2294 - How Documented Processes Improve Onboarding and Performance with Sales Performance Team's Nicholas Loise

21 Oct 2025 · 18 min

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Podcast Episode Summary: The Thoughtful Entrepreneur - Episode 2294

Episode Overview Title: 2294 - How Documented Processes Improve Onboarding and Performance Host: Josh Elledge Guest: Nicholas Loise, Founder of Sales Performance Team Duration: 15-25 minutes

This episode highlights the challenges and strategies involved in transitioning from founder-led sales to building a high-performing sales team in small to midsize businesses (SMBs). Nicholas Loise shares insights on creating scalable sales systems, the importance of documentation, effective onboarding processes, and maintaining team performance.

---

Key Concepts Discussed

  1. Challenges of Founder-Led Sales
  2. Founders often become the bottleneck in sales processes.
  3. Hiring salespeople can be daunting due to the differences between small business dynamics and large enterprise environments.
  4. Sales success in SMBs relies heavily on creativity, adaptability, and a strong sales process.
  1. Documenting the Sales Process
  2. Importance: Documenting every step of the sales process, from prospecting to closing, creates a clear roadmap for new hires.
  3. Founders should adopt a "beginner's mind" when creating these documents to ensure nothing is skipped.
  1. Hiring Strategies
  2. Recommendation: Hire two salespeople simultaneously to foster collaboration and reduce hiring risk.
  3. This approach allows for performance benchmarking and supports morale.
  1. Onboarding Best Practices
  2. Invest in structured onboarding during the first 90 days to ensure rapid ramp-up and employee retention.
  3. Create milestones and shadowing opportunities to enhance the onboarding experience.
  1. Compensation Structures
  2. Compensation should be clear and motivational, typically consisting of a base salary plus commission.
  3. Transparency in compensation encourages results while providing stability for new hires.
  1. Performance Oversight
  2. Maintaining oversight without micromanaging is crucial.
  3. Regular reviews, feedback loops, and playbook updates help ensure ongoing team success.
  1. Cultural Fit and Assessment
  2. Use objective assessment tools to evaluate candidates for their fit within the company culture and their potential performance under pressure.

---

About Nicholas Loise

  • Founder of Sales Performance Team.
  • Expert in building scalable and high-performing sales teams for SMBs, specializing in sales playbooks, recruitment, and onboarding.

About Sales Performance Team

  • Focus: Assists companies with sales revenues between $1M and $25M in transitioning from founder-led selling to a structured sales organization.
  • Services include fractional sales leadership, team recruitment, and compensation design.

---

Key Episode Highlights

  • Founders often underestimate the challenges of hiring sales reps for small businesses.
  • Documenting the sales process is crucial for successful onboarding and training.
  • Strong onboarding processes significantly impact long-term sales performance.
  • Keeping compensation plans simple and transparent is vital for attracting and retaining top talent.
  • Regular assessment and feedback are important for maintaining team performance.

---

Links Mentioned

  • [Sales Performance Team Website](https://salesperformance.team)
  • [Nicholas Loise LinkedIn Profile](https://www.linkedin.com/in/nicholasloise/)

---

Conclusion This episode provides valuable insights for entrepreneurs looking to scale their sales operations while maintaining quality and effectiveness. By focusing on structured processes, thoughtful hiring, and effective onboarding, business leaders can build self-sustaining sales teams that thrive beyond the founder's direct involvement.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:04Well, hey, Thoughtful Leader. Welcome to the Thoughtful Entrepreneur. On this show, I interview purpose-driven founders, experts, and change makers who are making a real impact in the world. Want to be a guest? Simple. Go to upmyinfluence.com and click podcast. I'd love to promote your story to our audience of over 100 ,000 and across over 2 ,300 daily episodes and counting. Want to get booked on other great shows like this? Simple. Go to podverified.com and get your free guest authority score. Thousands of hosts are looking for high quality guests and Podverified connects you the right way. Now let's dive into today's episode.

0:58With us right now, it's Nick Luisi. Nick, Nick, you are the founder of Your Sales Recruiter and Sales Performance Team. You're found on the web at salesperformanceteam.com. Nick, it's great to have you. Oh, it's an honor to be here, Josh. Thank you so much for all you do, and thank you for having me on the show. You live in one of my favorite cities in the United States, that's Chicago. My wife is from Chicago, and you and I were talking before we hit record, and you mentioned we were just talking about the bear a little bit. and that you mentioned that you're about to, or you enjoy Chicago dining.

1:37And I am envious. Tell me where you're going tomorrow. Yeah, so we're going to the next restaurant, which is part of the Alinea Group, right? So one of my superpowers, the things I love to do with my wife is we're foodies. So this is a tasting menu and every year I buy her a subscription to this. And it's three meals with wine pairings and it's focused around one chef. So the first year that they did this, and if you look up Alinea Group or you look up Next Restaurants, you'll see it's the top of tier, right? The only Michelin star, one of the only three Michelin stars in Chicago. First year, it was tasting menus focused around Julia Child, which actually brought my wife to tears, which is an interesting story.

2:22It was so great. Wow. Charlie Trotter and Rick Bayless. this year it is um it what it's massimo uh and i forget his last name but it's the famous italian chef and it's my wife's favorite chef in the whole wide world so we are going to that and then we and then the last one is next and then the last and the first one uh was focused around um you know charlie trotter's restaurant as an homage to him and he's actually opening up charlie trotter's restaurant again because he worked there you know under the toolage and he's going to do it for a very finite period of time. So if you think about, you know, the tragic story about, you know, Charlie Trotter, great chef, phenomenal chef, very, you know, kind of pushed the restaurant experience in Chicago to where it is now, and then died suddenly of a brain aneurysm at his house at a very young age.

3:14So it should be a lot of fun. And we're looking forward to it. And we love going to restaurants, right? So we just came back from North Carolina, hit a number of restaurants was on the coast so we had a lot of really good seafood so French Italian you name it we are are big fans of it and so then that also keeps me in the gym every day right because I have to burn off all of the wine and the and the food and the calories and those wonderful desserts so it's a it's kind of a yin and a yang well I was just looking at next websites and they said on any given night there can be 10 ,000 plus guests on our wait list season ticket holders get priority at all Alinea group locations if there becomes an availability.

3:55That's just crazy. If you're in customer service, I mean, they do a phenomenal job. So whenever we have people come in town, you know, we try to take them to maybe one of their bars, right? So they do those really high-end experienced bars where, you know, like every drink has a theme and a story. So that's a lot of fun for out-of-town guests too. So, you know, it's a great experience. No, no doubt. Okay. Go ahead. Yeah, well, Nick, we need to talk about it. Yeah, let's talk about sales, most importantly. I'm like so fascinated by this. And it's certainly like anyone who has been watching the bear, I think, you know, your curiosity can get peaked a bit, you know, just by the culture there.

4:36So tell us, Nick, about the work that you do with your brands, with your sales recruiter and sales performance team. Sure. So the main company is Sales Performance Team. And what we do is we act as our team acts as fractional C, SOs or VP of sales for small to midsize companies. And that's anywhere for a million dollars in sales to about$25 million in sales. They can't afford a full-time, nor should they afford a full-time VP of sales. So they bring our team in as a fractional sales leader. And so we work with all different types of industries. least. Your Sales Recruiter is a company and a brand that we created because we are being asked to do more sales recruitment for our clients, but also for new clients.

5:23And going out as sales performance team just didn't make sense because people didn't understand it when you said, hey, I'm recruiting. And so we created the brand Your Sales Performance Team, and it's really our recruitment arm. And so right now, if you go on our website, we probably have about five to 10 open recruits for various clients that we do. And it's all retained searches, right? So it's not like we're running around there and doing non-retained searches. And a lot of our searches are for clients multiple times. I can imagine that for an SMB, particularly one that's maybe been led by founder-led sales for quite some time, hiring a sales professional or sales director, that can be fraught with peril.

6:05Yeah. And it can be very expensive, right? So it's fraught with peril. Will this person succeed? Will my money be paid back? And many of them have had their heart broken because sometimes they, especially for the sales leader side, but it's a great question, Josh. Sometimes they go out and they hire somebody from a very big corporation or a very big brand or logo thinking that this person is going to knock it out of the park. We actually see this on the sales leader side as well as the salesperson side. And what happens is that person is used to that bureaucracy, that overhead. The salesperson's probably used to that brand of opening the doors and doesn't know really how to be crafty or kind of sell in a small business environment.

6:48And so the sales leader is used to kind of really working with a large organization with a lot of overhead, doesn't know how to be quick and nimble and kind of get things done. And then equally so on the salesperson side, you know, we have clients that are digital marketing space and they're like, you know, I hired a bunch of guys out of Google and they couldn't sell for me. I'm like, well, that's because they're used to the brand of Google opening the door. Nobody sells Google. Everybody buys Google or they come from Salesforce, right? And Salesforce, they're used to that brand and that brand opens the door and has that inherent trust built into it already.

7:24So when you're selling for a small business, maybe their second, third, or fourth choice down the line, you have to be much more craftier in your sales processes. And all of your collateral and marketing has to tell a different story so that the person takes the choice for you. Yeah. Well, Nick, I'm wondering if you could maybe share some tips. Like, let's say that someone's listening and their goal is, let's say they have a small agency and the founder's still way heavily involved in sales, right? And they don't necessarily have the staff to kind of do that. They've thought about, you know, like, oh, how do I step out of this?

8:06You know, I want to give myself some more time freedom so I can kind of do more, you know, CEO level stuff and evangelist work. You know, that's kind of what's in their zone of genius. They're doing sales because they're competent at it. They're good at it. And they're obviously selling a lot on founder magic. if they wanted to hit the goal of being able to transition out, let's say over the next six months or so, like what initial things would you recommend that they get started on? First and foremost, start creating SOPs and create a sales process, right? And so our big thing is creating a proven and repeatable sales process that a C-level salesperson or B-level salesperson can be successful in doing, right?

8:47So think of it as what does it take to sell something down here? Now, the problem with the owner doing this still, Josh, I have to put this level of caution is the owner intuitively knows how to do stuff. So they may skip steps in the process or skip steps in the documentation of the process because of the fact that they just, I can wake them up at three o 'clock in the morning, they could sell their product or service. And so they kind of have to go to a beginner's mind and say, what happens throughout the entire sales process from open to close from this? What does the approach look like? What is the discovery questions that I always ask for?

9:26If they say this from an objection standpoint, what is my rebuttal? If they say this from a question standpoint, what does my rebuttal look like? And so build out your sales process and your sales playbook, and that will help getting C-level players, B-level players up-leveled. And that's really what you want to do from a business owner standpoint. Second thing, if you're going to hire somebody, we always say hire two. One is it gives them a buddy, but it also gives you that person, if one fails, you're not back on taking the sales calls. The third thing is when you're looking at hiring or even looking at the sales process, your onboarding process in your first 90 days sets the tone.

10:05So make sure that that's really buttoned up. Make sure that you really have a really good onboarding process for the salesperson so they don't start looking for that job at 91 days. And now you've wasted all that time, opportunity costs in that. You know, the biggest cost in business is the cost of missed sales. And most organizations don't realize that. So you got to really figure out how do I set up success to capture as many leads as I can, but also capture as many sales as I can. Right. To someone who's not hired a sales professional, what is that world like in terms of, you know, you might think, oh, well, you know, am I going to be doing a compensation?

10:44Am I going to be doing commission with them? Am I doing a hybrid? Am I just doing flat salary? I mean, what's normal today? And again, I'm sure different industries are a little bit different. You know, I'm thinking of, you know, a lot of like your maybe like your agencies, your B2B service providers, you know, that sort of thing. So I think it's a lot of it's different on the sales cycle and your sales ticket, right? And so, yes, today it is based in commission, right? And I know everybody wants to go commission only, but then the salesperson has to have some level of compensation coming in, especially for the first 60 days, 30 days, 90 days.

11:23So it is a combination of base and commission. A lot of it is what is your contribution margin, right, for the products and services that you're selling? And what does that look like? And so what can you afford to pay out as a commission? You know, rule of thumb, we're using anywhere from 5 % to 10%, right? We don't usually give a little bit more than that. Sometimes we front load the commissions, especially on SaaS products for people. So we kind of figure out really what is the business model and kind of build it out from there. Sales owners always kind of fret with this a little bit. I don't know why, but it's just, you know, what can you afford to pay?

11:59What is the average sales cycle? What does that look like? And how soon can you get that salesperson to be net income positive and generating, you know, contribution margin as soon as possible to you? Because it's really all about that, right? So it's not just from the revenue standpoint. And you know this, Josh, as a phenomenal entrepreneur and launching a number of businesses. It's also what is the profit and what's the contribution margin that I want to bring from that? And what do those sales look like? And of course, I think, you know, here where we're going, you know, you bring in some competent sales leadership and trajectory, probably, I mean, it has to be great, you know, because I think, you know, a lot of folks that are kind of stuck in founder led sales, I mean, they're the ones, they're the kink in the hose.

12:45Correct. And some of its control, they don't want to give up control. Some of it is that they've had their heart broken, and they've hired salespeople. They've hired the wrong salespeople. So then they're just, they don't want to do that again. And I realized that, listen, I'm not taking it lightly. And there's a lot of really good at interviewing salespeople out there, but they are horrible at selling in the environment that they're hired to sell in salespeople, right? And so you see a lot of that. They've been at someplace for a year, right? Maybe a year and a month, right? And nine months. And when you're asking them why they are leaving, they won't tell you, but what is because they just didn't produce, Right.

13:22And so you really kind of have to get into that. One of the things that I know you didn't ask, but we probably should talk a little bit about it or they should look at it is make sure that you're doing some level of testing. Right. So we like OMG, Objective Management Group. We like Sales Hunter. We like DISC, TTI and SSI. Right. That's all one. And so just having a firm understanding of how will this person perform, how will this person perform under pressure and what is their level of grit and stick to it? because sales today is taking longer. I mean, there's nothing we could do about it. Every business owner wants a magic wand.

13:57I wish I had it. I'd be really, really, really rich. We'd be going to the next restaurant every day, not just once a quarter, but it's taking longer, right? There's just a phenomenal study that was just done, right? So there's five to seven, if you're selling in a very high intense B2B market, five to seven decision makers on every deal, right? Deals are taking longer. and so you have to kind of realize that and do what you can to accelerate that but you also need some salesperson with some level of grit and stick to it so they could really drive that sale and so you just have to kind of make sure you have the right person in the right environment for how you sell in the products and services but most importantly how do your people buy right so how do your prospects buy and reverse engineer it from that perspective because a lot of times we hire salespeople and they're like, well, they were successful at XYZ, but they're not successful here.

14:51Well, one is XYZ could have been selling into a different marketplace, right? XYZ could have had a much different differentiation in the marketplace. And so you kind of have to realize, who do I sell to and who will be successful in selling to those people? We're big on personality types matched with the industry. And, you know, it's a science, right? But we want it to be an art, but it's really a science. Yeah. Well, Nick, let's share to our friend that's listening. They're like, listen, I need to have a conversation with you because I'd love to kind of map this out. And I suspect that you have some really great resources as well.

15:28Let's let's empower our listener with their next steps. What is next for them? Yeah. So they could go to sales pack sales P-A-C-K dot sales performance team. We give a lot of good resources away for everybody that listens to this. We have a book. You can give us a call. Give us an email at Nick at Sales Performance Team. I'm on LinkedIn. So you could hit me up on LinkedIn 24-7. And you could go to our website and just kind of opt in. We'd be more happy to have a conversation with you. Just mentioned that you heard us on this show. One is so we could give Josh and his team accolades. But also, you know, we'll do something special.

16:01We'll kind of do an audit for them just to say, hey, listen, you got to look at some of this stuff. Yeah. Nick, I'm sorry. What was the book? It's called, we got a couple different ones. So it's the No BS Management of Sales Teams. It's right above me. You can see right there, the ultimate guide to hiring sales teams for small businesses. I've been more than happy to send that out to people. Just send me your address and we'll send a physical copy. It's what I call a airport read, right? Or an airplane read. It's meant to start to finish, wheels up to wheels down to get it finished, right? So there's a lot of good stuff kind of crammed in there.

16:37but it's meant to be a quick read for business owners. We don't have a lot of time. You can get it. Again, that website we have linked up in the podcast shows here. It's salespack, one word, salesperformanceteam.com or you can also just order it on Amazon, The Ultimate Guide to Managing Your Sales Team. Awesome. Nick Luizzi, thank you so much for joining us. Enjoy the restaurant tomorrow night. I will. I will. I'll tell you all about it. so you and your wife could kind of come up and enjoy it. I love it. I love it. Thank you so much for our conversation. Thanks, Josh.

17:17If you've enjoyed this conversation, I'd love to invite you to share your message with the world at podverified.com, where thousands of podcast hosts and thoughtful guests are connecting the right way. Podverified helps match you with the right stages for your level of authority. No more wasting time on brand new shows that just aren't a fit. Your guest authority score is free. And so are your first two podcast matches. Come hang out with me there. I'd love to learn more about your business, support your mission, and help promote you far and wide. Just head to www.podverified.com to get started.

18:00And of course, if you'd like to be a guest right here on The Thoughtful Entrepreneur, just go to upmyinfluence.com and click on podcast. Thanks for being a part of this movement. We rise by lifting others.

From the publisher
How to Build a High-Performing Sales Team in a Founder-Led Business: Insights from Nicholas Loise

For many small and midsize business owners, sales can be both the engine and the bottleneck of growth. Founder-led sales will only take a company so far before scalability demands process, structure, and leadership. In this episode, host Josh Elledge speaks with Nicholas Loise, Founder of Sales Performance Team, who shares practical strategies for transitioning from founder-driven selling to building a high-performing, self-sustaining sales organization.

Building a Scalable Sales System

Nicholas Loise explains that most founders struggle with hiring salespeople because they underestimate how different it is to sell for a small business compared to a large enterprise. Without the backing of a big brand, sales success depends on grit, creativity, and adaptability. He emphasizes that before hiring, founders must document their entire sales process—from prospecting and discovery to objection handling and closing—so new hires have a clear roadmap to follow.

Once the playbook is in place, Nicholas recommends hiring two salespeople at once to increase the chances of success, benchmark performance, and encourage healthy collaboration. He also stresses the importance of investing heavily in the first 90 days, creating structured onboarding, shadowing opportunities, and clear milestones to ensure quick ramp-up and retention. Compensation should be simple and transparent, typically a mix of base salary plus commission that motivates results while providing stability during onboarding.

Finally, Nicholas discusses how to maintain oversight without micromanaging. Delegating sales effectively requires trust—but also process. Regular reviews, feedback loops, and continuous updates to your playbook keep the system strong. By using objective assessment tools and focusing on cultural fit, founders can build sales teams that scale sustainably and deliver consistent performance long after they’ve stepped out of the front-line role.


About Nicholas Loise

Nicholas Loise is the Founder of Sales Performance Team and a seasoned sales strategist who helps founder-led businesses build scalable, high-performing sales teams. With decades of experience in sales leadership, Nicholas specializes in designing sales playbooks, recruiting and onboarding top-performing reps, and aligning compensation structures that drive profitable growth.


About Sales Performance Team

Sales Performance Team helps $1M–$25M companies transition from founder-led selling to a system-driven sales organization. The firm provides fractional sales leadership, sales team recruitment, onboarding systems, compensation design, and proven frameworks that help founders replace intuition with strategy—and build a sales team that consistently delivers results.


Links Mentioned in This Episode


Key Episode Highlights

  • Founders often struggle to hire sales reps because they underestimate how different small-business selling is from enterprise sales.
  • Documenting your entire sales process—from prospecting to closing—is essential before stepping out of the role.
  • Hiring two salespeople at once improves benchmarking, morale, and retention while reducing hiring risk.
  • Strong onboarding within the first 90 days directly impacts sales performance and long-term success.
  • Keep compensation plans simple, transparent, and performance-driven to attract and retain top...

More from The Thoughtful Entrepreneur

All 987 episodes
2294 - How Documented Processes Improve Onboarding and Performance with Sales Performance Team's Nicholas LoiseThe Thoughtful Entrepreneur · 18 min
Listen in VO