Top Performers Don’t Take Jobs, They Place Bets

Why Elite Talent in Tech Now Evaluates Employers Like Investors

Let’s get one thing straight: the best people in sales and marketing? They’re not looking for a job. They’re looking for an opportunity worth investing in.

And not just investing money—investing time, energy, network, and reputation. That’s a much higher bar. One that traditional job descriptions, career paths, and compensation packages often fail to clear.

Especially in the tech world, a quiet revolution is happening. Elite commercial leaders—those who consistently move the revenue needle, are starting to think like investors, not employees.

They size up companies the same way a VC evaluates a startup: Is the mission compelling? Is the trajectory credible? And is the leadership worth backing?"

And increasingly, they’re choosing fractional, advisory, or on-demand roles that give them more control over the upside—and more insulation from the downside.

Let’s break down this investor mindset and what it means for anyone trying to attract top-tier commercial talent.

The Shift No One’s Talking About

In theory, high performers want growth, challenge, and a great culture. That’s the story we’ve told ourselves.

In reality? Many of them have been burned.

They’ve joined promising companies only to find:

• a messy go-to-market strategy,

• uninspiring leadership,

• or a product that won’t sell no matter how good the pitch is.

So, they’ve become savvier. More sceptical. Less focused on titles or even salary—and more focused on signal. Is this company worth placing a bet on?

As First Round Capital (US based VC firm) reported in their widely cited startup talent survey, top candidates “treat interviews like diligence sessions,” often grilling founders on GTM plans, growth efficiency, and burn rate.

As one seasoned GTM operator put it to me recently:

“I’m not looking for a job—I’m looking for my next asymmetric upside.”

Top commercial talent in tech are taking a portfolio approach to career decisions

The Three Filters of the Investor Mindset

If you’re trying to hire elite sales or marketing talent, they’re likely conducting due diligence. Here's what they’re evaluating:

Mission Clarity: Do I Believe in This?

First up: what’s the point of this company? Not the tagline. The real problem you’re solving.

Top talent wants to believe in what they’re selling. They want to stand in front of a customer and feel confident the product actually makes their life better. That means:

• The founder / CEO story needs to hold weight.

• The positioning needs to be sharp.

• The value proposition needs to be clear—and different.

In the Harvard Business Review, researchers have noted that “high performers are disproportionately motivated by meaningful work,” and that mission alignment plays a huge role in retention and performance.

Trajectory: Is the Upside Real, or Just Hype?

Next: they’re looking at the trajectory.  Elite talent asks:

• How big is the market?

• What’s the go-to-market maturity?

• Are we in a race with better-funded, more disciplined competitors?

• What’s churn like?

• What are the unit economics?

This isn’t just “do I believe in the product?” It’s “do I believe this company will be worth more 18 months from now?”

Tomasz Tunguz of Redpoint Ventures has written extensively on how top-performing operators evaluate companies through the lens of growth efficiency—looking at CAC payback, retention curves, and burn multiples before they accept an offer.

Fractional leaders in particular get picky here—they’re often sitting in multiple businesses and know what good looks like. They want to attach themselves to a rocket ship, not a “zombie startup” dragging out its runway with hopeful LinkedIn posts.

Leadership Quality: Who’s Driving the Bus?

This one’s personal.

Top performers want to work with leaders they trust. Not the kind who talk a big game on stage, but the ones who can make decisions, stay focused and build trust across teams.

According to McKinsey, poor leadership and unclear strategy are two of the top reasons high performers leave an organization—even more than pay.

They’ll ask:

“Is this someone who will listen to customers? Will they back the GTM team when the product is behind? Will they back me?”

And they’ll trust their gut. If the leadership team is ego-driven, dysfunctional, or checked out, they’ll pass. No matter how good the comp.

Why Fractional & On-Demand Is the Smarter Play

You might be thinking: “If they’re that good, why wouldn’t they just take a great full-time role?”

Because more and more of them are choosing portfolio careers—just like investors diversify risk, they do the same with their careers.

Fractional or advisory roles allow them to:

• Work with multiple companies at once

• Test for fit before going all-in

• Independent players can earn meaningful advisor equity without a 60-hour workweek (applies to independent operators)

• Avoid the politics and inertia that often come with full-time roles

According to TechCrunch, the demand for fractional executives and “on-demand operators” has surged in the last few years—particularly in early-stage and growth-stage tech companies seeking experienced GTM help without committing to full-time costs.

This isn’t a side hustle anymore—it’s a smarter business model for top performers.

What This Means for Founders & GTM Leaders

If you’re building a team or trying to attract a proven commercial leader, it’s time to flip the script.

Stop hiring. Start pitching.

• You’re not offering a job—you’re offering an investment opportunity. Elite talent wants mission clarity, credible traction, and leadership they can trust. Skip the perks and sell the vision, momentum, and who’s driving it.

You could even borrow from the investor playbook:

• Create a one-pager that outlines the company’s strategic plan

• Share your Vision Memo and founder values

• Be transparent about the challenges—not just the opportunity

The Future Is Portfolio-Driven

The best minds in GTM today don’t see their careers as a ladder—they see it as a portfolio of bets.

They’ll double down when they believe in the upside.

But they won’t do it for a ping-pong table, a VP title, or a vague promise of stock options.

If you want to earn their time, and their impact, you need to make the opportunity investable.

So, the next time you're looking to hire a head of sales, a marketing leader, or a GTM advisor, don’t think: “How do I convince them to take the job?”

Think “Would they invest in this company, if their currency was time, energy, and reputation?”

Because that’s exactly what they’re doing.