How GTM Leaders Can Work With Recruiters and Negotiate Comp | Dan Pascone with Dane Crossie | Ep #72

Dane has just passed 23 years in headhunting. More than half of that time has been spent on go-to-market search for data and intelligence companies in the UK and the US, and along the way he has done a lot of career coaching for GTM professionals, from positioning and job searching to interview prep.

He recently founded Alpha Source GTM, a specialist GTM headhunting firm for data, intelligence, and research companies in the US and UK. His clients sell things like alternative data, financial markets data, and consumer insights, mostly to financial institutions and corporates. Roughly 75% to 80% of his placements are sales and sales leadership roles, with the rest in marketing and product, from senior individual contributors up to VP and C-level, at companies ranging from Series A to C through established enterprises.

Dane says starting his own business was an itch he wanted to scratch for a long time. He worked his way up to director-level roles, learned from mentors he's grateful for, and came close to making the leap more than once. There was always a reason not to: kids, travel, family, and a couple of international moves.

What finally got him across the line was regret. He didn't want to approach retirement age and look back thinking he should have done it. Once he made the move, he found it wasn't as scary as he expected, even if it's still daunting and challenging. That idea of avoiding regret is one we hear constantly from the executives we work with. If you're weighing a similar move, our guide on how to navigate a career change without losing financial ground covers the money side.

Dan, a former sales leader himself, raised a pattern he hears constantly in GTM networks: revenue-focused leadership roles have some of the highest turnover in business. Dane points to many variables, since recruiting is people working with people, and both candidates and companies change over time. As he puts it, he sometimes wishes he were selling chairs, because a chair won't change its mind.

The bigger factor, in his view, is soft skills. For technical roles like software engineering, a recruiter can check tangible experience with a technology, and that can rule someone in or out about 80% of the way. For sales and GTM roles it's almost the reverse. So much of the job depends on soft skills and personality, which show up with customers and inside the business, and those are hard to assess until someone is actually in the seat. Sales methodologies are making it easier to test, but it remains the hardest variable to judge in an interview process. For more on the planning side of these careers, see our post on financial planning for go-to-market leaders and sales professionals.

Dane first piece of advice is to work with specialists. A decade and a half ago, generalist recruitment firms handled everything from procurement to sales to technology. Companies now want specialists, and he says candidates should look for the same thing:

• Specialize on both axes: Look for recruiters who specialize in your role type and in the industry and kinds of companies you want to work for.

• Use search and referrals: Simple keyword searches on LinkedIn work, and referrals are worth their weight in gold, because people don't refer someone who didn't do a good job for them.

• Go deep with 2 or 3: Pick a small number of strong specialists and invest real time helping them understand your background and what you want next. That's usually all you need.

• Treat it as a two-way street: Keep in touch and update them when something in your world changes, so you stay top of mind.

• Ask for proactive help: Share the companies you'd like to work for and ask whether they have relationships there. Good recruiters will approach those companies on your behalf and help open doors.

About 40% of Dane recent work has been in the US, mostly on the East Coast. He says salaries there have risen much faster over the last 10 years than in the decade before, enough that some UK companies flinch at East Coast numbers. That upward trend is putting more pressure on hiring decisions: hiring managers have to get sign-off from boards or investors, so the process has to get the hire right.

Candidates, meanwhile, are looking at the full picture. It used to be base and on-target earnings (OTE). Now, with more Series A to C companies and private equity investment, it's what surrounds those numbers, including healthcare in the US and, above all, equity. Senior GTM leaders are looking for the exit and for real skin in the game, and a comprehensive package is often what tips the balance. Dan agreed: in our work, equity is often more important than base or the variable comp structure, because base and variable tend to be similar from company to company while equity can differ enormously. Our guide to equity compensation explained walks through how those packages work.

Dane is seeing packages become more complex, with sliding scales tied to growth and to hitting stretch goals, not just the plan:

• Accelerators on variable comp: Once attainment passes 100%, say at 110% and above, the percentage paid on variable comp goes up.
• Equity rewards for overachievement: A similar idea is creeping into equity, with additional grants for beating the company's growth goal by a set percentage.
• More links to profit: Some of these incentives are tied to profit, not just revenue.

Dan sees the profit link as healthy. The aim is revenue that actually improves the bottom line, not revenue for its own sake. Late in his corporate career, he tried to think more like a business owner, and that mindset helped him when he went out on his own. When comp plans bake it in, they reward the right behavior.

Dane traces much of the gap to the post-COVID hiring frenzy. Competition for strong senior ICs and leaders was fierce, companies threw big numbers at candidates, and average salaries skyrocketed, much more steeply in the US than in the UK. He's not sure exactly what drove the difference, whether it was more competition or faster company growth.

Then, around the end of 2022 and early 2023, interest rates went up and companies stopped hiring. Many people were left on big, inflated bases, but because targets were set so high to match those salaries, they struggled to hit their variable comp and weren't actually earning more than in the role they had left.

Dan asked the question many leaders wrestle with: how do you top out your comp without frustrating the employer you're about to join? Dane says it starts at the very beginning of the process, not at the offer stage:

• Strategize with a trusted recruiter: A recruiter you have a real partnership with will know how that specific company tends to negotiate, so you can be honest and plan together. There's no single pathway, because every company approaches it differently.
• Lead with the problem you solve: Set the money aside for a moment. Where is the business today (point A), and where does it want to go (point B)? Can you get them there?
• Become the vehicle: If you position yourself as the answer to their problem, the negotiation begins before you ever talk about comp, and you'll be in the strongest possible position when you do.

Dan used to give similar advice in his corporate career. Connect what you're asking for to the outcomes the company wants. As a business owner, you look at a hire as an investment, and if it has a high probability of a strong return, you're willing to invest more.

• 1 meal for the rest of your life: Steak.
• A tool he can't live without: A Nintendo Switch. Playing the Disney games with his 2 daughters is some of the best connection time he has. Dan noted it's the first time a guest has picked a video game.
• A habit behind his success: Connecting with people genuinely. Being trustworthy and dependable, and doing what you say you're going to do, has gotten him further than anything else.
• Bucket list: He has traveled to more countries than he can count since his mid 20s. Still to check off: taking his family on a private jet, even just a short trip to Europe.
• Advice to his younger self: You don't have to have it all figured out, and you may never feel like you do. Keep your eyes open and take it 1 step at a time.
• His version of a rich life: Balance. He loves his work and wants the business to do well, but not at the expense of time with his wife and daughters, and the ability to give them experiences they might not otherwise have. Dan added that balance looks different for everyone; the key is being intentional about it.

Two things stand out. First, a bigger base isn't the same as a better package. Dane's post-COVID story shows how an inflated base paired with an unreachable target can leave someone earning less than the job they left. The variable, the accelerators, the equity terms, and how attainable the plan really is all matter as much as the headline number.

Second, the comp negotiation starts with positioning, not with numbers. The leaders who get paid the most are usually the ones the company sees as the answer to a specific problem. For high earners, the planning work follows the same logic: before you accept, model what the package is actually likely to pay, and how the equity piece fits your timeline and taxes.

All figures below are assumed and for illustration only.

• Current role: $250,000 base and $250,000 variable at target, with attainment around 100%, for about $500,000 a year.
• New offer: $300,000 base and $300,000 variable at target, a $600,000 OTE.
• If attainment lands at 60%: Variable pays $180,000, so total cash comp is $480,000, about $20,000 less than the current role despite a $100,000 higher OTE.
• If attainment reaches 110% with a 1.5x accelerator on the overage: The extra 10% of target ($30,000) pays $45,000, for $345,000 in variable and $645,000 in total.

The gap between those outcomes is why we encourage clients to build their core lifestyle around base pay, treat variable comp and equity as goal funding rather than fixed income, and pressure-test how realistic a target is before signing. This example is hypothetical and is not a prediction or guarantee of results.

At Tailored Wealth, complex compensation is our home turf: base, bonus, variable comp with accelerators, RSUs, options, and deferred comp. Before you accept an offer, we help you model what each package is realistically likely to pay, what the equity could mean under different outcomes, and how the tax picture shifts. Our Equity Compensation Playbook, our structured rules for RSUs, options, ESPPs, and deferred comp, guides how to handle grants once they vest.

We also fold those decisions into Life-Driven Planning, our 6-phase process covering Cash Flow, Retirement & Hybrid Retirement, Risk, Expense & Goal, Tax, and Legacy, so a career move supports the life you're building rather than just the next title. We don't endorse or evaluate the guest's business or services.

This is written for sales, marketing, and revenue leaders and other corporate executives in their 40s and 50s, with household income of $500,000 or more and complex comp like variable pay, accelerators, and equity, who are weighing a move or negotiating a new package and want to understand what it's really worth before they sign.

If you're weighing a new role, negotiating a package, or trying to figure out what your variable comp and equity are really worth, book a Free Wealth Strategy Call. It's a low-friction conversation about your plan, not a sales pitch.