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

Most executives evaluate a job change the way they'd evaluate a career opportunity: title, scope, culture, maybe the headline comp number. Anthony Herrera, president of Pursuit Sales Solutions, has run over 1,400 go-to-market searches in 2025 alone across tech, medical sales, general B2B, and skilled trades, and his read on the market is direct: the supply of elite go-to-market talent isn't matching demand, and industries that never used to compete for the same people, tech, medical sales, private equity-backed skilled trades, now are.

That gives senior candidates more leverage than the job search makes visible. But leverage only helps if you know what to negotiate. Comp package, equity structure, and retirement benefits all shape your work-optional timeline in ways that are much harder to fix after you've signed than before.

Base, bonus, and equity aligned to realistic tenure. If the equity earnout requires five years in a role where the average tenure is two to three years, negotiate that value into base or a performance-based bonus instead. See our full breakdown in Upgrade Your Pay: How to Get the Best Compensation Package.

A 401(k) with a Roth option is baseline. Ask specifically whether the plan offers an after-tax contribution bucket with automatic Roth conversion, the mega backdoor Roth. It's increasingly available across firm sizes and is one of the highest-leverage tax planning tools available to a high earner in their prime earning years. We cover the mechanics and current limits in Mega Backdoor Roth 2026: How to Use Your 401(k) Limit.

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

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

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; see how the timing works on the way out in How Is Deferred Compensation Taxed?

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, and the company avoids starting over when the leader eventually departs.

The mistake isn't failing to negotiate salary. Most executives negotiate salary just fine. The mistake is treating everything else, retirement plan design, deferred comp, the realistic odds of an equity earnout actually paying out, as fixed terms rather than negotiable ones. Recruiters and HR aren't going to volunteer whether the 401(k) supports a mega backdoor Roth, and they're not going to flag that your equity vests on a timeline that outlasts the average tenure for your role. That's not because anyone's hiding anything. It's just not their job to think about your tax-efficient retirement bucket. It's yours, and it has to happen before you sign, not after.

Take Marcus, 47, a VP of Sales evaluating an offer from a growth-stage company. The headline number looks strong: $280,000 base, a target bonus of $140,000, and an equity grant valued at roughly $600,000 vesting over five years. On paper, that's a $1 million-plus package.

But the average tenure for his role at similarly staged companies is two to three years, and the equity doesn't meaningfully vest until year three. Treating that $600,000 as real compensation would be a mistake. In negotiation, Marcus pushes to convert a portion of the back-loaded equity into a larger year-one and year-two cash bonus instead, something he can actually count on. He also asks two questions nobody on the hiring side expected: does the 401(k) plan support after-tax contributions with an in-plan Roth conversion, and is there flexibility to structure part of his comp as deferred compensation payable in a lower-income year down the road. The answers to those two questions end up shaping his long-term tax picture more than the headline number on the offer letter did.

This is written for the high-earning go-to-market or corporate executive evaluating a new role, a promotion, or an offer from a growing company, who wants to make sure the decision holds up financially, not just professionally. If you're negotiating anything beyond base salary right now, or about to, this is the moment to widen the conversation.

If you're evaluating a new role, a promotion, or an offer right now and want a second set of eyes on the comp structure, the equity, and the retirement benefits, that's exactly what a Free Wealth Strategy Call with the Tailored Wealth team is for.