Your Next Job Is a Wealth Decision | Anthony Herrera with Dan Pascone | Ep #63

Written By: Dan PasconeJune 12, 2026

Answer Box (TL;DR)

TL;DR: For a high-earning executive or go-to-market leader, a career move is not just a career decision. It is a financial planning decision. Anthony Herrera, president of Pursuit Sales Solutions, joins Dan Pascone to break down what the GTM job market looks like right now, why the equity dangled in a comp package is often a pipe dream at the two-to-three year average CRO tenure, what smart candidates negotiate beyond base and bonus, and why the mega backdoor Roth provision in your next employer's 401k plan could be one of the most underrated financial levers in a high earner's prime earning years.

Key Takeaways

Your next career move is a financial planning decision. How you negotiate the comp package, whether the equity timeline is realistic given the average two-to-three year CRO tenure, and whether the 401k offers a mega backdoor Roth option are all decisions that quietly shape how fast you reach work-optional status.
Equity with a five-year earnout is not part of your comp package when you are in a role with a two-to-three year average tenure. It is a lottery ticket. The practical move is to negotiate more of that value into base or bonus where you can actually count on it.
The mega backdoor Roth is one of the most underrated planning levers available to high earners in prime earning years. If your employer offers an after-tax 401k contribution with automatic conversion to Roth, and you can fully fund it, you are building a tax-free retirement bucket that compounds for decades and gives you significantly more flexibility in distribution when stable income stops.
Deferred compensation is an increasingly relevant negotiating tool for executives in their 40s and 50s who have a clear exit timeline from corporate. Deferring income to a lower-income year, whether that is early hybrid retirement or a transition period, can produce meaningful tax savings and is worth explicitly raising in negotiations for senior roles.
The phased exit negotiation strategy, three years full-time building followed by two years fractional or advisory, is a win for both sides. The executive gets a structured transition to hybrid retirement. The company gets built-in succession planning instead of starting over when the leader leaves.
GTM talent in medical sales, general B2B, and skilled trades backed by private equity is becoming increasingly competitive with tech for compensation. If you are a tech revenue leader, you are no longer competing only within your sector. Medical firms are actively recruiting for your skill set and paying to get it.

Key Moments

[00:00] Dan opens: for a high earner in a GTM or executive role, the next career move is a financial planning decision, not just a career decision
[01:42] Anthony Herrera welcomed: president of Pursuit Sales Solutions, 20 years matching elite go-to-market talent with growing companies nationwide
[04:52] What makes GTM hiring unique: builders, scalers, and sustainers are three distinct profiles that require completely different candidate matching
[09:23] Advice for executives trying to avoid the two-to-three year CRO tenure trap: understand the environment before accepting and negotiate equity timelines that reflect realistic tenure
[11:36] How to figure out which GTM niche you are best suited for without taking a series of bad fits: assessments like the Predictive Index and intentional networking outside your current org
[15:13] GTM compensation trends in 2026: medical sales stable and competing aggressively for tech talent; B2B and skilled trades backed by PE infusing GTM leadership; tech still aggressive on base, bonus, and equity
[19:58] What to negotiate beyond base, bonus, and equity: professional development stipends, remote and hybrid flexibility, runway to hire and build a team in writing
[23:00] Dan introduces the mega backdoor Roth: the third 401k bucket most high earners never ask about, and why it can be a game changer for tax-efficient retirement building in prime earning years
[27:00] Deferred compensation as a senior executive negotiating tool: deferring income to a lower-income year aligns with hybrid retirement planning and is worth raising explicitly in negotiations
[29:00] The phased exit negotiation: three years full-time building, two years fractional or advisory, framed as succession planning for the employer
[31:13] Lightning round: fajitas, ChatGPT, lifting four days a week, a mission trip to Uganda with his son, and "keep saying yes"

Episode Summary

Most executives treat a job change as a career decision. Dan Pascone and Anthony Herrera make the case that for any high earner in a go-to-market or executive role, it is equally a financial planning decision. The comp package you negotiate, the equity structure you accept, and the retirement benefits you ask about will shape your work-optional timeline in ways that compounding income alone cannot fix later.

Anthony Herrera is president of Pursuit Sales Solutions, a recruiting firm that has completed over 1,400 searches in 2025 across tech, medical sales, general B2B, and skilled trades. His observation on the market is direct: the supply of elite go-to-market talent is not matching demand, and multiple industries are now competing for the same people. Medical firms are recruiting tech revenue leaders for their AI fluency. Private equity-backed skilled trades companies are bringing in GTM executives from growth technology. If you are a tech-trained revenue leader, you have more options and more leverage than the job market makes visible.

The conversation covers the structural problems with how GTM leaders evaluate comp packages. The average CRO or VP of Sales tenure sits between two and three years. Equity with a five-year earnout is not a compensation item in that context. It is a lottery ticket. Anthony advises senior candidates to negotiate that value into base or performance-based bonus structures they can actually count on, and to get the runway to hire and build in writing before accepting.

Dan adds two financial planning dimensions that rarely come up in recruiting conversations but matter enormously for executives in their prime earning years. The first is the mega backdoor Roth: an after-tax 401k contribution with automatic conversion to Roth that, when fully funded over five to ten years, builds a significant tax-free retirement bucket. The second is deferred compensation, which is worth raising explicitly in senior executive negotiations for anyone who has a clear timeline for leaving corporate and wants to shift income to a lower-tax year during a transition period.

The episode closes with a specific negotiating framework Anthony calls the phased exit: three years of full-time leadership followed by two years of fractional or advisory work, presented to the employer as a succession planning structure rather than a departure plan. It is a win for both sides and an underused tool for executives who have one or two more corporate stops before hybrid retirement.

What Smart GTM Executives Negotiate in 2026

Comp Structure

Base, bonus, and equity aligned to realistic tenure. If the equity earnout requires five years in a role with a two-to-three year average tenure, negotiate that value into base or a performance-based bonus instead.

Retirement Benefits

401k with Roth option as baseline. Ask specifically whether the plan offers an after-tax contribution bucket with automatic Roth conversion, the mega backdoor Roth. Increasingly available across firm sizes, and one of the highest-leverage tax planning tools for high earners in prime earning years.

Professional Development

A dedicated development budget, $10,000 to $20,000 per year, for conferences, memberships, and coaching outside of team-focused events. Increasingly common and worth asking for explicitly.

Hiring Runway in Writing

A written commitment from ownership or the C-suite on the headcount budget and green light to hire and build for at least the next two years. Executives who do not get this in writing often find themselves as individual contributors in a role they accepted to lead a team.

Deferred Compensation (Senior Roles)

For executives in their 40s and 50s with a clear exit timeline from corporate, negotiating deferred comp to a lower-income year is worth raising explicitly. The tax benefit of aligning high comp years with distribution in a lower-income period can be significant.

The Phased Exit Framework

Three years full-time building followed by two years fractional or advisory, framed to the employer as succession planning. A win for both sides: the executive gets a structured transition to hybrid retirement, the company avoids starting over when the leader eventually departs.

Transcript

Dan Pascone (00:00): Hey, I'm Dan Pascone, CEO of Tailored Wealth and host of the Making Sense of Your Money podcast, where every conversation is built around one idea. Your money is a tool to design and live your version of a rich life. So if you're a high earner in a go-to-market or executive role, your next career move isn't just a career decision. It's a financial planning decision. How you negotiate your comp package, whether your 401k offers a mega backdoor Roth, whether equity you're being dangled is realistic or just a pipe dream, these are the decisions that quietly shape how fast you reach your work-optional potential. So today I'm joined by Anthony Herrera, who's president of Pursuit Sales Solutions, a recruiting firm that specializes in matching elite go-to-market talent with growing companies across the country. We're digging into what the GTM job market actually looks like right now, how to negotiate a comp package that actually reflects your full financial picture, and what smart leaders think about before they take on the next role.

Anthony Herrera (02:33): For the last 20 years of my career, I've been involved in either recruiting, developing or retaining top talent for organizations. Right now I'm at Pursuit. Pursuit is a recruiting firm that specializes in go-to-market talent. In one sentence: we match elite go-to-market talent with growing and scaling companies, and we do that nationwide.

Anthony Herrera (04:52): What's unique about GTM hiring is that each situation is unique. You can grow in your career and be very specialized in early stage building from the ground up. There's no infrastructure, there's no playbooks. And you can be very successful having a career like that. On the flip side, you can take somebody who is great at taking something that's maybe established and squeezing more juice out of it. And then you can have somebody who can take something that's gone the wrong direction and rebuild it. Those are three distinct profiles. Clients sometimes need to know what category they fall in and what type of person they need.

Anthony Herrera (09:23): Really understand what is the environment you're going into. If it's an early stage company and all the sales have been driven by the founder, they probably don't have a playbook, they don't even have a CRM. So if you're going into that, you need to know that there's high risk, potential for high upside, but there's more risk. How do you negotiate your comp package? If you have an equity earnout that doesn't kick in for three to five years, but yet we know the average tenure is two to three years, that's not part of your comp package. That's a pipe dream. How can you move that more into the base or how can you move that more into bonus? Because that's gonna help you get some ground on that.

Dan Pascone (23:00 approx.): I want to add a couple of pieces that I think folks should be taking a look at above and beyond just comp: retirement package and retirement benefits. The equity component is always a bit of a lottery ticket in that discussion, depending on how it's structured. If you're with a bigger firm and they're giving you RSUs, that's a little bit easier. If you're with a smaller private firm and you're getting options, that is very much a lottery ticket. But a couple of things you can count on would be 401k and 401k match. Here's the one I'm curious if you come across this at all. There are three components to the 401k: the traditional 401k which is your pre-tax money, the Roth 401k, and then the third component is the after-tax bucket and the ability to auto-convert from after-tax to Roth, which is the concept we refer to as the mega backdoor Roth. If your company offers that, it can be a real game changer for a leader in their prime earning years who is really geared toward a tax-efficient retirement. If you're able to put that strategy to work for call it five to ten years, you're building up a Roth bucket that grows tax-free and that you can access tax-free in retirement. You get a lot more flexibility with how you're able to draw from your savings when you don't have a stable income coming in.

Dan Pascone (28:00 approx.): Deferred compensation. There can be some benefits to both the company and to the employee by utilizing deferred compensation, especially if you have a pretty good idea of what your exit from corporate looks like and when. Because deferring comp to a timeframe when your income is lower is really, really unique from a tax perspective and has a bunch of other benefits from a financial planning perspective. Are you seeing deferred comp being worked into offers with the CRO, the CMO, the VP level function?

Anthony Herrera (29:00 approx.): I don't want to say it's a widespread theme, but you are seeing it, especially in more established industries where they want the seniority and the experience. So they're getting these forty-plus year olds, fifty-plus year olds. And so that is becoming a factor and they know it is part of the negotiation. You're also seeing what I would call a phase-out. You not only have one component which is the deferred compensation, the other component is, hey, we want to sign you on a contract for these three years, and then we'd like to phase you into a more fractional role, an advisory role, and start to draw down your salary. Those are unique. It's not like this is a theme going on widely, but you see that as a negotiating tool. I always tell people, hey, that is an option.

Anthony Herrera (30:26): I love this for senior employees because if you know, hey, I have one more stop and in that stop I'm more defined, I've got five more years, you go to an organization and you say, look, I can give you five years, three of them full time. I'll build this out for you. And then I will train and develop on a fractional or advisory capacity for two more years. So the organization, talk about the win-win. It's succession planning. And that's where more organizations are starting to think about that idea of succession planning, especially the more traditional industries. They don't want to sign this person for three years, get a big win, and then three years later they're gone and the ship's having to get rebuilt. So I tell senior talent, don't be shy to put that on the table.

Dan Pascone (34:15): That's it for the episode. You can find our podcast along with our newsletter and YouTube channel all for free at makingsenseofyourmoney.com. And as always, don't forget to live your version of a rich life.

Resources and Citations

FAQ

Why is a GTM career move a financial planning decision, not just a career decision?

For any high earner in a go-to-market or executive role, how you negotiate the comp package, whether the equity timeline is realistic given the role's average tenure, whether the employer offers a mega backdoor Roth in their 401k plan, and whether deferred compensation is available all shape how quickly you reach work-optional status. These are not HR questions. They are financial planning decisions that affect your tax situation, your retirement account balances, and your transition runway for years after the offer is signed. Consult a qualified financial planner before accepting any offer that significantly changes your income, equity, or benefits structure.

Why is equity with a five-year earnout not really part of a CRO comp package?

The average tenure for a CRO or VP of Sales sits between two and three years. An equity earnout with a five-year cliff or vesting schedule is statistically unlikely to be realized in a role with that average tenure. Anthony Herrera describes this directly: it is a pipe dream, not a compensation item. The practical negotiating move is to get as much of that value as possible into base salary or a performance-based bonus structure that pays out within a realistic timeframe. For executives who do receive equity, especially in private companies, the structure, vesting schedule, and likelihood of a liquidity event should all be evaluated carefully. Consult a qualified financial planner and tax professional before making decisions around equity compensation. All equity investments involve risk.

What is the mega backdoor Roth and why does it matter for high earners?

The mega backdoor Roth is a strategy that uses a third bucket inside a 401k plan: after-tax contributions that are then automatically converted to a Roth account. Unlike standard Roth 401k contributions, which have the same annual limit as traditional pre-tax contributions, the after-tax bucket can be funded up to the total 401k plan limit minus employer and employee pre-tax contributions, allowing significantly higher Roth balances over time. For a high earner in their prime earning years who cannot contribute directly to a Roth IRA due to income limits, this can be one of the highest-leverage tax planning tools available. The Roth bucket grows tax free and is accessed tax free in retirement, providing flexibility in distribution when stable income stops. Not all employer plans offer this feature. Consult your plan administrator and a qualified financial planner to determine whether your current or prospective employer's plan supports after-tax contributions with in-plan Roth conversion. Contribution limits are subject to IRS rules and may change annually.

How should senior executives use deferred compensation as a negotiating tool?

Deferred compensation allows an executive to defer earned income to a future tax year, typically a lower-income period such as the year after leaving full-time corporate work or during a hybrid retirement transition. For an executive in their 40s or 50s who has a clear timeline for stepping back from corporate, this can produce meaningful tax savings by shifting high-income-year compensation to a year when their marginal rate is lower. Anthony Herrera notes that while this is not a widespread trend across all industries, it is increasingly appearing in negotiations for senior executive roles in more established sectors. It is worth raising explicitly, even if the employer has not proactively offered it. Consult a qualified financial planner and tax professional before structuring any deferred compensation arrangement, as the rules are complex and errors can result in significant tax penalties.

What is the phased exit negotiation strategy and who is it right for?

The phased exit strategy involves proposing a multi-year engagement structure to a prospective employer: typically three years of full-time leadership building or rebuilding the GTM function, followed by two years of fractional or advisory work at a reduced commitment level. Framed to the employer as succession planning rather than a departure plan, it addresses one of the most common organizational pain points in senior GTM hiring: the leader who builds something significant and then leaves, forcing the company to start over. For executives who have one or two more corporate stops before hybrid retirement and know roughly what their timeline looks like, this structure can accelerate the transition to more flexible, purpose-driven work while providing the employer with continuity. Consult a qualified financial planner to evaluate whether this structure aligns with your hybrid retirement timeline and income planning needs.

What should GTM leaders look for in a comp package beyond base, bonus, and equity?

Anthony Herrera identifies several high-value but often overlooked comp components. A professional development budget of $10,000 to $20,000 per year for conferences, memberships, and personal coaching outside of team-required events is increasingly available and worth negotiating. A written commitment from ownership or the CEO on the headcount budget and green light to hire for at least two years protects against the common scenario where a leader is hired to build a team but is never actually allowed to. Remote and hybrid flexibility for leadership roles remains negotiable, especially in tech, and should be addressed explicitly before accepting. Dan Pascone adds retirement benefit quality, specifically whether the plan offers a mega backdoor Roth, as a compensation consideration that most high earners never ask about and that can significantly affect long-term financial outcomes. Consult a qualified financial planner to evaluate the full value of any compensation package before signing.