In this interview, J. Ryan Williams outlines how he determines whether a company is a good fit for his coaching and growth program and describes the core elements of his playbooks for scaling revenue teams. He begins by emphasizing the importance of ethical alignment, using interview questions (e.g., “tell me about a time you gave a client bad news”) to screen founders who genuinely care about serving customers. He then discusses the need for coachability and a higher‑purpose mindset in founders, noting that technical brilliance alone is insufficient. Williams highlights common scaling challenges such as losing revenue when top reps become managers, and he positions himself as an external sounding board to support leaders’ career development and succession planning. He stresses designing custom training paths that prepare reps for future managerial roles. A major theme is the necessity of mapping the buyer’s purchasing process; founders often neglect to diagram the buyer’s steps, leading to stalled deals. Williams walks through a typical B2B SaaS sales cycle, urging founders to align their sales process with the buyer’s journey and to customize proposals based on real buyer data. He contrasts two playbooks: an early‑stage (seed/Series A) approach focused on buyer‑process mapping and leveraging founders’ prior buying experience, and a post‑unicorn approach that addresses capacity constraints, partnership readiness, and scaling sales teams. Throughout, he warns against opportunistic founders lacking domain expertise and highlights cultural fit—companies driven by impact rather than short‑term gains—as essential for sustainable growth.
Chapters
So I want to kind of go dig deeper into that leadership side. So, you know, with your coaching program, you focus on, you know, high potential revenue leaders and then obviously opportunities of what the business is. How do you assess whether the company is a right fit or good fit for able to hit that projection? And, you know, when you come in and actually get the results?
Well, the first is ethics. I want to make sure that I'm working with clients that have an ethical background and have, you know, a shared value system. One of the ways I did that when I was recruiting salespeople to work on my team is in the interview, I asked my favorite sales interview question: tell me about a time you gave a client bad news. And in that story, you can find out if this is a used car salesman who's trying to lie to you, or if it's somebody who legitimately cares about serving their clients well. And so I won't take on a founder client who's not in it to serve his or her customers well. If they're in it for a quick experiment, those companies never work out. They're backed by some of the best investors in the world, by the way. I've seen it, the no-name company, and I've seen it with the fastest growing Y Combinator exit, yada, yada, yada. I've seen both of those companies start with somebody who goes, I'm just going to try to screw some customers into buying this thing. And that doesn't feel good. I'm not going to ever work with somebody like that again.
Fair enough.
I'm going to try my best to stay out of that. And so when you start to look at the way those companies grow in at the corporate level, I want to make sure that there's this shared philosophy of We're out here because we really want to make an impact. We really want to make a dent in the world. And when that's true, then the next question is, we're growing so fast, you know, we took our best rep and made them a manager, and then we lost a bunch of revenue because that person's not selling anymore. Now they're doing the management tasks. And that manager maybe grows up into a director or VP, whatever the situation is. And so what I do is I come to you know, essentially as an extension of that team to give the sales leader an outside sounding board, the ability to work with somebody on their own career development because they're not getting their one-on-ones anymore with their boss. They're getting board meeting prep meetings. They're getting, oh my God, what are we going to do meetings? They're getting spreadsheets to go over with the rest of their leaders and peers. And they're not getting the, what do you want from your career?
Hmm.
How do you make that happen here? What is your dream for this team? You know, one challenge that comes up quite frequently that honestly I wish this would come up more is the identifying somebody in the succession plan. If I get promoted to VP, I'm going to need another, you know, manager on my mid-market team. How do I make sure she's ready?
Right.
You know, and so I work with them to design custom training plans. Okay, well, here's a rep who needs to maybe move into hiring, maybe they move into interviewing, so then they have that skill by the time they become a manager. And that's the thing that, you know, as companies we scale, we think, okay, so if this works, I'm going to need X server capacity, or when this works, I'm going to need to make sure that I've got these partners ready to go. And so we go and kind of sell before we're ready on partnership, on engineering, on product. But in sales, we're often playing catch-up.
True.
We don't hire before we're ready on sales. And so I really— I work with my clients to make sure they've got the capacity to keep thinking big even on the sales side where you might feel like you're playing catch-up. How do I get enough reps? How do I get enough revenue? But really it's about how do I develop my people in a way that they'll have the capacity to lead when the time is— they're called on.
It makes sense. You know, when you're working and deciding who you want to work with, what would you say is an ideal founder profile or executive you like to work with and coach? And what would you say are the key differentiators of the best performers from the rest? Is there some kind of key traits or some things you notice on the ones who do better than the others?
Well, the trait is— the traits are interesting because, you know, everybody will say you got to find a smart founder, you got to find a brilliant team, look for teams that have unfair advantage. Okay, so let's assume all those checkboxes are there. Then the next question is, are they coachable? Because many founders that are great are actually not very coachable. Now, I'm not saying coachable means you need to listen to what I say and then go do it. I think a lot of investors would actually think that I need them to be able to do what they're told. That's not the way I'm going to join an advisory board for you. That's not the way that I'm going to be a coach for you. Part of my coaching philosophy is very supportive, yet giving clients the space to do what they want to do, take their path of self-determination. That's an important trait. And so I look for founders, and when I'm evaluating people to work with, it's, is this founder somebody who actually wants to go win? And maybe they're scared of it. That's fine. We've all been scared of success. But they want to go in because they believe in a higher calling. The industry needs this. One example is somebody who has a product that helps small businesses save about half a million dollars a year in an expense that most don't know they have. Well, let me help them go reach a bigger audience. Let me help them build a sales team and make sure they hire and groom the right talent. Let me make sure that they're going— when they go upmarket, that they're ready to do a deal with a big partner, right? Like a Fortune 5 financial partner that they did a deal with. Let me go make sure that that founder is able to stand square and go do that deal rather than have their breath held, not knowing what their value is. Those are all things that I'm looking for, but that's kind of a convoluted answer to what you said, like trait-wise, It's really somebody who feels like their solution is going to be, you know, going to fit in this bigger story about moving, you know, moving technology forward, you know.
So it sounds more it's about like they have that belief in themselves and what they're selling and more that they're actually adding real value to what they're— the end user.
Yeah, you know, building something people need, right? You know, I don't think that, you know, I think YC is wrong when they say just make something people want and everything else falls into place. That's not the way software is sold, by the way. But if you start with, I know that this is why this is needed, great. You know, I talked to somebody the other day, fascinating business, fascinating opportunity, really interesting guy, somebody I cannot wait to get a beer with, but fell into the industry, fell into the product, fell into the team, and now raising a monster round. And, uh, he's, you know, he's very far from his user in that it's not, not a space he— it'd be like if I got into, like, I don't know, knitting software. Like, I don't know anything about crochet, quilting, or knitting. Like, I like to do projects, but that's not my world. If I told you I was going to do the next amazing quilting apps, you know, if I was going— if I was going to be the next Craftsy, which is a really interesting business, well— If I tell you I'm doing that and I have nothing to do with that space, you should be suspicious. This is the same type of thing.
Right. There's different type of people, right? They just chase opportunity, they chase the money, and they'll find the right people around them to—
Yeah. You know, when the company takes off and it's doing really well and you get listed as the best place to work, or you get listed as an Inc. Magazine fastest growing company, or you get on the Forbes, you know, Cloud 100 list, or Or those types of things. Well, who shows up? Well, it's those IPO hunters who show up, and they're a leadership version of the same founder problem that I just described. They're only there because they think it's going to be a good party. And I would rather somebody who comes because they know they can make it a better party.
Right.
You know, and that's apparent when somebody shows up to your house. You can tell by the booze they're contributing to the minibar on what— on the way they think of themselves. You know, hey, I brought this wine that I can't wait to have with you because this is my favorite vintage or favorite place or whatever. Doesn't matter even if it's $10, like does not matter.
True.
That person I will always take over somebody who shows up and it's clear they just, they grabbed something in the corner store, it was the closest thing they could find, it was on sale, whatever. And they showed up and they're like, oh wow, you guys, you guys have this over. Yeah, don't open my thing, let's open that nice thing of yours, you know. Or the something that somebody else brought in. It's like, no, come, come to bring part of the party with you.
Yeah.
And we'll be, and we'll be fine.
I love it. Share the joy, man. Can you— so you find the right finder, you found the right founder, the executive to work with, you found the right company that you think you can generally help, and you feel they're making an impact and helping their end user. Now you're coming in there, can you share what is your general playbook growth playbook look like? What's the most frequent improvements required from, you know, the wide range of clients you work with and companies, and how do you work with them to achieve that, the development goals or leadership goals and ultimately growth, right?
Well, I'll give you 2. One at the kind of seed stage founder level, like let's say, let's call that Series A and below. And then I'll give you another example of what to do when you're an Airbnb or a Lyft and you're post-unicorn And then hopefully you can think about the spectrum between there as some ways to do maybe both or a mix. So in the early stage, the biggest problem that I see is somebody who's selling— and mind you, my experience is mostly B2B software, a lot of SaaS.
Yeah.
Most founders in this space don't know or don't realize what they already know about their customer buying process. And so if you're a founder listening to this today and you're thinking, oh man, what does he mean? Well, we'll take out a piece of paper and draw out your sales cycle. Okay, so in the sales cycle, the first step is we get a cold call. Maybe it's an introduction because my investor has introduced me to somebody in procurement at IBM. Okay, so I write down introduction as step 1. Step 2, after the introduction, I'm maybe going to do a demo. Maybe I want to show them the software. Maybe I'm going to ask them some questions or customize that demo. And there's maybe 5 or 6 steps in that process. Now, the founder who's learning about B2B sales has also learned from books like The Challenger Sale that there's around 6 or 7 decision makers on the other side of that deal in enterprise software, right? So identify those people too. But here's what most people are missing. Most people aren't sitting and diagramming that same process for the buyer. So put your buyer hat on and, and what is step 1? I got introduced to this person. I don't know what the offer is. Step 2 is make sure that offer is real. Go around and figure out if we truly have the problem that the software is solving. So I might interview department heads. I might bring it up at the management meeting. I might tell my employees about this thing that I heard about if I'm a senior leader and I'm bringing in a tool that I'm not the user of, right? Like how many SVPs of sales are truly Salesforce users? They're report readers, but they're, they're, they're not adding stuff into Salesforce. So they're not going to be the people who like buy outreach, or buy Scratchpad or buy these other tools that make a sales rep's life easier, they're not going to be the user of that. They may buy those things, but they're not the user of that. Right. And so think about that. Right. So if you're selling into this top dog and that person brings it down to their team, what does that conversation look like? So, so at the early stages, you have to diagram what the buying process looks like so that you can identify if your sales process is in lockstep with what your buyer is doing. Because a lot of times what'll happen is, you know, I'll meet people who get stuck in a deal and they'll call up and they'll say, I can't figure out why this deal is stuck. And we'll talk about it for a little while and they'll realize that what's happening is on the other side of that deal, someone is still walking around trying to get an internal buy-in. And we never gave them the tools to be successful at that. You know, we sent them a proposal, but we never said, hey, here's how we can customize this proposal. So can you ask this team or that team? You know, I used to sell hotel software and we'd get so detailed to say, can you just, before our next meeting, will you ask the director of housekeeping how many people will use this app on her team?
Right.
Well, now we can customize that proposal around real data that actually drives change for the client, right? Like they want that. And the kicker that just, it just makes me smile every time it comes up is oftentimes the best founders are the ones that came out of middle and big businesses. So, you know, I worked with somebody who is the head of engineering for one of the Microsoft teams.
Okay.
I won't tell you which one, but he's a super founder. He was amazing. But he had been a buyer of his own tool. Then he leaves Microsoft, he goes and starts this new company. And we spent a lot of time turning around. I said, when you were back in your last job, draw out the process of the last 5 things you bought. Now let's build a sales process that looks the same because You're selling to your old self. So who better to know about that than you? You know whether or not you got buy-in and you know whether or not your boss would give you $1 million or not. You know, another stat around this that most founders don't believe and I always share is I had done a little bit of coaching and work with a founding team that previously was at Salesforce.com. And she was a director and said, you know, as a director at Salesforce in this particular division that she was in, she had autonomy to spend $300,000 on any tool that was already budgeted.
Wow.
Great. Check that box. I said, okay, well, what about your boss? Oh, well, he could spend $1.5 to $3 million as long as it was in the budget. And but the question that had come up for the founder was, hey, how do I price my tool? Since you're selling it back to your old self, how much could you have bought it for? You know, and that's where the light bulb goes on. And so any founder listening to this, if you haven't diagrammed that buying process yet, even if you'd worked in that business or not, it doesn't matter. But if you diagram that buying process, you're going to see opportunities to change your sales process around what your customer actually wants.
