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30 Minutes to President's Club | No-Nonsense Sales

1 Oct 2026 · 31m · 15 chapters

Episode artwork

#613: Master Parallel Selling Strategies to Speed Up Every Deal | Sam Mckenna | 30MPC Hall of Fame

In short

Parallel selling to speed enterprise deals—how to handle board presentations, start procurement/legal work early, multi-thread across teams, and accelerate vendor review so MSAs get signed faster.

Guest backgrounds

Sam McKenna, CEO of hashtag SamSales; recruited by LinkedIn for LinkedIn Sales Navigator expertise; built a multimillion-dollar business from scratch; claims 13 national sales records; teaches social selling course with 30MPC.

Key claims

Cold outbound is ineffective; use relationship data and network-to-network warm intros. In deals where buyers must go to a board, determine whether they’ll present, ask permission, or tell. Don’t wait for board approval to start procurement/legal—schedule meetings and prepare standard MSA redlines. Identify who “they” are (buying committee, competition, influencing groups). Parallelize vendor review and cross-functional next steps (CS/AM/legal/security) with recurring meetings.

Notable examples

CFO/COO presenting options to law firm partners; Teva Pharmaceuticals deal nearly blocked by an obscure procurement “stamp.” Bad habit: sending calendar links in outbound emails.

Written by AI. May contain mistakes.

Chapters

1:25

Introduction to Parallel Selling Strategies

Discussion on parallel selling strategies and their importance in moving deals forward.

“Today's episode is one of my favorites with her.”
2:20

Understanding Buyer Dynamics

Exploring buyer behaviors and the significance of understanding their presentation roles.

“We start every single episode with your top three actionable takeaways.”
3:16

Engaging with Procurement

Strategies for engaging procurement teams while waiting for board approvals.

“Are there questions that usually come up?”
5:15

Identifying Key Stakeholders

Strategies for identifying and engaging key stakeholders in the buying process.

“Now the grammatically incorrect sentence makes a lot of sense.”
6:54

Addressing Buyer Concerns

Techniques for addressing buyer hesitations and preparing them for presentations.

“When someone's like, I'm going to the board, how do you suss out if they're presenting, asking, or telling?”
8:20

Preparing for Presentations

Advice on how to help buyers prepare for their presentations to stakeholders.

“Could you give an example of a deal or maybe a story where you sense some hesitation in their response?”
11:16

Navigating Complex Buying Processes

Guidance on navigating complex buying processes and engaging with key decision-makers.

“But at the end of the day, you're trying to make them look better by being prepared as they can be.”
14:01

Engaging Key Stakeholders in Sales

Learn strategies for identifying and engaging the right decision-makers in sales conversations.

“Ask these very specific questions that you know a buyer like Nick would care about and that Nick probably would be the only one to answer.”
16:51

Navigating Budget Conversations

Discover how to address budget objections effectively and explore creative funding solutions.

“How should I be running those initial conversations or two with the manager level folks in these deals?”
19:33

The Importance of Multi-Threading

Understand how to effectively multi-thread conversations to speed up the sales process.

“how to sponsor something, 30 Minutes to President's Club, as a great way to attract new talent.”
Show all 15 chapters
23:13

Parallel Processing in Sales

Learn techniques for parallel processing vendor reviews to streamline sales cycles.

“And so talk to me, when is the right time for me to start parallel processing vendor review?”
27:50

Cross-Functional Collaboration

Realize the value of collaborating with internal teams to identify and resolve deal barriers.

“So depending on how you're moving through the organization, if you just got promoted, let's say from SMB to commercial, commercial enterprise, you might've never heard of something called an infosec review, right?”
28:00

Sales Tips and Final Thoughts

Learn about effective sales habits and common pitfalls to avoid.

“That might be the very first time you're hearing an acronym like that.”
28:22

Avoiding Calendar Links

Discover why sending calendar links can harm your sales efforts.

“So we got to move to the final question.”
29:18

Two-by-Two Recap of Sales Strategies

Get a summary of key strategies to enhance sales processes.

“Number two is set next steps in parallel, not sequentially.”
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Transcript

Automatic transcript. May contain errors.

0:00Sellers, cold outbound sucks for both you and your prospect. It takes an insane amount of effort, reply rates are in the tank, and you are fishing in the same pond as everybody else. I literally wrote a book on cold calling, but Sam McKenna, who's the CEO of hashtag SamSales, completely changed my mind about what I thought social selling and great outbound prospecting is. Sam literally has broken 13 national sales records. She was recruited by LinkedIn because she was so good at LinkedIn Sales Navigator and she built her business from scratch into a multimillion dollar business using exactly what she teaches in her social selling course that she built in partnership with 30MPC.

0:43Go to 30MPC.com forward slash Sam. Her new course teaches you how to use relationship data and your network's network to get warm introductions into your dream accounts that would never answer your cold call, respond to your cold email, or open the gift that you sent to their office. If you go to 30MPC.com forward slash Sam, we are giving away all of Sam's favorite LinkedIn sales nav reports, alerts, and scripts that you can use to break into more accounts with less effort. Over the next four weeks, everything 30MPC is dropping is going to be focused on either social selling or one of our best ever Sam McKenna episodes.

1:20And the reason for that is at the end of the month, we are launching our social selling course with Sam. Today's episode is one of my favorites with her. We talk about parallel selling strategies to move your deals faster and create momentum in them. I hope you enjoyed the episode. If you want to pre-order Sam's course, you can do that in the show notes. Enjoy the episode.

1:44Good morning, everybody, and welcome to this episode of 30 Minutes to President's Club. My name is Armand Farouk, and I'm here with my co-host, Nick Segelsky. And today, we have a round two with the one and only founder of Sam Sales. It's Sam McKenna. Nick, why should people listen? So Sam has some phenomenal stuff around parallel processing, next steps in deals, how you should be thinking about getting to power and involving multiple parties, both very early in the deal, but also late stage to accelerate the vendor review process so you are not stuck trying to get a contract signed on New Year's Eve.

2:17This was a very good one, Armand. Three, two, one, let's roll. All right, Sam, welcome to the show. We start every single episode with your top three actionable takeaways. So let's get your three. All right, thanks, Nick. Thanks for having me. Let's talk about first, are they presenting, asking, or telling? Who are we talking about? This is something we're talking about when we're specifically talking to a buyer that says, hey, we're going to go in front of a board and we're going to talk about your deal, right? So we can't get your deal done until we present to the board. That's going to happen in a couple of months.

2:44We'll let you know after that happens. Most people say, okay, that's great. You know, nothing I can do until then. That's it. But here's the thing. You've got to think about what is actually going to happen when that person goes in front of the board. So one of the uncomfortable questions you have to think about when you're asking your buyer about this deal is number one, are you going to be presenting, telling, or asking the board for permission? Are they presenting and waiting for feedback? Are they asking for permission to spend money with you? Or are they saying, hey, this is what we're going to do.

3:11That's a key differentiator in thinking about how your deal is going to move forward. And then on top of that, really quick, has this person presented a deal of this kind to the board before? Is there pushback? Are there questions that usually come up? Is there something that you can help them prepare for? Because if this is the first time they're doing it and they're presenting, not asking or telling, you're going to be in for a different story for your deal than you probably thought. What's number two? Number two, thinking about parallel processing with procurement. So let's say for the same deal, person comes back to you and says, there's nothing we can do.

3:45I don't know. Let's say it's August and we can't do anything until this presentation happens in December. Great. Let's start talking to procurement. Can we get in front of procurement and get our MSA done? Can we go and do red lines? Can we understand how they buy, what the processes are, what stamps we need, what buying thresholds happen? Can we do all of that? And the buyer says, we could, except we don't have approval yet to move forward. We won't have until the board meeting happens. and because procurement is outsourced, we can't do anything with them until we have these levels of approval internally.

4:14So again, most reps would say nothing we can do. We can't touch procurement until then. So two things I would tell you to do here. Number one, make sure you have the meeting scheduled with procurement directly after that presentation happens, right? There's absolutely no harm in getting the meeting scheduled. Not only will this help you make sure that you get on their calendar now before everybody else is trying to do it, but to make sure that you get on your own legal and procurement teams calendar right now, again, before everybody is rushing. The second thing, ask for a standard MSA. You've done this before buyer, presumably, right?

4:48So what are non-negotiables? What do you guys never agree to? Do you have net 45 terms, net 60, net 90? Do you only do litigation in Delaware, Texas, California? What does that look like? Because here's the thing, whatever they want, we're not going to ultimately agree to. We're going to have to go through our own legal procurement, rev ops, sales ops to get certain things done. So do that all in advance and have all that documentation ready and the meeting scheduled way before you ever need to. Round us out, Sam. What's number three? All right. Let's think about who are the they's. Now the grammatically incorrect sentence makes a lot of sense.

5:23So I want you to think about whether you are a leader or whether you are a rep, every single time you hear the word they from your rep or from your buyer, we want you to ask yourself, do you know who is in that they? Is it they, the competition you have? Is it they, the buying circle? Is it they, the influencing committee? Who are the theys? Because I think about every time I've heard that from a buyer and the buyer says, Hey, we're going to look at this proposal. They're going to take it back to the team. And then they're all going to decide together. And I said, that sounds great. Thanks. What I really need to say is that's awesome.

5:55Do you know who's in that buying committee? Who makes up those days? And I ask, because I wonder if part of those are people who have been our clients before, if they have mutual connection with our executive team, if they've worked with our CS team before, right? If you buyer are serious about working with us, tell us who those days are because man, we'll be able to figure out who they know, what experience they have and help this deal move along. Same thing on the competition, right? When we hear they about the competition, they're submitting their proposal. They are going to answer the questions that we have buying COB Friday.

6:26Who are those days? We have to find that out because if we don't know who the competition is, we're aiming in the dark. Imagine if we're selling, I don't know, a$250 ,000 car and they say, we're going to look at the competition. We don't know who that is. And then we later find out, I don't know, it's a Prius and maybe a 1989 Honda. Great cars, maybe not good competitors for our quarter of a million dollar car. Figure out who those days are. You'll open up a whole series of information that you need to know to get your deal done. Sam, that first takeaway is amazing. When someone's like, I'm going to the board, how do you suss out if they're presenting, asking, or telling?

7:01I think what you need to think about is change the lens of how you look at this partnership with your buyer. We are so uncomfortable in asking uncomfortable questions because we don't want to upset anybody. We don't want to step on toes. If you inset about, think instead that it's you versus them, think it's you too in cahoots, right? They want your software solution technology, whatever it is, as much as you want, let's be honest, their money and the revenue, right? When you go into this board meeting, when is this the first time you've done this? And two, are you presenting? Do you have to ask for permission?

7:32Are you telling them like, because you have authority to do this? Tell me about that. Simply by asking this, right? You're hopefully going to open up the conversation for them to be honest with you, tell you exactly what's going on. And for you to think about those questions that are forthcoming, those objections that they're going to get, you can build an analyst for them. You are going to make sure that they are prepared as all get out for this presentation or hopefully this. Now, if you think about that advice and you're like, oh, that makes me cringe, that may also be a sign that one, you don't feel like this deal has as many legs as it does or two, that you haven't built the relationship enough with this buyer, what we talk about all the time, understand your buyer, who they are, not only as a wallet shareholder with somebody with wallet share, but also who they are as a human being.

8:16Get to know them, build that rapport, and then you can earn the right to ask those questions. Could you give an example of a deal or maybe a story where you sense some hesitation in their response? This is something that happens when we listen to discovery calls and we listen to calls that move further along all the time. We hear the hesitation because the rep is really just pushing and pushing a particular solution that hasn't been vetted correctly. So maybe that buyer just says, you know, we're making our presentation of the options on December 12th. The person hears, you know, happy ears. They think that this is going to move forward.

8:48They throw it and commit. But we hear the hesitation there from the buyer to give any additional information because they're probably not sure that that's the opportunity that they're going to go with or the solution they're going to go with. Again, this is why just in the very beginning, the discovery work that you do, asking open-ended questions, broad questions about the true business pain they have is so critical. So we can really understand who we're dealing with and if this opportunity is worth our time. Sam, let's make this real. I sold accounting software to law firms for a very long time.

9:20And very often the CFO or the COO of the law firm that was looking at our solution would be making a presentation at the quarterly meeting of all of the partners of the law firm. I'm in that conversation with CFO and they're like, hey, on December 12th, we're going to be giving a presentation to the partners of all the options. They tell me we're going to be presenting options. What should I be asking them? And what are some of the other questions I should be asking them to help them have a better presentation and help sway the deal in my favor? The first thing I would do, especially because you sold accounting software to law firms, right?

9:55And you understood the law firm and the professional services space, which is one that I specialized in for a very long time. The first thing you should do is make sure that they understand your expertise in their space. So you could leverage that to earn the right to ask these questions. So number one, to say, you know, the last time I worked with K &L Gates, So last time I worked with Scadden, right? One of the things that came up was partners always seem to ask this. The managing partners or the buying committee, right? The executive committee asked this and this and this. Have you guys heard those questions before?

10:25Is that important to your firm? Tell me about that. The second thing that often comes up, and I know every firm is different, but when we think about this, is this all within your authority or is this something that needs a majority vote in terms of spend volume, right? What does it look like for you guys? right? Is this ultimately your decision or do we need to get some buy-in? The other thing to think about is how can I help you prepare for that meeting? As you guys have presented, you know, software that you want to purchase before, what questions come up? What objections come up? I know sometimes firms have one or two very persnickety and skeptical partners.

11:02Do you guys have that in your group? And how can I prepare you for their questions to make you look like a star? Use it in a language that feels authentic, not only to you, but then also that fits the personality of that person. But again, you are helping your deal get across the line. But at the end of the day, you're trying to make them look better by being prepared as they can be. So there's also going to be some scenarios where somebody goes, hey, I'm not going to be presenting. I'm not taking these options back on December 12th. I'm going to be telling them this is my recommendation for us moving forward.

11:31How does the conversation differ there with your champion? I think you ask them the same question that you're a leader or that you should be asking yourself. Why won't this deal get done? What's your perspective right after you say we're going to buy the software, it's a multi-year deal and we're going to buy it for 5 million bucks over the course of three years. Why do you think that won't get done? Any objections that you can anticipate, any pushback you can anticipate? Are there relationships maybe that others have with particular software firms that we need to think about? what can I do to prepare you for this?

12:03Maybe knowing what you've known from presenting options like this before. The other thing I would focus on, again, is thinking about the procurement process for whatever spend volume you're getting at. Some people don't think that this is something that they have to go through depending on the size of the organization and the price of the software. But let's say even if you are presenting to a multi-billion dollar organization of Fortune 500. Oftentimes it's the opposite of what you'd expect. Procurement's tougher, spend thresholds are lower, right? And you need 16 different stamps from 14 people who are all going to be on PTO at varying times to get your deals done.

12:39So ask those questions as best as you can. I thought one of the other things that Sam does really, really nicely there is you're not just asking the, hey, what's Matt going to ask you when you go in the room? You are suggesting for them. Hey, might it be that there's others that have relationships with other software firms that like might sway their opinion on things? You're almost giving them a couple options. Because if you just ask the big high level question of like, what resistance might there be? It's hard for them to do the full search of every possible combination and permutation. But if you say here's some common resistances, they can pick some of those and you can talk about them.

13:15But it also starts to jog their thoughts. I do want to double down on what you just said, Nick, really quick, because I think it's important. This is part of every single part of our sales process is that suggestive capability. If you just said, what are the questions that are going to come up? You're going to get what's already been in their buckets or what's in their minds right now. We lose deals all day long and we know why we lose deals all day long, right? We have that basket of here, the 78 reasons I lost deals this year. So think about those things as they would apply to this vertical, this buyer, the size of deal and suggest that stuff, right?

13:49People say all the time, how do I multi-thread without being salesy? Nick's the ultimate decision maker. I'm talking to Armand. How the hell do I get to Nick without stepping on Armand's toes? Start asking questions that Armand can't answer instead of being like, what's Nick going to care about? Ask these very specific questions that you know a buyer like Nick would care about and that Nick probably would be the only one to answer. What are the priorities for this year? What are you guys forecasting? What's the growth? What's the roadmap? How are you going to get there? Ask these specific things that Armand's going to say, you know what Nick's probably a better person to answer those questions why don't I bring him in and he'd be like that would be super so how do you broach that conversation because every once in a while you're champions of a buffoon and like unfortunately you're selling to a buffoon and it happens and I've sold to a people leader where I'm like I know this head of people has to be the person that's going to talk to the CFO it's they're not a champion they're just a champion that I know has no political clout so I'm asking them all these questions they're like I don't know I don't know.

14:46I don't know. How do I get them to pull me into that meeting instead of taking it alone? One of the things that I think is really cool about sales is that you can use language to your advantage. We talk about this all the time, hashtag semantics matter. So one of the things I love to do there is to say, why don't we do this? Armand, I probably filled your head with all these questions and you're probably frustrated with how often you're saying, I don't know. Do you think Nick would have a better sense of these answers? It could be Lukeman. Or I also wonder if your SDR leader would have some great, you know, things to share about their frustrations, kind of what they want to do differently.

15:20Why don't we do this? When don't we grab another time to chat? I've got a couple of things I want to mention. I said, I'm going to actually include our CS leader who I think will have some really great perspectives on this. And then why don't we grab Nick and, you know, buffoon number two over on your SDR side to come over on our call. How does that sound to you? This will also give you a good temperature check. Are you talking to somebody that's just going to buffoon your buns off, right? and be a gatekeeper the entire time? Or do they actually have authority to help make decisions here, to bring in multi-threads, right?

15:49And to move it forward. Because we have talked to those people. And if you talk to just that person again, and you don't figure out how to multi-thread, you are going to do nothing but waste your time. So come hell or high water, why don't we do this and suggest the other people to bring in? Can we go to the suggestion that you made, which was asking our buyers questions that they don't know the answer to. This is something that I've struggled with in my career. I sell all of our sponsorships for 30 Minutes to President's Club. And usually we need someone who's at least a VP level, maybe even a CMO to approve our level of spend.

16:29Usually our deals start with a marketing manager. And that person wants to collect a lot of information from us. They wanna know about our audience and our demographics and our pricing and the activations. And nine times out of 10, when I give them all of that information, they take it back to their boss. And I have a closed loss deal that Armand is yelling at me about and saying, go back and go higher. But foods can sell too. Who would have known? How should I be running those initial conversations or two with the manager level folks in these deals? I think help educate them on the objections that you're already going to get.

17:04So let's say, right, the objection, what's the most common objection that you got? sometimes we get, we don't have budget for this. Our budget's already, you know, allocated to whatever. Now I would argue, right. A lot of the time that from a budget perspective, it's just because we didn't prove value. So let's say we get on, you know, with a marketing manager and we say, I'm going to run you through our demographics and things like that. I want to ask you just a couple of quick questions. So one, mostly around budget, right? Sometimes we get pushback from our buyers who say, oh, we don't have budget allocated for this.

17:33And we have to get creative with them about where to pull budget from. When you think about your sponsorships or even thinking about all the different buckets where your marketing dollars go, what's your sense on what's been the most successful, what hasn't had great ROI? Tell me a little bit about that. Oh, well, I really only see sponsors, oversee sponsorships. Tell me who does your syndicated third-party content. Tell me who does your pay-per-click campaigns. Can you talk to me about that? Should we bring them on the call? Because I think, right, one of the great conversations we can have when we work with your broader team is thinking about the places where ROI just isn't clicking and pull budget from those places to help you get sponsorship of our podcast.

18:09Any thoughts there? Just start to think about those questions, right? If you want to work with us, we got to get creative. I think it's so smart what you're doing is you are raising that roadblock and you're not afraid to have that uncomfortable conversation of like, hey, usually this is an area that and you're saying this really, really early, maybe even before you've proven all the value of what you do. you're saying we're probably going to have to get creative and we might need to pull from some of these other areas. And I feel like you're also helping them expand their scope in their mind of like who actually gets impacted by something like this.

18:42You mentioned the folks running the paid ads, the folks doing syndicated third party content, which isn't normally folks typically have a far more narrow lens in terms of how they're thinking about whether it's a sponsorship, an accounting software, or whatever people are buying. What you have to think about all the time is that people are coming to calls with you, not for their health. There's an actual challenge that they have to solve. There's something they're looking to accomplish. So what is that? What's the budget that you have available for it? What are other budgets that we can pull from?

19:10And I think just an important takeaway, especially even for our senior sellers, the amount of times that we hear back again, budget was a concern or budget wasn't allocated for this. Well, no shit budget wasn't allocated for this, especially if it's something new that you're selling, but you have to figure out how to partner and multi-thread to pull from different budgets. And it may not even be what you think. Perhaps, right, you're thinking about how to sponsor something, 30 Minutes to President's Club, as a great way to attract new talent. Can we talk to HR? Can we talk to your chief people officer?

19:41What are you guys doing to bring in fresh young minds? Because I'll tell you, our demographic maybe is 6 % BP, but the BDRs that are really investing in themselves, the AEs to better themselves, they're listening to our podcast. So think about that, right? What are creative places where you can get money? I was running into this issue the other day where a founder was about to multi-thread. So they were about to go from champion up to power and they actually got to power on the second call. And the problem was the champion wasn't convinced yet. So literally the champion was, they still had both vendors in their head, two or three vendors in their head.

20:18They were like, this one's more expensive. This one's less expensive, whatever it is. and what he actually ended up doing is for future deals who were like let's delay multi-threading up until we can at least say that we have one or two people bought on board and so i want to get your reaction on that at times does it make sense to slow down that presentation of power to get your ducks in a row or do you want to get in front of power as soon as possible i would always start with power if you can so maybe just a quick caveat there right don't be afraid to go up the food chain. And again, one of the things we talk about with our show me, you know me methodology is that you have to basically put in the effort to do research, write a great subject line.

20:57People are like, well, who does that skill to 400 marketing managers? It doesn't. You just go to the CMO and you say, here's what we can do for you and then work your way down. The part just by the way that I love about that is if I, let's say Nick is the CMO, right? And I go to Nick and he says, go to Armand. Now when Armand either blocks me, doesn't respond to me or whatever, not only can I go back to Nick, but I can also just keep Nick abreast of what's going on because Nick introduced me to Armand. So go up first and then work your way down. The part I love about sales is that it's an art, right?

21:28It takes your EQ and account. It takes you really understanding the dynamic of relationships and people to get ahead. So take each opportunity that you have in a different way. I would just say, like, think about what that person's like, what you need to do. If they are skeptical of you, if they already have relationships with other vendors, you've got to really suss that out. But more than anything, show up to the call to solve a challenge. So don't come and say, tell me about the landscape that you guys have going on over there. Tell me about your challenges. Tell me about the issues you're trying to solve.

22:00What are the initiatives you have ahead? I'd love to hear about you guys first. Let them data dump on you and really look to solve their challenges. Because if you make that investment in them, like no other reps do truly, they're going to take you to power pretty quickly, hopefully if they're the right buyer to begin with, but start there and then feel it out. I say more often than not, faster that you can multithread and get to power, the better. Even if it's not power, multithread double the quantity of the people you have on the call. Get two marketing managers on the next call instead of just one.

22:30It doesn't always have to be up. Yeah. The way that I think about it as well is you might have to multithread less before you multithread up. And to me, that's the more conservative path, but you shouldn't just stick with someone who's not convinced for 20 steps and wait for them to be convinced. That might mean you don't send them to the board on day one, but you should actually still go and try to get some other allies in your deal cycle. The last to go back to is actually your second takeaway, which is all of this has been talking about getting to power, getting approval. And there's another step that can slow down the deal that happens after this, which is a three-month vendor review with procurement and legal and security.

23:12And everyone knows, or many people know that the best reps are parallel processing vendor review during the evaluation. And so talk to me, when is the right time for me to start parallel processing vendor review? I think again, as soon as you have what you need to know that this deal is going to move forward. So whether you subscribe to Bant and you've got all that figured out, whether the buyer has said, we are moving forward with you, I am telling the board what I am doing and it is going to happen on December 12, whatever it is for you to need to know and for your leaders to know that this is a 90 % commit deal, 75 % commit deal, whatever it is.

23:46Once you get there, you've got to think about how do you speed up that process, right? Because by the time, if you're parallel processing this paperwork, by the time the decision happens, by the time the person comes back from vacation, that's going to sign your MSA, whatever that is, you're going to have 95 % of the paperwork done. I also just think about the personal pride that I have as a seller of being able to go to my leader and say, here's what we need to do. It's August, deal's not going to happen until December, but I've gotten this checked off. I've gotten our MSA's red line. I've gotten 17 people on our side to approve the nine things that are not going to be doable on their end.

24:22I am as locked and loaded as I possibly can be. And then I'm still working with my leader to say, why won't this deal happen? What else haven't I thought of, right? The last deal I needed to get to my first president's club was with Teva Pharmaceuticals. And it's when I learned that there was a stamp that was needed by some obscure procurement team. And I didn't know this, right? I mean, this was going to cost me my first president's club. So even making sure, talk with your peers, talk with cross-functional leaders. If your leader is a buffoon, talk with other leaders and say, what am I not thinking of?

24:56Right. Also, the importance of sponsorship internally and mentorship internally. Go and meet with a top performer. What haven't I thought of? Make sure you figure that stuff out so you can be thinking about all the stuff right before you get to that end goal where you instead of going back and be like, crap, I wish I thought to do that, you know, put in the work. Other than late stage vendor review, let's actually go backwards to earlier in the deal. What are some common places that you recommend sellers have parallel next steps rather than sequential next steps? I think one really great thing is to think about the other cross-functional teams that you'll be working with.

25:33So even as you think about, you know, we're going to move this up the ladder, we're going to talk to our leaders about it and get that approved. Let's say we're talking about a multi-year deal. And we know that as soon as we sign, our CS team is going to kick in or our AM team is going to kick in. Are you also multi-threading across those teams? Have you brought in your CS, your AM team? Have you brought in an AM manager? Have you brought in your executive leader to get a meeting with that executive leader, let's say on the other side? These are all things that you can do to start them multi-threading, but also to build those relationships.

26:05I think the other thing, just as we're waiting on other next steps and people really miss this for enterprise deals is to make sure that we have recurring meetings happening. So again, if we're in August, let's say, and we're still forecasting this for year end, December. What I want you to think about is how much work and continued poking and prodding needs to happen to get that deal done. So do you have a meeting with legal and procurement on your teams every week, every other week? So that we're holding ourselves accountable to, these are all things you can be doing again, to keep that deal moving and to keep the relationships building in parallel.

26:37I love how you're pulling so many of these plates earlier, the cross-functional aspects, the procurement aspects, the legal aspects. And folks, oftentimes I have the exact same rule, Sam, which is I start trying to parallel process the moment I feel like we're selling on the same side. So the moment I'm like, okay, we're on the same side of the table and it's not, I'm trying to win you over anymore. It's like, all right, that's when we start parallel processing. But sometimes that happens later than you want. And so there are still things you can do early in your deal cycle to sort of get sneaky and start vendor review.

27:09For example, you can get an NDA signed early in your deal cycle, and that will usually at least get you on the radar of legal. Oftentimes what we would do is we would like spin up a trial portal or we would spin up a demo instance for someone. And that oftentimes kicks off a lightweight security review. And it just like gets the IT review started earlier than you would need to. So get creative and figure out all these ways that once you get good at closing deals, if you're good at closing a deal in four months, your next task is not to just figure out how to close all those deals and close more of those deals.

27:40It's figuring out how to close your four month deals in two months. And that's where the best sellers actually make it to club. I think you just said something else. I think that also might perk up some ears security review, right? So depending on how you're moving through the organization, if you just got promoted, let's say from SMB to commercial, commercial enterprise, you might've never heard of something called an infosec review, right? Or security review. That might be the very first time you're hearing an acronym like that. So again, I think the importance of working with cross-functional partners internally, why won't this deal get done?

28:09If you went to Armand and he was like, well, did you do infosec yet? And you said, what is that? Just easy ways for you to learn and be proactive about the way you chase this. Wow. Sam, we're going to need to have you back. This was one of the best ones in a long time. And sadly, we are running out of time. So we got to move to the final question. Final question is this. We've talked about a lot of really great things salespeople should be doing. Now I got to ask you about a shouldn't. And so the last question is, what is one bad habit that you see a lot of salespeople exhibiting that you think they need to break because it hurts them more than it helps?

28:40sending calendar links in your outbound emails. Dear God, don't do it. Two quick things on this. Number one, if you send a calendar link, it is presumptuous. Number two, you're putting the onus on the buyer to schedule time with you. If you really, really want to be selfish in the way to think about this, as you object and say, but it's so convenient, Sam. Here's what you want to think about. Instead, you are letting a buyer circumvent all of your personal stuff on your calendar, your one-on-ones, your daily massage, trust me, all the things that you have to do. You're making them circumvent that instead of saying, you tell me when you're free and I will make that time work some way come hell or high water.

29:16Don't do it. All right, Nick, it's time for a two-by-two recap email from this episode with Sam McKenna. What do you have for your two? The first is the recurring meeting. You will eventually in complex deals get to a stage where you and your champion are selling together and you are probably going to need to meet with them on a regular basis to get intro to multiple different parties, to cover different questions and items on their list. Number two is set next steps in parallel, not sequentially. You do not need to just have one next step on the book if the next next steps are not contingent upon that next step.

29:53The example Sam shared was if you have next steps with different cross-functional groups, customer success, the technical team, the attorneys at the law firm that you're selling to. If those aren't dependent upon each other, get them all scheduled now because now you start to create some momentum in your deal and everything moves faster. Number three, you need to figure out if your prospect is going to present to the board, ask the board, or tell the board they're buying this thing. And if someone is presenting to the board, then that means you have a lot of work to do with your champion and you need to unpack their concerns and prepare them for the questions they're going to get from their financiers.

30:34Number four, if you want to get access to power, you can start asking your champion the questions that they don't know the answer to. All of the things that a CFO or a board member is going to bring up, prompt those to your champion. And when they don't know the answer to them, you're like, hey, is this something that Nick might know the answer to? And that's your in. Today's show is brought to you by Proposify, the proposal management software designed to make every deal a closed deal. When you send a proposal to a prospect, include a video of yourself walking through the proposal because it's going to be shared with stakeholders beyond just your champion.

31:07You want to make it easy for those other people to digest and you want to be able to control the narrative with your presentation. And bonus, Proposify data shows that when buyers watch the video, it increases your chances of winning by over 3x. So do not let your proposals become a disappointing plot twist. Get our proposal success guide free in the show notes. If you are sick of non-actionable takes about AI and sales, you might be interested in attending my live session at Apollo next on September 30th in San Francisco. Come and join if you want to join actionable sessions with teams like yours, if you want first looks at Apollo's biggest launches, and if you want to network with operators who are talking action, not academia.

31:43I promise that you are going to walk away with stuff that you can put into action right away, and you can register for free if you use our 30 NPC link or code in the show notes. I will see you there.

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Samantha McKenna, CEO of #samsales consulting, joins Nick and Armand to share strategies to get to power through multithreading and speed up deal cycles with parallel selling

ACTIONABLE TAKEAWAYS:

Schedule regular meetings with your champion to maintain deal momentum and reduce scheduling friction.

Schedule multiple next steps simultaneously if they're not dependent on each other to accelerate the deal.

Determine whether the prospect will present, ask, or inform the board about the purchase, and prepare accordingly.

Ask your champion questions that they might not know, prompting them to involve higher-ups who can provide answers.

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