Your Sales Comp Plan Is Costing You Millions | Dan Pascone with Kyle Smith | Podcast #20

Posted on June 21, 2025 by Dan Pascone

Answer Box: TL;DR

Most sales comp plans quietly burn money and demotivate the very reps they’re supposed to inspire. In this episode, Dan Pascone and sales consultant Kyle Smith break down how misaligned quotas, overly complex plans, and the wrong base/variable mix can stall growth, drive “shadow accounting” behavior, and create nasty surprises for finance. Kyle explains why simplicity, attainability and clear attribution are non-negotiables, why more of OTE has shifted to base in the last decade, and how leadership comp and equity expectations have changed post-COVID. He also shares his personal money journey—from being “sick of being poor” to engineering an employee buyout of The Bridge Group—and the mistakes he’d never repeat (like financing cars instead of investing).

Key Takeaways

Incentive comp should be the steering wheel, not the mystery box. A good plan is simple to understand, clearly tied to the company’s top objective, and avoids turning reps into part-time accountants trying to self-audit every payout.
Quota attainability matters more than heroic targets. Kyle uses 65% quota attainment as a healthy benchmark. If significantly fewer reps are hitting quota, the plan stops motivating and starts feeling rigged—leading to churn and underperformance.
The base/variable mix has steadily shifted toward base. Over roughly a decade, AE plans have crept from 50/50 to ~55/45, and SDR plans from ~60/40 to closer to ~67/33 in favor of base. Drivers include intense recruiting competition and finance teams wanting to avoid uncontrolled accelerator risk.
Leadership comp is wildly inconsistent. VP and CRO total OTE can vary from ~350k to 700k+ with similar titles. Equity still matters, but after a cycle of down multiples, dilution, and failed exits, many leaders are less willing to take big cash haircuts for “maybe” money.
Most sales orgs carry “process debt” just like technical debt. Early-stage hacks and one-off fixes often linger as a company scales, creating a messy patchwork of roles, territories, tech, and comp that isn’t truly scalable or repeatable.
Money habits matter as much as income growth. Kyle’s early “I’ll just make more” approach led to car flipping and lifestyle creep. His later pivot to maxing out retirement, investing after-tax, buying his firm, and paying cash for cars dramatically changed his trajectory.
Clear goals anchor financial decisions. Instead of chasing status symbols, Kyle and his wife now aim for a $5M net worth and an eventual short-term rental beach house in Maine—choices that influence how they save, invest, and spend today.

Key Moments

00:30 – Meet Kyle and The Bridge Group. Dan introduces Kyle Smith, Managing Partner at The Bridge Group, a B2B tech sales consulting firm focused on org design, comp, and playbooks.
03:14 – How engagements actually work. Kyle explains their project-based model, deep discovery process, and how they immerse themselves in client data, interviews, and call recordings.
04:49 – “Technical debt” in go-to-market. Kyle compares sales org structure to technical debt: hacks that worked at $1M revenue often break at scale, especially after funding rounds.
07:15 – Comp plan diagnostics. How The Bridge Group evaluates base/OTE splits, incentive mechanics, and alignment to company goals—and why six-page plans are a red flag.
08:13 – 65% quota attainment as a rule of thumb. Kyle shares his benchmark for healthy quota design and why metrics must be trackable and within a rep’s control.
09:12 – The drift toward higher base pay. Trends in AE and SDR comp mixes over the last decade and why post-COVID recruiting and accelerator risk pushed more dollars into base.
12:09 – Exec comp, equity, and changing expectations. Why VP/CRO OTE is “all over the map” and why many leaders are less willing to trade big chunks of salary for equity after seeing multiples fall and exits stall.
13:52 – From biology major to sales junkie. Kyle’s family of entrepreneurs, his aversion to being broke, and the mentor (his aunt Trish) who pushed him toward sales.
15:49 – Falling in love with sales. Within two weeks of his first outbound role, Kyle was hooked by the direct connection between effort and income.
17:30 – Engineering an employee buyout. How he and colleagues proposed and structured a multi-year buyout of The Bridge Group from founder Trish, starting with a 4% stake in 2018.
19:47 – The expensive car lessons. Kyle’s early habit of constantly leasing and flipping cars, and the mindset shift to paying cash for certified pre-owned vehicles and driving them for years.
20:52 – Future goals: net worth and a Maine beach house. The couple’s target of $5M net worth and a short-term rental property they can both use and treat as a business.
21:26 – Lightning round insights. Coffee over tea, pasta for life, Zoom as indispensable tech, and favorite books like Grit, Disrupted, and Dave Ramsey’s Total Money Makeover.

Episode Summary

Episode 20 of the Making Sense of Your Money podcast zeros in on one of the most sensitive—and powerful—levers in any revenue organization: the sales comp plan. Host Dan Pascone sits down with Kyle Smith, Managing Partner at The Bridge Group, a consulting firm that helps B2B tech companies design scalable sales orgs, build playbooks, and structure compensation that actually drives results.

Kyle explains how many go-to-market systems accumulate “process debt” as companies scale. What worked when there were a handful of reps and $1M in revenue doesn’t necessarily work at $50M, especially after a funding round. The Bridge Group comes in on a project basis to assess org design, roles, tech stack, and compensation, then recommends a clearer, more repeatable structure.

On comp, Kyle emphasizes that incentive pay is there to shape behavior. Effective plans are simple, understandable, and aligned with top-level business objectives. He looks for healthy quota attainability (roughly 65% of reps hitting quota), metrics that are trackable and within a rep’s control, and a base/variable mix that both attracts talent and protects the company from wild accelerator exposure. Over the past decade, he’s watched AE plans inch from 50/50 to ~55/45 and SDR plans from ~60/40 to ~67/33 in favor of base, driven largely by competitive hiring markets and post-COVID risk concerns from finance.

At the leadership level, compensation is far less standardized. VP and CRO roles can range from the mid-300s to 700k+ in OTE, often with variable levels of equity. Importantly, Kyle notes that after a cycle of lower revenue multiples, dilution, and fewer blockbuster exits, many executives are less willing to take major cash pay cuts in exchange for equity that may never pay out. People still care about ownership, but they want to be paid fairly in cash today.

The conversation then pivots to Kyle’s personal financial journey. Growing up around small business owners and constant conversations about scarcity, he initially chose sales simply because he was “sick of being poor.” He quickly fell in love with the direct link between hustle and income, but spent his early years chasing cars and lifestyle upgrades rather than building assets. Later, he course-corrected: maxing out retirement accounts, investing after-tax, paying cash for reliable cars, and ultimately working with colleagues to buy The Bridge Group from his aunt, founder Trish. Now his focus is on building a $5M net worth and eventually adding a short-term rental beach house in Maine—using the same clarity and discipline he advocates for in comp planning.

Full Transcript

(00:02) Dan Pascone: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Dan: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders to make smart, confident money decisions. Welcome to episode number 20 of the Making Sense of Your Money podcast.

Dan: I am your host, Dan Pascone. I’m the founder and CEO of Tailored Wealth. And each episode on our podcast features a trusted voice in the financial world, someone who works directly with high-level professionals to simplify the complex and turn strategy into action.

Dan: I’m pumped about today’s guest. We’ve got with us Kyle Smith, who is a Managing Partner of The Bridge Group. And Kyle and his team do sales consulting for B2B tech companies, which is near and dear to my heart because I came from a sales leadership background.

Dan: So, thanks for joining us on the Making Sense of Your Money podcast, Kyle. Pumped to have you today.

Kyle Smith: Appreciate you having me on.

Dan: Yeah, you bet. You bet. All right, so we’ve got a lot to cover. Kyle’s going to share a lot of different things with us today—I’m excited about it professionally and personally.

Dan: Just do us a favor, Kyle: quick 90-second overview of who you are, what your firm does, and what kind of got you into that field.

Kyle: Absolutely. Kyle Smith, Managing Partner of The Bridge Group. As you just said, we are a sales consulting organization, which can mean a hundred different things, but basically what it means for us is that we help technology companies to sell more of their tech.

Kyle: That looks like strategic assessments, which involves organizational design—like how many headcount in what roles, compensated in what ways, supported by what technologies, playbooks, tactical how-to guides—and then we do some interim management, training, coaching type services.

Dan: Very, very cool. Listen, there’s a lot that we could certainly unpack there. Tell us a little bit about how you got into this field and sort of your progression at the firm.

Kyle: Very accidental. I have a degree in biology. I thought that I wanted to pursue an advanced degree in life sciences and realized I was really sick of being poor.

Kyle: I reached out to a mentor who suggested that I give sales a shot. Did that. That person’s name was Trish Petusi. Two years later, I called her back and asked what I should do next—like which company should I go work for—assuming she was going to make a recommendation of a tech company.

Kyle: Instead she said, “Why don’t you come try to do consulting?” And that was 2014. I joined The Bridge Group on a whim. I said, “We’ll test this out,” and 11 years later here I am, now as owner.

Dan: I knew The Bridge Group sounded familiar to me, Kyle. I don’t think I told you this before, but I actually know Trish Bertusi. So, given my background and my corporate career, I spent a lot of time around great people like her.

Dan: All right, so that’s amazing. Let’s talk a little bit about your work. At Tailored Wealth, we deal with a lot of folks that are in revenue-generating functions, so a lot of our audience is going to be familiar with what you do.

Dan: Let’s talk a little bit about the comprehensive sort of nature of your services, because in that brief intro what you talked about seems like it’s a bit more in-depth than most sort of “sales consultants,” and I know that can mean a lot of different things.

Dan: So, tell us a little bit about your process—how you engage with a client and then ultimately what you help them to achieve.

Kyle: Our process starts with a pretty rigorous and regimented discovery—like traditional sales process discovery call—figuring out what are we going to do. We don’t do a whole lot of, like, less than 5% of our work I would consider retainer-based or ongoing time-and-materials-based work.

Kyle: So everything—almost everything—we do is project-based. We have really specific scopes of work with deliverables attached to it that we’ll execute over a certain time frame.

Kyle: In terms of the depth that we’ll go to, we’ve done anything from extremely complicated, nitty-gritty, detailed org design for a 3,500-person global sales org, down to a really specific small subset—like, “We will just build one outreach cadence for an inbound-only SDR team,” right?

Kyle: So it can be really broad and be everything, or it can be really specific in a singular thing. But in every single engagement, we go through the same process, which is in-depth immersion—understand their business to the best of our ability as outsiders.

Kyle: We do that through interviews, review data, review all existing materials, listen to call recordings—anything we can really get our hands on to try to see the world through our customer’s eyes.

Dan: Very cool. Very cool. All right, so let’s unpack that a little bit. I’m sure it varies and I know each customer is very unique and different, but tell us a little bit about the top challenges that your clients typically face and how you help them to overcome those challenges.

Kyle: Usually number one would probably be the equivalent of technical debt. You know, when you are scaling up an organization, everyone talks about technical debt, which is basically a bunch of hacky workarounds that were created by the six people in the roles that came before you.

Kyle: There’s something similar as it comes to process and structure for a sales team, which is: you have something that’s in place when you’re a $1M company, when you start hiring salespeople, and then it slowly evolves over time and you kind of hack it together to make it work for every single stage of your evolution.

Kyle: But then at some point—typically some inflection point, like you just took on a round of funding is a great example—and now you need to actually scale in a more intentional and meaningful way. That would be a time when we would get hired to make sure that the structure makes sense, is repeatable and scalable, because it feels a little bit fragmented or all over the place, or growth is stagnated, performance is dipping, and the individuals in the business aren’t exactly sure why.

Kyle: Sometimes it’s just an outside pair of eyes, ears, and hands to say, “What’s actually going on here and how do we fix it?”

Dan: I’m curious—what roles at the organization are you typically engaging with? I’m sure it varies based on the size and scale and maturity of the business, but are you getting hired by the CEO? Are you being brought in by the CRO? Tell us a little bit about who you’re working with in your engagements.

Kyle: If you’d asked me 5 years ago, CEO was much more prevalent. In recent years, we’ve—just not overly intentionally, to be brutally honest—but we’re working with larger organizations. So, significantly fewer startups than we did previously.

Kyle: So way less CEOs hiring us now. Still some, but not the same level of frequency. Primarily you’re talking CRO, Chief Revenue Officer; VP Sales; VP Marketing.

Dan: Very cool. And you’re just coming in and sort of analyzing all aspects of the revenue function, and for each client they’ve got a different outcome that they may be looking to achieve. I get that it’s always to produce more revenue, but their problems are going to vary.

Dan: All right. So let’s talk about a couple of things. You mentioned comp plans, and I know that’s something that your team oversees, and having been a former CRO I understand how important that is.

Dan: Tell us a little bit about the work that you do in that space. And then what are some of the challenges that you find when you’re analyzing the comp plans of either the sales team—the actual boots-on-the-ground sales team—or the sales leadership team?

Kyle: Yeah. So if you’re hiring somebody like us, you already have a sales team. We’re not building something from scratch, so we’re always going to be making an adjustment to something that’s pre-existing.

Kyle: As part of that process, we’re going to identify: how does the comp plan line up to industry benchmarks in terms of the raw basic numbers? So base/OTE splits between base and incentive comp. Are we in line with what that total number equals in terms of market rate?

Kyle: And then once we get into the incentive compensation details—incentive comp drives behavior—so are we actually driving the behavior that the company has told us we want? There’s some big picture or overarching objective that the company is trying to accomplish.

Kyle: The goal is to just make sure the incentive comp plan that’s handed down to sales reps aligns to that goal. Big things that we’re looking for are: how do we not turn this into a shadow accounting nightmare where reps are spending two hours a week in their own G-sheet trying to make sure that they have proper credit and that they even know what they’re getting paid?

Kyle: Simplicity is a key factor in that. Make it easy to understand. If I have a six-page compensation plan agreement, we’ve done something horribly wrong and we’ve made this way too complicated.

Kyle: So simple—core pillar. Second thing would be attainable. In general, 65% of reps should achieve quota on any given team. We want to make sure that looking at historical data, and again benchmarks, that that’s something that’s actually achievable—the quota is.

Kyle: And then the next piece would be: largely in their control and possible for tracking. Can we actually tie proper attribution to the compensation plan, and are the factors that the reps are being compensated on within their control?

Kyle: Those would be some of the basics that I would look at right from the start.

Dan: Makes a lot of sense. I’ve seen that in my own career. What is your take on—and maybe what are you seeing as far as benchmarks and standard for today’s split between base and incentive pay?

Kyle: Every year for the last 10 years, more has been going to base. We collect benchmarking data on this, and the AE—Account Executive—like new-business closing role was always, forever and ever, 50/50.

Kyle: And now it’s like 55/45. So it’s not moving dramatically—we’re not seeing these huge shifts—but a half-percent increase shifting to base every year for 10 years means all of a sudden you’re at 55/45, which is interesting.

Kyle: Same with the SDR role—actually more heavily weighted on base than it was previously. It used to be 60/40; now it’s like 67/33.

Dan: Do you see that as a recruiting tool? What do you think is driving that?

Kyle: Recruiting—largely or mostly that got ramped up more significantly in that post-COVID boom time. Remember, I’m tech, so that’s the world that I know. Post-COVID, tech was on a wild ride. Everyone was just shooting to the moon and it was impossible to get talent.

Kyle: So I think yes, you’re right—part of it is a recruiting tool. I think the other part is, especially within certain orgs, having more on the incentive comp side—with accelerators—can actually introduce unnecessary risk exposure.

Kyle: If you don’t have a wealth of historical data to base quotas on, and you’re just kind of basing it on benchmarks, somebody goes and blows it out of the water and you were aggressive with your accelerators, then all of a sudden you’re cutting some crazy checks, which, if somebody’s overperforming, is not a bad thing.

Kyle: But that could be part of it: finance says, “We need some upside protection, not just downside protection,” which can lead to, “Let’s just give them more base and be a little bit more conservative on the incentive comp.”

Dan: Makes sense. How about as you go higher up the food chain in sales—to your manager level, your director level, your VP, up to your Chief Revenue Officer? Give us some thoughts on the comp dynamics at those levels.

Kyle: Yeah. The individual contributors are pretty formulaic. I can tell you with a high degree of accuracy what the comp plans are likely to look like before I see them.

Kyle: When you start talking about second line or executive leadership, there is no consistency whatsoever. They are all over the map in terms of the total number, meaning the total OTE.

Kyle: You could tell me somebody’s a 350k VP of Sales or somebody’s a 700k VP of Sales and I would be not at all surprised in either direction for certain companies.

Kyle: So those are all over the map. Still 50/50—probably closer to 50/50 plans of base and incentive comp. Then it gets into: what stage of evolution is the company at, and then how much are they going to give in terms of a slice of equity and where are they going to offer the upside and get you bought in.

Dan: Tell us a little bit about how you’ve seen the evolution of equity comp at those higher levels, specifically within sales leadership, post-COVID boom. What have you seen in the last few years? Have there been any trends relative to equity compensation?

Kyle: I’d say less from the company side—I think the companies are managing it in an extremely similar way. I would say more from the applicant side, or the leader side—not chasing that shiny object the way that I noticed that they did 10 years ago.

Kyle: It was like, “Wow, I know 30 people who have been part of some eight-figure exits and I want to jump on board that.” More like, “I know so many people who took 150k a year less than their market value would demand for equity that never materialized—three times over.”

Kyle: So they’re not doing it now anymore. There’s less people who are like, “If I have job offers on the table and I say based on my experience and all the things that I’ve done, I’m a 450k resource, I’m not going to take 300 because you’re going to give me 2%.”

Kyle: Because of dilution and where are we going to? There’s less acquisitions happening, and the multiple came way down. We were seeing 13–14x multiples and everyone could go get sold or go public—not as many public, but acquisitions were happening like crazy.

Kyle: Now you’re seeing like 6x revenue multiples, still with dilution happening, and so it’s not as appealing. I don’t know if it’s the reality of the situation, but my take on the perception of the situation is that I think fewer executives think that they are racing towards an easy $10M exit from their slice of equity.

Kyle: So they want to get paid now for what they’re worth.

Dan: That definitely checks out in the work that we do, and that makes a lot of sense. That’s well said.

Dan: All right, let’s shift gears a little bit, Kyle, and I want to talk a little bit about your sort of financial story. You started off by telling us you had this career path and you decided you didn’t want to be poor anymore.

Dan: I want to unpack that a little bit, and I too had a similar journey early on in my career where sales was something that was attractive from a financial perspective and from a job perspective.

Dan: What really got you into that, and then tell us a little bit about your financial evolution from when you started to where you’re at today, which is as a Managing Partner of the firm.

Kyle: Yeah. So my family—I come from a massive collection of entrepreneurs in every type of business you can imagine. A lot of blue-collar contractors: plumbers, electricians.

Kyle: My mom and aunt owned an airport shuttle service in the pre-Uber days that they ran. A ton of just small business owners. An uncle owned gas stations. We have some franchise owners, stuff like that.

Kyle: So I use as the backdrop my extended family—bunch of entrepreneurs. My immediate family, money was always a topic of conversation and it was always something that there wasn’t enough of.

Kyle: Then you’re in college. That’s up through the first 18 years of life. Then you have college where, for the most part, everyone’s poor. So at that point—you’re 22, I was 22—and I mean it, I was so sick of being poor.

Kyle: I just wanted disposable income, or not feel like everything was just a constant struggle. Which is why I started opening my eyes to opportunities to earn rather than going down the graduate school path, which is what it would have taken if I stayed in life sciences and pursued, let’s say, a PhD.

Kyle: That would have been five more years at a minimum of poverty, which I just wasn’t okay signing up for. So it wasn’t my idea to pursue sales; it was Trish’s. Trish said, “Buy sales—I think you’d be pretty good at it.”

Dan: And how do you know Trish?

Kyle: Trish is my aunt.

Dan: Oh, okay. Very cool. Very cool. Got it, got it. Okay, that makes a lot of sense.

Dan: All right. So you get into sales now. Was it an immediate fit? Is that something that—

Kyle: Oh, I fell in love. Yeah, I was addicted immediately. Right away. I mean, two weeks in—one week of onboarding and then they handed me a phone. Then one week of calling, and I think I booked probably like two meetings.

Kyle: I worked for an outsourced sales development shop that had technology companies as clients, and I got hooked immediately because right away I started figuring out that my effort could directly correlate to my income—which is right up my alley.

Dan: Me too. Very cool. Very cool.

Dan: All right, and so now lead us down the path to you getting ownership in your own firm. Tell us about what’s on your financial journey now. What’s important to you from a financial perspective now?

Kyle: Yeah. Investing and not spending right away. When you don’t have money—don’t have money, I say I don’t want to be poor, and then great—then you start actually making halfway decent money and immediately first reaction is: spend that money.

Kyle: Which is—and I went, like many of my friends went down the path of vehicles first. I was like, I’m renting a room in my buddy’s house and I’m just buying cars.

Kyle: I went through five cars in five years. Just kept flipping leases, just spending—not any nice cars, but just like, “I’m going to get a new car every single year,” just burning money on cars.

Kyle: Bought a house, quickly realized that that was a better move than keep buying cars. Then started saving money knowing that I wanted to do something—I didn’t know what.

Kyle: I wanted to do something meaningful with the money—buy a business. Then it just so happened that Trish was getting later in career, starting to think about what the long-term succession plan would be.

Kyle: I knew I didn’t have enough money myself and couldn’t even probably get it financed to where I was at that point, and approached some of my colleagues who were also employees at The Bridge Group and said, “What if we structured an employee buyout?”

Kyle: Rather than letting this thing go to somebody else who would want to buy it, let’s keep it. And so we approached Trish with an offer. I started in 2018; I bought 4% that year. And then took a controlling interest 2–3 years ago.

Dan: Good for you. Congratulations on that. That’s very cool.

Dan: All right. Tell us a little bit about your investing journey because I’m sure that was an important piece of getting the capital necessary to start to take ownership in your now business.

Dan: Talk to us about your theories around investing, what you’ve done from an investing perspective, and how you’ve sort of set yourself up to have the necessary savings to own your own firm.

Kyle: Yeah, I didn’t have a strategy until the last five years. It was basically “make more money.” That was my strategy. Anytime there was a need, it was exert enough effort to make enough money to be able to fund what I wanted to fund.

Kyle: So there was no long-term strategy at all. It was a never-ending game of “make more, make more, make more,” which you can only do for so long. It’s easy through the first six years of your career because you’re on almost an exponential growth curve, but guess what—that thing doesn’t go forever, for the vast majority of us.

Kyle: Unless you’re, whatever, Jeff Bezos or something, I guess. But it just stops, right? So you have to figure out, “What should I actually be doing with this?” because I can’t just keep chasing higher income potential.

Kyle: Up until that point, that was the strategy. Five years ago, I did—I do super boring, which is basically max out 401(k), both my wife and I, and then try to do at least, for us, 40 grand a year in post-tax investments, and then the business.

Dan: Got it. Got it.

Kyle: And she’s in grad school, which I have chosen for my own sanity to call an investment.

Dan: Okay, I like that. That’s a good mental framework. I’m with you on that one.

Dan: All right, that makes sense. That makes sense. As you’ve come along the way, anything you would have done differently from a financial perspective knowing what you know now?

Kyle: Yeah. Not bought any cars. I had a Ford Taurus with like 100,000 miles on it when I graduated. It would have worked just fine. I could have driven that thing for at least three or four years.

Kyle: And then I will never finance a car again. So my wife and I both have only made cash car purchases, and we hang on to them until repair costs start to escalate.

Kyle: We buy certified pre-owned, we buy cash, and even if you could get a low-rate loan, I just won’t ever finance a car again. It changes your decision-making process also on what you buy.

Kyle: It’s really easy to make an overreach if you’re like, “Oh, that’s 50 bucks a month. Oh, that’s a hundred bucks a month.” It’s a lot different when you’re like, “I’m going to cut a check for 35,000.”

Kyle: You’re like, “Oh yeah, but that next thing—the one with the sunroof—is only 42.” You’re like, “$7,000? I am not giving you $7,000. The other one’s fine.”

Kyle: Those minor differences change our decision-making process, which is how we roll with it now, which has been really helpful. You just make more conscious decisions.

Kyle: And we set, like, not exactly a vision board but the same general idea. I want a— We just had a daughter.

Dan: Congrats.

Kyle: Thank you. I want a short-term rental beach house at a town that I like to go to in Maine. That’s what’s next. That’s what I want to do next.

Kyle: So that free cash flow is going towards saving towards an aggressive down payment on something like that that we’ll go to, whatever, a couple of weeks a year, but largely treat as a short-term rental.

Dan: Yeah, it’s great. We had on our podcast a guru of short-term rentals, Shawn Moore. He was on two episodes ago, and he’s got a great framework. You should check him out—he’s got a great framework for short-term rentals.

Dan: All right, so we’re going to shift gears now and go into the lightning round, all right? So we do this on every episode. The idea is: just give us the first thought. Could be one word, could be a long, drawn-out thought. We don’t really care. Just give us the first thought that comes to your mind. You ready?

Kyle: Mhm.

Dan: All right, let’s do it. Coffee or tea?

Kyle: Coffee.

Dan: If you had to eat one meal every day for the rest of your life, what is it?

Kyle: Pasta.

Dan: Okay, like it. What is one tool or piece of technology—could be hardware or software—other than your computer or your phone that you can’t live without?

Kyle: Zoom.

Dan: Zoom. Okay, I’m with you on that.

Dan: Favorite quote or phrase about money or success?

Kyle: I’m probably going to misquote it, but Angela Duckworth in the book Grit said, “Excellence is achieved through monotony.” Something like that.

Dan: Really good. Grit‘s a good one. Yep, that’s a good one.

Dan: Do you have a favorite book on either finance or business for that matter—or sales?

Kyle: I actually don’t mind—I like a lot of the core principles in Dave Ramsey’s Total Money Makeover. I like some of the “just don’t spend like the vast majority of Americans do” type of mentality.

Kyle: My favorite book on business is Disrupted, I think it’s called.

Dan: Yeah.

Kyle: Do you know that one?

Dan: I do. I do. Yep, I read that a little while ago. Yep.

Kyle: It’s hilarious.

Dan: Do you have a personal hack—could be finance or otherwise related. Do you have a hack you can share with the audience?

Kyle: No. Unfortunately, I know that the “avocado toast” thing gets a lot of negative press—like, “Stop buying avocado toast and I’ll be able to afford a house that’s whatever, four times as expensive as boomers bought for”—but I actually do think that that stuff matters.

Kyle: I think all of those small decisions do add up in $50 increments, and it’s not only the $50,000 ones.

Dan: Sure. Yep, I agree with you.

Dan: What’s one bucket list item that you’ve already accomplished?

Kyle: Maldives.

Dan: Very cool. Very cool.

Dan: What’s one financial milestone that you’re currently working towards?

Kyle: Net worth of 5 million.

Dan: There you go.

Dan: If you could give advice to your younger self, what would it be? Give us something other than buying the cars.

Kyle: Save money.

Dan: Okay, I like it. I like it.

Dan: All right, and then finally, Kyle—this has been great—finally, if our listeners and viewers want to connect with you, collaborate, potentially work with The Bridge Group, what’s the best way for them to reach out and connect with you?

Kyle: Reach out to me on LinkedIn. That’s where I do the vast majority of communication, just period.

Dan: Very cool. Me too.

Dan: All right, Kyle, thanks so much for sharing your time and your insights today. We covered a lot. Really appreciate your thoughts and perspective.

Dan: That’s it for the episode. As always, keep your strategy sharp, your goals clear, and your money working as hard as you do. Cheers.

Resources & Citations

Sales Compensation Design Basics. Guides that explain core concepts like OTE, base/variable splits, accelerators, and quota attainment benchmarks for B2B sales teams.
Benchmarks for SaaS & B2B Tech Sales Roles. Industry surveys outlining typical pay ranges and comp structures for SDRs, AEs, and sales leadership roles.
Sales Org “Technical Debt” and Scaling. Articles on how early-stage sales hacks and ad hoc processes can hinder growth and how to restructure for repeatability.
Equity vs. Cash for Sales Leaders. Commentary on how changing market multiples and exit dynamics affect how executives weigh salary versus stock.
Personal Finance for High Earners. Frameworks for moving beyond “just make more” toward structured saving, investing, and business ownership.

FAQs

How do I know if my sales comp plan is “too complicated”?

A practical test is to ask a rep to explain their plan back to you in two minutes or less. If they can’t clearly tell you how they earn commission, what triggers accelerators, and how they get credit on deals, it’s probably too complex. Extra red flags include reps running their own spreadsheets to “check” payroll, frequent disputes, and managers having to regularly interpret the plan on one-off calls.

What’s a healthy base vs. variable mix for AEs and SDRs?

There’s no single magic ratio, but in many B2B tech environments AE plans have shifted from ~50/50 toward something closer to ~55/45 (base:variable) over the last decade, while SDR plans have moved from ~60/40 toward ~67/33. The right mix for you depends on your market, sales cycle length, and hiring dynamics, but in general you want enough variable pay to drive behavior without creating undue risk or making roles uncompetitive.

How many reps should be hitting quota?

Kyle uses a rule of thumb that roughly 65% of reps should be at or above quota in a healthy system. If far fewer are getting there, it may signal unrealistic targets, poorly defined territories, misaligned metrics, or process issues upstream. If nearly everyone is dramatically over-achieving, quotas may be too low or your plan may be underpriced relative to the value reps are creating.

What are common mistakes in sales comp design?

Some frequent missteps include: tying pay to metrics that reps don’t fully control, using too many different measures in one plan, ignoring how the plan will be operationalized in your CRM, and neglecting to stress-test scenarios (e.g., what happens if one rep has a breakout year?). Another subtle mistake is failing to align comp with the company’s real strategic objective—like emphasizing new logos when leadership actually cares more about expansion or retention.

Should sales leaders still take big equity over cash tradeoffs?

It depends on your risk tolerance and the company’s trajectory. In frothy markets, leaders often accepted sizable salary cuts in exchange for larger equity grants. After a period of lower revenue multiples, fewer exits, and dilution, many executives have become more cautious, insisting on fair market cash compensation even when equity is part of the package. Equity can still be valuable, but it’s wise to view it as upside, not a guaranteed outcome.

What’s one simple personal finance shift that can help a high-earning seller?

A straightforward move is to separate income growth from lifestyle growth. For example, commit to automatically increasing your 401(k) and after-tax investing whenever you get a raise, instead of letting every bump flow into cars, housing, or discretionary spending. That habit, combined with avoiding high-interest debt and unnecessary financing (like constantly rolling car leases), can dramatically improve your net worth over a decade.

Disclaimer

This episode and page are for educational and informational purposes only and do not constitute financial, tax, legal, or compensation consulting advice. Sales compensation structures, market benchmarks, and investment strategies can vary widely by company and individual circumstances. Always consult with qualified professionals—such as your CFO, HR/comp advisor, and financial planner—before making changes to compensation plans or personal financial strategies.

Next Steps

If you lead a revenue team or sit in the C-suite, your comp plan is one of the highest-leverage tools you have—and one of the easiest places to quietly waste millions. Block 60–90 minutes this month to review your current plans with Kyle’s lenses in mind: simplicity, alignment to strategy, quota attainability, and clear attribution. Ask honestly whether your plan drives the behavior you say you want.

When you’re ready to connect compensation design with your broader wealth and career strategy—as a sales leader, founder, or high-earning seller—explore more episodes and resources at Making Sense of Your Money, or learn how Tailored Wealth partners with revenue leaders and equity-rich professionals at yourtailoredwealth.com.