyes roll out of her head. Well, I'm excited to jam with you because you've had such a unique career in the sense that like you've done the IC rules. You've done like multiple levels of leadership where it's like the frontline leader type of thing, the second line leader, like leading a sales organization.

5:34Now you're doing some really cool stuff. I don't know. Do you call yourself an advisor now? Like what do you call yourself now? Yeah, I have a title of head of sales strategy, which is totally made up, but effectively an advisor operating partner. Yeah, and it's like you guys have 150, you know, vertical SaaS companies in the portfolio. So you have this like really unique vantage point where you've seen how a lot of like the inner workings at an organization looks like. And there's like some pattern spotting there. So I want to just backtrack a bit for those that maybe didn't listen to that episode five years ago.

6:09So you were living in the Virgin Islands and you were not in sales at that time. So tell us the story of how you kind of got into sales from there. Yeah. So I was living on St. Thomas in the Virgin Islands. I had just graduated college and didn't know what to do like most folks and said that would be fun. So I moved out there and I was working at the Ritz-Carlton Hotel. I also worked at another fine dining place in the evenings. And then that place would turn into more of like a lounge and closed down dining. And I would DJ that place until like three o 'clock in the morning. So I was working three jobs around the clock, man.

6:49And it was a lot of work, especially with the Ritz-Carlton, because out there, you know, employees are hard to come by. Like there's super high turnover. People come and leave. And so it wasn't uncommon that I was working double shift 12, 13 hour days there and then going on. So I was working my butt off. But on the days I had off, man, I was living in paradise and it was nice. But my foray into sales from there would be, you know, essentially I had these President's Club winners from companies like Edward Jones Financial. I'm trying to think of what other ones. But basically these guys that would win their president's club, their company would send them out to the Virgin Islands for a week, put them up at the Ritz-Carlton.

7:33And I would spend time with these guys because I have guys and gals. I'd be serving them at the pool and on the beach and all that. And there was always a job offer in it, right? Like, oh, man, come back to Indiana and we'll teach you how to do this. And, you know, eventually I just had this realization of like, man, I am on the wrong side of this equation.

7:57for not that so you knew because you said your dad is in sales so you knew what's like sales was and all of that kind of stuff or no yeah my dad is a little more of like the old school relationship handshake uh seller which is which is fine like that's how that's what how it was in his day but he goes all the way back to i mean he sold uh uh blue printers for building designs building building in new york city yeah back in the day that's where he comes from so he's probably done a lot of door-to-door and what I would imagine is the hardest place in the United States to do door-to-door. Yeah. Door-to-door, building to building.

8:33Yeah. So they were talking about sales. What was like the spark where you're like, okay, cool. Let's start looking into this. Was it a SaaS role? Was that your first sales role? Yeah. How do you connect the dots there? I don't know that there were many dots connected there. I think it was kind of like, I had two places in mind I wanted to to live which was uh uh basically anywhere in Colorado and then Austin because I had some family here and so I applied to jobs all over um ended up getting uh the job a job in Austin and um you know sold everything I had and moved out here to start yeah so how are you feeling in that moment were you excited were you a little scared a little bit of both I was excited but man like life is different when you got nothing to lose it's far more comfortable to do things like that right so like i think at the at the time i was not in no state of panic or anything like that um certainly i would feel differently about it today yeah you know it's funny you mentioned nothing to lose because uh john who i was telling you about the cro at oram yeah i had him i was with him yesterday on the pod and he said that that's something that he looks for in kind of the backstory for a lot of the reps and leaders that he's hired over his career.

9:56It's the people that are just they're so passionate about and they want to get into it so bad. It's just like there's no other option for them at that time. Yeah. So you move to Austin. What's what's that like? Walk walk us through like you roll in. What happens next, dude? Yeah. So I think I started to tell you this story, but kind of a funny story. I had been working with this recruiter to get this job um and between the time that I was basically got the job and moved to Austin this recruiter had completely gone dark on me um like wasn't responding to emails wasn't responding to anything and I moved forward with my move again I sold everything I had packed up my car rolled into town I was living on a family member's uh guest bed basically so I hadn't found anywhere to live.

10:45And it was the weekend before I was supposed to start on Monday. And I'm like, I don't even know where this company is. Like their address isn't online. I can't find a contact number. So then I guess I was pretty panicked about that actually. So my brother-in-law was like, I think he's a professor at UT. He's like, I think I have a student who mentioned they had a friend that worked there so i literally followed like practically this cold calling chain of like hey do you know somebody part of their selection process yeah it was all a test um so i ended up getting a hold of somebody who worked in ces and was just like man i'm sorry that happened to you here's our address and good luck um so i showed up monday morning and they were not expecting me like the ball had completely gotten dropped oh so what happened is the recruiter had gotten fired of course and nobody let me know nobody was expecting me and so it was decided like I guess we'll take him anyway so yeah I still have the job got started you know jumped into training became top rookie of my class right off the bat and really got up to speed quickly from there Okay.

12:06So you land the sales role. You do really well. Why, like, did you ever think about taking the leadership track? Or were you, like, focused on being an IC for a while? Like, why the leadership track? I was focused on being an IC for a while. I had another couple roles until leadership was really compelling to me. But I have to think more deeply about that. I would certainly say a big determining factor was somewhere along the way I had my first child. I was pretty young, which changes, I think, everybody's perspective of who they are and what they can accomplish and what they need to provide and who they want to become.

12:50And so that was probably a really large part of it for me was, you know, kind of being dropped on my head into that experience. So leadership you saw as a way to have a, what, a better financial future potentially for a family and stuff? Better financial, also probably like, I don't know if the right way to put this is like a better sense of purpose, but like a stronger idea. Because, you know, it could be hard as a sales rep. I think everybody has felt that feeling of being sort of expendable, especially if you're in a sales organization where people quite literally are expendable and treated expendable.

13:29Yeah. So I think, you know, striving for something a little more anchoring is probably part of that, too. It's funny that that's your perspective because the average VP of sales in SaaS, I think, lasts like 12 months or something like that. Yeah. You know, so it's not exactly super stable there either. Yeah, I'd agree. Okay, so you go to the leadership track, you have a ton of success at Qualia. I think there was another company maybe between there and what you're doing. Yeah. So how do you end up doing what you're doing now, like really advising a lot of the companies? And feel free to talk a little bit more about like what you do now and like types of companies that you guys work with and that sort of stuff.

14:11Yeah, so I'll hover for a second on Qualia. um qualia was a role where i literally joined that role telling um telling our sales leader like hey i want to be in leadership before before day one um and so that was sort of um the opportunity was there but the test was come in and earn it type of thing yeah um so i joined qualia in the first like 30 employees super early on the first class in Austin and became top seller on the team within the first year. I think I closed like 60 something platform deals in the first year. Earned a promotion there. And really, since I was one of the first people to be finding tremendous success, that shaped a lot of the processes and the coaching.

15:04And so I was just organically spending a ton of extra time coaching other people up. I would come in seven o 'clock a.m. early. I would spend my lunch on other people's demos. I would stay in the office late as a rep. Yeah. So that's a really good example of you were doing the job before you were hired to do it. Oh, for sure. Yeah. And that was the expectation. Like, you know, I was told there's no way I could promote you to a leader if you're not at or above quota. um and so this is something i share all the time like if you're someone who's aspiring to be a leader you really do have to put that oxygen mask on on yourself first to make sure because that's this is my problem i know this wasn't a topic we want to talk about today but the the seller um what do you call it this the seller coach model i have a big problem with that generally because almost always the performance goes out the window from the seller.

16:01And that's what you're referring to as the player coach model. Player coach. Okay, just making sure. So this is actually a pretty good thing to talk about because I think a lot of very big organizations still do this, where you have like a team lead who is expected to do a large part of the sales manager's job, which I'm wondering, what do you have in the sales manager do if you have a sales manager for a team and a team lead who they're asking to run some of the one-on-ones and stuff i'm like what's going on here um let's spend some time on that what why doesn't that work in your experience i think there's a number of things but the main one that jumps to mind is just like performance you only have so much time right and performance almost always outweighs the desire to be helpful.

16:51Like even with the best intentions, if you give somebody who wants to be a leader and say, hey, yeah, do all this extra responsibility, they want to do that. And they're probably actually really helpful and really good at it. But the problem is like the performance almost always takes a dip. And then the excuse is, well, but I've been spending all this time with all these other people. Yeah. And so. I do think there has to be somewhat of a hard expectation set like like was set for me to really be able to do both, like maintain your your position as a top seller on the team and keep putting up the revenue while doing extra like, you know, a huge percentage extra.

17:37Like I said, I was coming in first person in, last person out, spending my lunch and everything in between. Don't talk to me. Yeah. Because I'm in my lane. Yeah. So are you of the point of view then that you probably shouldn't do a player coach model or is part of it also just being really clear and upfront about the expectations or is there kind of room for both? Like, do you have a strong stance one or the other? Yeah, I think there's probably room for both, but with like clear expectations. I'm extra clear expectations because I'm someone who's always led. I always say, like, I only want to lead leaders.

18:15I don't care if you want to be in leadership. I expect everybody to be a leader. So, like, you know, I would definitely have people on my team and say, hey, I want you to run the stand up this week or like, hey, I want you to help do this. And that's a way to help coach and develop people, even if they don't think that they're good at it or they can handle it. They definitely can. But I think that's different from lowering the expectations at expense of doing all these extra things. Yeah. So let's talk about, because one of the things that we do want to talk about is kind of managing the org a bit.

18:56And I think this is really relevant for like how you think of the org, how you set it up, like the day to day management, et cetera. Let's spend a little bit of time on this topic. Like I'm curious. With your experience and now with a lot of the companies that you advise, this whole idea of, hey, as a sales manager, I want to work with leaders. and just because you don't have leadership or manager in your title doesn't mean that you are not a leader and a part of that is like this attitude and like value yeah on your team around like yeah i'm not going to run all the stand-ups in the team meetings this is really sort of the exact opposite mentality that a lot of frontline leaders have yeah where they want to do everything including helping close the deal and like all of this other stuff so can you talk about kind of the mindset and approach around that and just other kind of practical ways that as a sales leader, I could be thinking about how to set up a system where my reps are like really empowered to lead.

20:01Yeah, I think of it again as sort of the same way because I've asked I've been asked this question every day and I'm sure I will continue to be because people want to aspire to leadership. They say, how do I get there? And so as you mentioned before, like part of it is doing some of the job before you get there. And so like one example I'll give you is like, this is a relic of the in-office days, but if you've ever been sitting on the sales floor and you realize it's dead quiet, there's not a single person on the phone. Yeah. It's one thing if your sales manager, director, VP comes in and says, everybody get on the phone right now.

20:40What are we doing? And, um, but it's another thing if as a rep, you say, Hey guys, it's dead quiet in here. Like, let's make some calls. Yeah. Uh, you know, 20 bucks to the first person who gets a demo set against me, you know, that, that sort of thing is what creates a culture of, of people who are driven and sort of self-leading to better results versus like their, their manager coming in and having to crack the whip. So that's just like a small example of like anytime someone says, hey, I want to be a manager or I want to be a leader. It's like it starts by just leading. It's not just a title or a job promotion.

21:18It's like you're either a leader or you're not. Yeah. If I gave you the title and you're not leading, nobody's going to respect you. Yeah. And it's this idea of like it's like positive peer pressure. Yeah. It's like if my peers are doing something, that's a lot more powerful, like you said, than your CRO or VP coming in and just yelling at everyone. Exactly. So how do you like if you were advising a sales leader, you know, around how to create some of these future leaders and how to identify them? How does that how is that typically worked in your experience and what would be best practice around, you know, for example, like, is there something very strategic and intentional around like, hey, like, here's who we think on the rep side, our future leaders might be.

22:04and like, let's plant the seed and have those conversations. And like, how do you kind of think about that from a strategic standpoint? Cause this is like a huge need as the organization grows is thinking about like, where are our future managers gonna come from, you know, our future leaders. Yeah. So I think like a blanket statement that I'll always just put out there is you have to just lead. Like you can't wait for permission. You can't wait for me to tell you to do it. Like if you're not just leading, like I can't. nobody's going to do that for you so yeah anybody who's expecting to kind of like level up in that regard has to be willing to do that in and of themselves yeah on a more sort of tactical basis i think kind of going back to the oxygen mass story there's things that you need to personally have excellence in that make you in any way shape or form qualified to be a leader um so you know quotas some you know oftentimes the end all be all although a lot of leaders are promoted you know because they are they know the product or whatever but they may not be actually a quota achiever most of the leaders that i've met the very successful ones weren't like the president's club you know they might go to president but they weren't like the top reps right usually and and and suffice to say like not every president's club winner is most of them are probably not poised to be great leaders yeah but one i think is overlooked is like uh pipeline hygiene right what is your job when you're a leader your job is to make sure you're you're doing pipeline reviews you're making sure the pipeline math adds up to quota you're making sure the hygiene is there so the numbers you're looking at are actually telling you something and um what's kind of funny is i i have managers who come to me and they say hey i want to be a director now what do i have to do and i think my my attitude about that is everything just scales up you go from managing your own pipeline to a t keeping everything organized keeping everything updated um staying on top of all that to a sales manager now you're doing that for five six seven eight people yeah scale okay and you go to director of sales now you're doing that for two three sales managers who have five six seven eight reps underneath them so like the skill set there only scales up and if you're a rep who thinks that it's an an annoyance or why do we have to do that like how could you ever be yeah tasked with holding people accountable and and ensuring that the numbers line up the forecast lines up to hit targets yeah you're the person trainer that is running a workout class that's out of shape at that point, right?

24:55Yeah, it's a good way to put it. So in terms of like, can you walk us through actually, because I think this will give some context into this and some of the other things that we're going to talk about. Some of the work you're doing right now, like, can you talk about the types of companies and like the stage of these companies? And then that'll kind of, I think, gear a lot of the questions. Yeah. So within the venture studio, we have about 150 vertical SaaS companies. At this point, their life cycles are all very different. We have some companies that are series A's. We have some companies that are seed or pre-seed, and we have some companies that started two months ago type of thing.

25:39And so the inflection points are all a little bit different, But suffice to say, like my my general work has been working with founders who have maybe, you know, figured out how to get the first dozen customers by themselves. They have maybe 500 K and A or R. Yeah. It's the typical everything lives in my head because I figured it out as the founder. Are they doing all the sales too? They're usually doing all the sales. Yeah. And so a huge focus of my work is basically helping them take all that stuff in their head, put it into a real foundational sales playbook. Yeah. And I always phrase it as something like you need to be able to actually hand this to another person.

26:22Yeah. In a way that they can run with it and be successful. Yeah. We talk about how that becomes measurable. But so usually getting that in my head stuff into a sales playbook, helping them figure out who's the right person to hire for this role, helping them hire, helping them train up, set the targets, compensation plans, everything in between and scaling up from there. So let's dig in. We're going to go a little off from what we talked about before, because this is like your sweet spot and your zone of genius. Yeah. So I would love to talk to you a little bit about this kind of like zero to one.

27:00When I say zero to one, like zero sales reps to one sales rep or your first set of sales reps. There's a bunch of things in there that I think at those different stages that will be interesting and helpful to others. So how do you advise founders on, hey, I've done all of the sales. It's founder-led sales. I'm closing all the deals. I'm about to like build out a sales team. what's the move there? Is it I should hire an account executive or two or three or whatever might be to start doing some of the sales? Is it no, maybe I should bring in a head of sales, let's say, that has experience at this level that's going to be doing a lot of the sales themselves, but like someone that can kind of own the sales department?

27:47What are your thoughts? Is it something else? Like what are your thoughts and philosophies around like it's time to build the sales team what's next. Totally. I think my answer is there's a right way to do it and then there's everything else. Everything else spans a spectrum of everything you just mentioned. And I will say for most founders, it's well-intentioned. It's the best intentioned. It's what they've heard other people have done or they've seen it on LinkedIn or whatever. So a couple flavors of that that you mentioned is like hey i got a dozen customers like we just raised the seed round things are seem to be building traction i need to hire a seasoned uh vp of sales to like now blow it out of the water um but this person has never taken any of that stuff that they've learned and put it into process and for for the companies we work with uh for the vertical companies a lot of that is actually like industry depth of industry knowledge as well oh i bet yeah um in in addition to any sort of sales processes and and things like that um so that's usually that's usually a strikeout i mean i think of the vp of sales role as uh somebody who's pouring gas on the fire not lighting the spark and so a lot of in a lot of cases this is sort of you know call it lighting the spark or maybe it's like a little pilot flame but it's still it's not there yet yeah The other one that you mentioned is, okay, I have a dozen customers.

29:19This is going really well. Now I've got a pipeline, so I don't really have time to go out and find more pipelines. I'm going to hire two or three SDRs who are just going to set meetings for me. That also usually tends to be the higher, you know, two, three super junior SDRs and throw them in and see what happens. And these folks need so much hands-on work. And it's like, as a founder, you're not going to be doing, like, we had Ashley Kelly a couple days ago on the podcast. She runs sales development at Rippling. Yeah. They have, like, over 400 SDRs. And the thing that she always says is SDR is a daily thing.

30:00This is a daily business. And it's like, as a founder, if you're not giving those SDRs, like, daily coaching support, they're answering stuff. It's like, dude, they're not going to succeed. Yeah. They just aren't. they need the hand-holding, they need the structure, they need a lot more. So suffice to say, like, that's a failure mode for sure. So going back to what I think is the right way to do it, I think the right way to do it is to spend considerable focus on getting the sales playbook as tight as possible. And sales playbook is this sort of amorphous term we all use. Yeah, what does playbook mean to you?

30:35Because it means so many different things to so many people. Some people, it's like a 50 page Google doc. Some people, it's like a notion thing. Some people, it's like we have stages in Salesforce. You know, I'm like, that's not a playbook. So, yeah, what is it? What does it mean to you? Yeah, I think in my mind, it's kind of everything. But there's certainly like four or five core things that kind of lead the charge there. The big ones that you hear me talk about all the time are a cold call script. and we could debate scripts all day long, but it's your messaging. It's who do we talk to? What do we talk to them about?

31:12How do we talk to them? And how do we qualify to make sure they should come into our pipeline? That is the tenets of the words that are in your script. And if you don't have those things figured out, you're in trouble. Same thing for the demo. Who do we talk to? What do we show them? What questions do we ask? And everything from there. How do we set next steps? How do we talk through pricing? That should all be in your demo script as well. And end to end, like if you just did those two things alone, you're like probably halfway there for being able to pass something on to somebody else. Yeah. But some of the other things, of course, are like common objections and rebuttals.

31:50Your hiring profile, like before I put butts in seats, what butts am I looking for type of thing? What are we going to pay them? How are we going to pay them? What sort of quotas and metrics will we have for them? How many of them do we need? So the, you know, the headcount modeling, all of that, I think of as part of like putting together this comprehensive sales playbook before you even make that hire. Yeah. And my guess in the companies that we work with are not always quite at this stage. They're usually like they have a sales team already. Yeah. My guess, though, is that most folks start hiring before they have any kind of playbook.

32:29can. Yeah. Yeah. So documenting that. Not if I can help it. But yeah. Right. Yeah. I imagine what is really awesome about what you guys do is, you know, having someone to work with like yourself that can help with that playbook, because a lot of the founders are, you know, some of them might be a little bit more technical or have no formal training in sales either. So they've never maybe even seen what a playbook looks like, you know. Totally. Yeah. OK, so I have this playbook. And And in terms of like the first round of hires, I don't know if you've seen some of the stuff on LinkedIn lately around like the founding AE.

33:03And then like, oh, is that able to tighten there on the right? Is that working? Let's see. There we go. There's a lot of talk on like, oh, this founding AE role is like, hey, the compensation is going to be very different for this because this person needs to be much more autonomous. And like, because like the kind of stigma, I guess, around being a founding AE is that, you know, oftentimes there's two things I've seen. One, it's a BDR who has zero sales experience that they, you know, poach from a really well-known, respected company, but someone that has zero sales experience. Yeah. So you have that person coming in or they're like, hey, I'm going to recruit like a really veteran person that like really understands this.

33:46And really a big part of their job is creating the sales process, which from what I'm hearing is a big no-no. I don't want to bring someone in to build that process. So what does that look like? Is it I bring in one person? Do you have a role where we're going to bring in at least a couple, two or three? Does it kind of vary based on the circumstances? What should that first round of hiring look like typically to set yourself up for success? I have my opinion of it. Yeah. My opinion of it, I think you've touched on, again, some of the things that you're at risk of, which is one like far too junior on the SDR side.

34:22I also am a big believer in, this will probably get me in trouble, but like seniority or time in sales does not equal skillset or impact. In fact, in a lot of cases, the further we go out in timeline, the less impact I tend to see. So why do you think that is, by the way, just for people that might be thinking, oh, this, I run a construction SaaS. a vertical SaaS, oh, this person's got 20, 30 years of experience in construction. Like, what is wrong about that thinking, I guess? Or where might they be overestimating this person's skill set?

35:06I'm trying to think of the correct way to say this so I won't land myself in trouble. I think the obvious things are longer tenure usually means older in age. Older in age usually means less inclination to risk. So for early stage, like some people thrive in startups in the early stage. And like myself, other people have been working for Oracle or Dell for 20, 30 years and have a big family and a mortgage and a boat and whatever they have. And we're like, why would I jeopardize that going to work for a startup? So the risk tolerance isn't there. The other one is like if you are that long in sales, you've probably been a part of larger organizations where you're accustomed to far more resources.

36:01whether that be systems resources uh marketing assistance big brands and all that that you just don't have at the startup level and you know even again the most well-intentioned like senior people who are like yeah i'm looking for a new start i want to go do something where i can have high impact they find themselves like completely underwater because they didn't know what they didn't have yeah uh or i guess they maybe took for granted for what they did did have um and then the the other one this was the one that was going to get me in trouble it's just the cost um yeah like you can this is my opinion again but you can fail in a role every year let's say you do your six to nine months ramp period at a new company every year and by that six to nine months you haven't ramped things aren't going well and you either quit or you get fired you can go and get a job at a raise and do that every year for 10 to 15 years it's kind of crazy it's crazy and people do it yeah so next thing you know your your lifestyle is a 200 300k lifestyle yeah but your resume is a six to nine month stint every year for 10 to 15 years yeah so that's like a bit that's a huge red flag i look out for on the hiring front but um you know obviously only really applies to people who are have more of the seniority yeah so what's the right move then so the right move or at least my my recipe for this is i look for folks who have call it one to five years full cycle a experience.

37:37The reason why is at this stage, you know, for the founder, they should expect to do a lot of handholding, but I don't want somebody who this is their first time touching Salesforce or HubSpot, or this is a first time talking to a business owner, first time closing a deal. If you have the capacity and the will to like handhold all those things, great. But let's assume that you generally don't yeah you're not going to yeah i'm looking for the people who have like done a year or two where somebody else did that yeah and now they're like the wiggles are kind of out but they're still junior enough to be driven have that grit um you know they want to to grow they want to be coached they want development all that sort of thing kind of comes in that area and then again um you know just brass tacks on was a person like this cost they're far more like affordable for early stage company running on a fairly lean runway um can't afford these 300k 400k inflated ot's got it yeah and would you recommend that a founder brings on multiple people at the same time to just kind of hedge their bets a bit totally this is actually maybe profoundly unprofound but um i think a lot of founders i talked to think that when they hire a cohort they expect everybody to hit quota like everybody to work out and it's such a fundamental flaw in their modeling yeah because just like it's just not realistic if there are people out there who are hiring cohorts that everybody is successful kudos to you but it's just it's just not really yeah I mean I would say like in my career we we always hired cohorts of probably four to six and we'd be lucky if one to two work out and the other especially the first round I would imagine because there's so much so many unknowns yeah absolutely yeah so uh I definitely I mean at the bare minimum I always recommend hiring at least too because then you have benchmarks yeah right and that's that's another sort of um gray area that i tend to see with folks is they'll hire one seller they don't get really clear on what the ramp expectations are yeah and so again six to nine months later i'm like how's your seller doing and they're like i'm not sure yeah like we really like having him or her on the team They're a really good culture fit.

40:17They seem to be building like, you know, some good pipeline. It's like, okay, but what does that mean? Like, are they at their pipeline goal? Are they hitting quota? No, but I don't know. And then you do another cohort or two and you realize there are people that 100x what this guy did over six to nine months. And so at a bare baseline, like two people gives you an A-B test for the same ramp. if I put two people in, which one comes out 20, 30 % better than the other one. Yeah. And like that to mention, like when that, if you hire one person, that person doesn't work out how far back that can set you when it's your very first time that you're doing this.

40:59And I think a big part of it too, is the, it's just the mindset and the mentality and how demoralizing that's going to be. Yeah. It's rough. It's also a reason why when it's not working out, there's a fear to cut ties with that person because it's the only person it's all we got yeah so the other big benefit i'm a big believer in this uh to hiring at least two people is they can actually take a lot of the burden off of the founder for just like uh reps at things like they could practice cold calling each other they can practice demo each other they can spar all day they can yeah practice flash cards of objections and rebuttals with each other um and that's that's a huge like lift for just if you're a founder who's still running demos still running pipeline while also trying to get somebody else up to speed it's much easier to like spend an hour with them and say okay you guys go practice and we'll see you at noon versus like they're just sitting on their hands waiting for you to finish your demo yeah not to mention if i'm a rep i want other reps to compete against dudes yeah there you go um yeah let's spend a little bit more time in the hiring profile.

42:09Is there any other maybe counterintuitive things or non-obvious things around hiring or how you like test people through the hiring process? And I ask that because, you know, we've worked with some big companies on the BDR side, especially where I'm like, you're not having them do a cold call role play during the interview process. Really? Yeah. That's wild. Like, one of the things that we'll do and we're a much smaller company and I don't run a big sales team anymore, but you know just giving people test projects it's like hey we're not going to hire you yet as a as a trainer let's say we're going to work with you as a contractor and put you on a client and like test working with you to see if it's a mutual fit you know and I get that maybe you can't quite do that in sales where you're going to say hey I'm going to have you work a deal or two while you maintain your other job but there are other ways to sort of test fit sure but yeah tell the hiring profile is there anything else there to like really double down on and in terms of like testing fit what is what are your what's your guidance there yeah i mean within the hiring process one thing that like if i were to do only one thing and throw out everything else it would be the mock cold call yeah um i think everybody has their own kind of flavor for how they hire and um certainly the more you do it the more you develop your own sense spider senses for for who you want to hire but um i my my particular method there is i want them to pitch me what they sell today versus a lot of folks will give you a script and be like pitch us our company and they want to see how quickly can you learn it and all that but for me i want to hear what you've been doing day in and day out for the last year or two or three or four or five and if it doesn't sound like you are good at it after five years you're not going to be good at it here yeah like it's it's really that simple you can tell somebody who does their pitch in their sleep and somebody where it feels awkward and stumbly and fumbly and they're not sure and that's just such a dead giveaway for me yeah and it's really interesting because over time i've had people who have blown me away on like the panel discussion like questions and then completely bombed the the mock call it's like they couldn't string two words together and vice versa i've had people who were like a little bit more timid a little bit more shy maybe nervous in the panel and then you get on the mock call and they're just a killer they're just dialed they are so dialed like they've been doing this in their sleep every day yeah and yeah so if i were to like keep one thing that would be it for sure um a couple specifics how do you prep them if at all for the mock cold call in terms of like you give them like a hey here's what we're going to do tomorrow you're going to be selling your product or calling this thing um what kind of prep do you give them and then two like how do you actually do the the role play and like what are you what are you specifically looking for or grading or how hard do you make it like all of that kind of stuff yeah so suffice to say i've been doing this so long that i have become like an improv professional i can play any prospect you throw at me and i will give you nightmares about how how like realistic i could be as your prospect but there isn't there isn't a ton of structure i don't give a ton of structure on purpose because again it's just like pitch me what you pitch every single day and i always say the goal is not for you to set a meeting the goal is for you to help me understand that i might actually need what you have yeah to find pain in in the most basic sense right yep um so the objections as any and you know improv-ing any persona are always the same like we're all good we're set we don't need this we've been doing this for forever we're good the way we do it why would we do it differently how much does this cost send me an email all the hits all the things you've ever heard and again like somebody who's done this day in and day out doesn't bat an eye at the everyday stuff yeah so you put them through the ringer dude yeah yeah i love that but through the ringer of things that it like nothing that should be out of out of the norm of what they're doing every day.

46:30I just feel like what's a role play, people just give them super easy role plays most of the time and they don't really give them too many objections, you know? Yeah, yeah, yeah. The hits, though. Yes. Send me an email. I'm not the right person for this. How do you test for coachability?

46:47And is that important through the hiring process? Oh, it's definitely important. Honestly, it's something I should focus on more. I would say I can count maybe one or two times in my entire career oh here so let me let me answer this first after every mock call I always do a feedback session yeah I start with the candidate doing their self-feedback usually what are two things you think went really well what are two things you you think you would have done different I want to see what how they basically self-coach how can they be introspective that tells a lot and then i will give my feedback and whoever else i may be interviewing with will also give our feedback and then you can kind of gauge the response if they're like wow that's really really good super helpful that's that's a good sign if they become defensive or they're like well i disagree um yeah probably not a good sign but I was going to say I can count maybe one or two times ever that I've ever given feedback to somebody on a mock call and they said can I do it again and then actually turned around did a better call yeah super rare which is the ultimate sign that someone is not like because being coachable to me is like two parts it's and maybe it's three actually it's one I want to be coached like you want people that will not work at a company that doesn't give them coaching um i think two is being open to the coaching and then three it's being able to implement the coaching yeah so asking for that second chance and then crushing it is like that's like someone that does like okay the first time around takes your coaching and crushes it the next time like i would almost prefer that person yeah you know you have to crush it they just do marginally better yeah than the last time and it's a good sign for sure this is something i feel like is so underrated you you have to touch test for coachability and just you want i've seen these teams that are so great where the entire culture across the board is coachable and people are open and they're just receptive and i've seen the exact opposite and it fucking sucks dude when it's the exact opposite absolutely yeah um i think it all comes back to you know i don't know how much we're going to deep dive on on the the seller side of like what it's like to get a job but uh you know it's not you don't just get a job you You got to earn a job.

49:12And I think that's part of it. When you're in the interview process, you have to do things to show that you're coachable, to show you can grow, to show you can learn. And that's a big one of them. I have another org type of thing that I want to ask you in terms of timing. So if we jump ahead a stage or two in maturity, and it's like, I've hired this first round of account executives. They're doing good. I have a couple of people on the team and we're going to keep growing the sales team. what tends to be the guidance around the order of operations from there? Is it, okay, cool, let's bring a manager in to like manage these folks.

49:49Is it, I should start thinking about looking for a head of sales? And if not, like when is the timing usually good for a head or VP of sales? And like, how do you suggest through that like series A, series B, kind of the later stage clients in your guys' portfolio, like how do you typically advise them through the growth of their sales work and the order of operations there? That is a really good question. I will give you, again, my firsthand account anecdotally of what I think is an answer that maybe a lot of people aren't trying. I'll give first the two polarizing, like where I see it not working.

50:27We all know the VP of sales thing too early tends to not work out. you know early on especially if a founder is handing off a team that they've built yeah you still need somebody who's hands-on in the deals what's too early mean to you by the way when you say that um i would say well i think it comes back to the profile of this vp of sales like a lot of vp of sales um are maybe they're more senior and maybe they've been afforded having a line of directors and managers and people beneath them and can, you know, I'll use the expression dash can be a dashboard VP where, you know, they're doing important work of managing the forecasts and overseeing quotas across multiple departments and things like that.

51:16But that person, I don't think thrives when the need is, I need you on like all of the big deals with every single rep and I need you doing pipeline reviews and I need you actually call coaching and doing all that stuff um and then the other side to that is is just to like not senior enough like somebody who's a good early rep gets promoted to like a team leader manager and they're doing the best they can they just don't have enough of the experience to really like make the most impact and the founder is maybe not equipped to develop them in that way so the the profile and i i've seen both play out many many times within our portfolio lots of first vp of sales failures in fact um the profile that i actually recommend these days is more of like your director of sales level yeah where they are still close enough to coaching hands on the deal they love being in the trenches they love working with the reps so they can provide all that.

52:24But they have a ton of potential and upward mobility to be more strategic and lead bigger initiatives, own a much bigger number, and effectively earn their way up to a VP title or whatever you want to call it within a year. And so we're actually seeing pretty good success with that profile for an early stage company where they can basically hire somebody who fits the immediate need, but then also has the potential to grow into the department head. Yeah. Which makes a lot of sense that you would want someone that's super hands-on. And again, that's just not what I see oftentimes where I'm like, okay, this person would be a great VP if you had a hundred reps.

53:04Yeah. But they haven't cold called in a very long time. They're super rusty, like hopping on sales calls, like that kind of thing. Yeah. What are your thoughts on over titling so like bringing in the person that like fits this role let's say and then giving them like a cro title or an svp of sales title i think it's pretty rampant and i'm actually a big believer in titles um some companies take it very seriously others are like yeah what do you want your title to be and uh maybe i'm a hypocrite because my title's made up but my role also like my role also like doesn't really exist in most other places i think it's a it's a rare exception But I think it matters.

53:48I really think it does. One of the things that I, you know, I'll just give an example. One of the things I advise all the time is like people want to give like an AE or somebody a little bit more responsibility. And that AE might even say, OK, I want to be the head of sales. And the founder's like, yeah, whatever. I'll make you whatever you want. Just do this role for me. um the problem the problem and this plays out like almost every time is what happens when you reach the stage that that person needs someone to learn from needs development from a senior leader and you hire a VP of sales what automatically happens head of sales gets demoted yeah they're not pumped about it um so there's a little bit of like the sort of just um uh ego portion of titling that like if you inflate too early eventually somebody's going to get yeah virtually demoted and and it can be really deflating and it and it can cause people to leave your organization yeah um so i i think it's better to be a little bit more cautious and give people the opportunity to earn the title they want but it has to come with clear criteria of like what gets you there what gets you to earning this title yeah and then there's also this like hey I have this person who has a VP role that's really a sales manager.

55:11Yeah. Let's say. And then now there's the comp with that. And it's like, if I have the VP title, I might have some expectation that I'd be compensated like a VP instead of a sales manager, which is unfair to the business. Yeah. You know? Yep. I had somebody talking to me the other day. They're interviewing at a company and they were just wanting to get my thoughts on the companies they were talking to. And he was like, this one I'm talking to, I'm interviewing with the CRO and they're hiring their first salesperson. This would be their first salesperson. It's like, why do they have a CRO and they're hiring their first salesperson?

55:48The reality is like, who knows what the CRO actually does, but somebody gave them a CRO title. Yeah, that's crazy. um okay so we've talked about the hiring progression kind of like the the org structure and the different kind of levels and stages and how to think about that yeah um next what i would love to talk to you about is like setting like the the sales math and like the forecasting kind of components of this So a lot of the companies I'm assuming that you're talking to, and we've sort of briefly talked about this, they're probably given a target, right, by their VCs or whoever. They're given a target or it's been kind of predetermined for you, at least as the sales leader, right?

56:39It's been dictated to you. How do you think about, like, setting the individual quotas? And is there any high-level kind of guidance around that? and then this is I know a whole nother separate topic that I might be lumping into too here but the forecasting components of this just outside of like you know hey yeah like we fill out a google sheet and do this or we use gong to help us with this or whatever just like common mistakes with like setting targets and like forecasting and stuff would be great I would love to talk about this I'd actually like to go back to uh slightly a different part of this the discussion because I think it is a good sort of precedent here.

57:22When I moved on from Qualia, our CEO had said, hey, I have this thing that I think you'd be really good at. We could use someone like you at. And that was the Venture Studio, which I joined temporarily and now have been at for three years. But initially, I was just like, no, no, no. I had in my head I wanted to be a team leader, continue being a team leader. and um so over a period of like three months I probably interviewed with a dozen companies for VP of sales roles and I was blown away with how unimpressed and confused is probably the right word for it how confused I was as I looked at the number on the paper they were giving me and then asked for their metrics, asked for their conversion rates, did the math and said, you know, I have a snowball's chance in hell into hitting this number this year.

58:22Why would I sign up for this? Yeah. And I was just so, now I know that it's just like all too common that people are not working the math. But I was doing that for myself to vet the role and come to find out the majority of the ones I talked to were just like the math did not line up to the targets and it was a suicide mission. And fortunately, I recognize that. So I'm glad I ended up going the route that I did because in the work I do every day now, I'm helping people make sure that the funnel math checks out for everything that they do. So backing into your question here, like, yeah, you might be given your target.

59:03It might be pressure from your VCs. It might be an aspirational target. And you can always take the bottom, the top down, which is basically taking your target and reverse engineering the math to what do we need to be doing on a pipeline level, conversion rate level, and all that. With pipeline, do you believe in pipeline coverage and all of that stuff? Yeah. I have pipeline coverage tattooed on my back, man. I'll show you after this. I'm just kidding. Yeah. Show us your tattoo. Tell us a little bit more about that piece before you go on because you know what you'll hear a lot is like pipeline coverage is bullshit you know like that and then you hear folks that like over index on pipeline coverage or you hear something like yeah we need 3x pipeline coverage and like where'd that come from you don't have a 33 % win rate you know um so just thoughts on pipeline coverage and that kind of concept would be great yeah so like I said before like as you move up in in in seniority in sales roles, even all the way up to the founder, everything just scales up.

1:00:08But if you scale it all back down, it scales down to at the individual rep level, what pipeline coverage you need to hit your piece of the target. And so I mean, I'm a huge believer in pipeline coverage. I think it's something that should be screaming in your face every minute of every day so that you're painfully aware of what you need, because you can lie to yourself and say, I feel like I'm going to hit my number i'm feeling pretty good but the math of of the funnel math is literally statistics yeah if you uh have we'll do some back in the napkin math here that i always use if you have a 20 conversion rate from a meeting set to closed one which is which is a good healthy conversion rate that means you need 5x pipeline coverage to hit your quota right um so uh if you have a better conversion rate you need a little bit less if you have a lower conversion rate uh you need more for sure like if your conversion rate is sub you know sub 20 if you're at 10 you need twice as much yeah right and it is statistical math to say like you cannot fall within 10 % of a number at a quota if that number doesn't math to the quota.

1:01:34So yeah, this is one of those things where working with founders, I'll hear things like, I want to set this SDR, this AE's pipeline goal at like 12. Does that sound like too much? Does that sound like too little? What does that sound like? And my answer is always like, it doesn't matter what I think it doesn't matter what it sounds like we have to look and see if that is what gets them to quota and then we do the funnel math of it um but it is it's it's highly overlooked and it should be so fundamental and just so so clear and I feel like even founders should do a good job themselves of like being aware it's not communicated enough to the reps to really understand.

1:02:22And then I know we wanted to talk a little bit more about coaching, but there's also layers to this. You can do this at the team level. Take your team average, and that'll give you a good barometer. But at the rep level... Yeah, every rep's got different conversion rates, and some are better or worse at pipe gen, and some have higher or lower win rates, all that stuff. Right, exactly. So our blended average might be that 20 % conversion rate, and that might anchor our math for pipeline coverage at 5X. But then we splice it into the individual reps. Rep A has a 10 % conversion rate. He needs twice as many demos set as Rep B at the 20%.

1:03:04So I think sometimes it can get a little bit hairy there, giving different people different targets. Maybe it doesn't seem fair to do that. but the coaching piece needs to be hey our team average is 20 but yours right now is 10 you need to be setting twice as many demos as every as everybody else to hit the quota until you bring this conversion rate up and i'll work with you on that but like that's the math of it man you're not going to set the same amount of demos and hit quota as them it's just not happening yeah so love it let's um just because we had a little bit of time left yeah i would be remiss if I didn't ask you about some of the pipe gen stuff.

1:03:48Sure. That's working. So when I asked you this before, you're like, cold calling. Yeah, it works. I'm like, yes, it absolutely works. It's a bit of a different game. Yeah. You know, right now, of course. But what are you seeing across your portfolio and just in your firsthand experience of like, you know, pipeline generation methods that are working? Yeah. So, you know, I had mentioned to you, I have a bias in this in the in the sense that all of my work is focused on vertical SaaS companies. Yeah. And I think that there's a big advantage there. I don't know how much time we want to talk about that, but I've personally aligned myself with vertical SaaS because I think it's a winning formula for salespeople for a number of reasons.

1:04:30We can come back to that. But one of the advantages for vertical SaaS is you generally have the presence of brick-and-mortar office locations with people who work in them, and those are people you can talk to. So whether you're calling the business line and maybe there's some back office admin or operations folks or service managers or the owners there, like you have a way to pick up the phone and reach somebody. And I think that that is such a huge advantage for any salesperson to place themselves in. Because if you look at tech selling to tech, for me, I think it's some sort of special hell to have your job every day, like lobbing an email to some CMO or CTO for endpoint monitoring security, hoping I'm going to craft the perfect static words in an email and hope it's the perfect right time.

1:05:28That's like the only way I can get in front of them. So, yeah, going back to the point here, man, cold calling, it absolutely still works. No need to fight about it here. The results speak for themselves. I don't think a tremendous amount has changed in that regard. Like, I'm a big believer in the pitches all about them and the problems that they face. And if you're talking to people about the problems they have, a certain percentage of them want to fix that problem. And it's as unprofound as that. So from a cold calling standpoint, though, can you walk us through some of the block and tackle of that?

1:06:06Like, how are you advising, like, around tech, let's say, and, like, data? And, you know, if I'm in vertical SaaS, does it make sense to leverage some sort of data provider to get cell phones if we can? uh am i just calling into the brick and mortar am i using dialers you know like what what is kind of your guidance around that you know it's super funny that i i think i tend to fall on more of the old school um thinking around this because there's so many tools um it's a full-time job to stay on top of all the tools out there this is why we do not touch tooling really at all yeah i get tooling questions every day i answer to my best ability but i tell people like the tools reach further consolidation every day and they change every day and I just can't keep on top of it.

1:06:52So I think whatever tool works for you works for you. That's kind of my short story. But around data. Well, what's maybe the minimum viable tech stack? Like, are you recommending at least a dialer of some sort or some sort of, you know, voice over IP solution that I can dial from a sales engagement platform or something like that? Like, what are the kind of bare bones basics yeah i mean i don't want folks using their cell phone because then we can't measure it track it report calls like all of that's super important uh a number of our companies just use hubspot out of the box end to end yeah calling sequencing everything there obviously there's other tools that go deeper and they do ai enrichments and all of that stuff is cool if it works for you yeah but the thing about data providers in general people ask me every day like what data provider should I use?

1:07:43I don't know. I don't know what data they have. They all have different data. So, you know, my advice there is always talk to a number of them, get samples and whatever looks like the people you need to talk to, give it a shot type of thing. But I wanted to come back to this because I think it's important. I think the data providers and the general Sense has over-indexed so much to cell phones connecting with cell phones that we're like, we've almost forgotten how to engage. The gatekeeper. Gatekeepers. And actually, and as I mentioned, that's the biggest advantage in vertical SaaS. There's like 100 % pickup rate when you call a business.

1:08:25Yeah, exactly. They have to pick up the phone. Yeah. So, yeah, I mean, again, in vertical, you have just standard. You have admin people always. You have some sort of operations person always. If you're in any sort of trades, you have foremen and service managers and things like that always. They're always stakeholders to the sale no matter what. And then, of course, you have owners and other folks in there. Again, that's my bias. But one of the things that I actually can pinpoint when I look at metrics with folks is like if the conversion rates are not that great, oftentimes it's because reps are only calling one single contact on their cell phone and they're not calling the business line.

1:09:15They think it's a waste of time. Yeah. And it's like you have to multi-thread these. You have to talk to these people anyway. Yeah. It's the easiest way to get on the phone with them. Yeah. So just by multi-threading through the business line, your conversion rates go up. You set more meetings. You set more better qualified meetings because you have more stakeholders who are bought in. Don't overlook it. What are some of the metrics that you look at to determine whether the outbound calling is working or not? And I get that it can fluctuate depending on like kind of the vertical and, you know, the sales motion even.

1:09:54but what are some of the metrics that you typically look at? Are you looking at connect rates, like pick up to conversion rate into a meeting? Is it number of accounts that we've set meetings through? Like what are you looking at to determine if it's working well or where the coaching opportunities are? Yeah, you know, that's an interesting phrasing of the question because I don't think I've ever questioned if it's working. Like I think I just deeply believe that it works no matter what. Well, I guess not that cold calling itself works or not. More like, is this sales org particularly good or bad at this skill or somewhere in between?

1:10:31And where can we, you know, just like improving the win rate, where is there some opportunity for improvement? Yeah. I mean, you can sort of blend the listening, the live listening or recordings and just getting a sense for like how the calls are going with the metrics. Some of the metrics would be like if you're making a ton of calls and the average length of the call is like four or five seconds on a connect. So connect equals true, length of call four or five seconds, your intro sucks right off the bat. Like you either sound bad, you sound sketchy, you sound too salesy, whatever. People are hanging up on you before you even proceed.

1:11:13And then you can let that out, right? Like connect is true. Length of call is five to 10 minutes, but conversion rate to a demo set is lower than expected. It means our pitch is we're not finding pain. It's not resonating. And just like following that figure down the line. You know, what's really funny is I come from call centers. Yeah. So one of the first, the first inside sales team I built was for a construction company, $60 million house painting company. I went door to door selling house painting services in college. I remember that. So I became their marketing director. They had no formal marketing department.

1:11:46And they're like, one of the first things they did was like, hey, we're going to start a contact center, a call center. I had no idea what dialers were, never worked inside of an office before. They'd always been outside going door to door and running teams like that. And the call center, these are call center metrics. These are standard things that you look at, like how much talk time are people having? How long do the conversations last? And you sort of compare it across the team. And it's like really obvious where the skill gaps are just by looking at some of the raw data. Yeah. You know, where you can where you can do it.

1:12:16So it's the same to your point. It's the same stuff, man. Yeah, totally. The I mean. Profoundly unprofound, the metrics tell you everything like somebody can just give me access to their HubSpot dashboard and I could put together an entire scope of work for them without ever. talking about and it's just so glaring right yeah so if you're not paying deep attention or you're not investing in the right setup of your systems where you're tracking the right things or if you're not staying on top of your reps to do the hygiene everybody bitches about yeah like you're going to be flying blind and and you're not going to catch that stuff but when you do a good job of it it i mean i don't want to say it's easy but it's clear yeah it's like there's no guesswork 100 we got a couple minutes left yeah um anything else from a pipe gen standpoint that you see working including like in-person drop-bys and you know stuff like that like anything else that you're seeing working outside a good old fashion let's get the list hammer the phones that kind of stuff yeah i think there's always a place for the road show as i call it um i don't know if i want to spend a ton of time on it i think it's helpful but i don't think it's your, I don't think it's your sales machine.

1:13:29Um, I guess one thing I'll just note since it comes to mind is like parallel dialers are super in right now. Um, and I think that they can be really helpful, especially if you're a horizontal company and you have a huge TAM and it's just like, man, there's a billion fish in the sea, just keep fishing type of thing. But, um, another, again, And old school grounding I have here is like I have a lot of companies that are using parallel dialers with a TAM of 10 ,000 total accounts. You're ripping through your TAM way too fast with a parallel dialer. I think I actually my opinion is do it do it first.

1:14:12Yeah. Rip through it. But just know that it's a first pass. Yeah. Like go and shake the hell out of that tree with the parallel dialer and see who falls out. Right. Yeah. But again, going back, going back to what I said before, like, I think people don't realize that there's a, there's an end to that where you actually need to start going much deeper on the accounts and be calling four or five contacts under each account and working the business line and talking to a gatekeeper. And I think a lot of people have an opinion of either it doesn't work or that's just a waste of time and not only does it work but it is just it is the job yeah it just is the job you just have to accept that um so that would be my words of wisdom on that front love man this has been great let's i got two rapid fire questions for you okay hit me okay and then we're gonna take off um first one is just because leadership or any realist sales role can be pretty stressful i'm curious like for you personally how do you like to decompress after tough day tough week stuff like that oh man um my guilty pleasure is call of duty yeah i'll play like two or three matches at the end of the night and that just like somehow just like releases so much so much let's go uh so that's like the more aggressive form of that um i work out my wife and i do yoga sessions in the garage that's we have a little garage gym so that's super helpful and then you know i have a three-month-old if you never held a baby that there's some kind of therapy and that brings you down yeah my last question for you is knowing what you know now what advice would you give your first first time sales leader self man this is more i think more than a rapid fire question um

1:16:10i think my advice is nobody knows what the hell they're doing even the people you think know what they're doing so like be confident when you actually dig in and again run the numbers or form your own opinion do your own diligence diligence uh trust trust yourself on that because a lot of times we kind of just take what we're given, assume it's true, assume it's right. And it just isn't. Yeah. Most of the time. Love that, man. Yeah. Dude, it's good having you on the show. Yeah. Thanks for having me back. So where can people go to connect with you? Learn more about what you're up to. Where do you want to send people?

1:16:52Yeah. You can find me on LinkedIn, Ryan Heafy. Man, I'm not super active on LinkedIn these days. I check it like I'm on every day, but I don't post a lot. You're in operator mode just getting shit done right now, man. Yeah, I'm just doing the damn work, and I love it. I'm having a blast doing it. But, yeah, super easily reachable if anybody ever wants to chat. Bounce an idea off of me. Bounce a roll off of me. Like, happy to do it.

From the publisher

In this episode, Jason and Ryan Heaphy from Fractal Software, talk about what it takes to build a repeatable sales motion in early-stage vertical SaaS. They dig into why the VP of Sales hire usually flops, what a world-class sales playbook actually includes, reverse-engineering quota from pipeline, and what cold calling looks like in vertical SaaS.

Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

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