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The GTM Shift: Leveling Up Leadership in a Tight Market

by Eric Walczykowski​, Tess Fischer

November 20, 2025,,,,

In our latest episode of Tailored Talent, I spoke with Tess Fischer, Partner and Head of our Go-To-Market Leadership Practice, about what may be one of the most complex and competitive talent markets we have seen in years.

Her team has been remarkably consistent, showing steady growth year after year, because go-to-market leadership remains at the heart of every value creation story in private equity. Yet, the dynamics are shifting fast.

Watch the full conversation with Tess Fischer on Tailored Talent.

SLIDE 1 - Intro - for event page use only
Watch the episode

Leveling Up Ahead of Exits

As Tess pointed out, many portfolio companies are entering the final stretch before an exit. The CRO or CMO hired 18 months ago to drive a turnaround may not be the same leader who can sit across from buyers and sell the company story.

Sponsors are re-evaluating their leadership benches. They are asking: Who do we need around the table to maximize value in the next 12 to 18 months? That question has led to a wave of “leveling up,” seeking leaders who can not only execute but credibly represent the business through a sale process.

The Tightest Market Yet

But replacing or upgrading those leaders is not simple. The market for proven go-to-market executives is tighter than ever.

Tess described two major forces driving the squeeze. First, top candidates are staying put. Many see exits on their horizon and want to realize those outcomes before considering a move. Second, private equity firms have become more conservative in what they want: leaders who have seen the movie before. They must know the ICP, understand private equity, have scaled in the same market, and ideally be local.

That combination has significantly narrowed the pool. Tess shared that step-up hires, meaning executives taking their first top seat, are down 5% over the past year. The market’s tolerance for risk has shrunk.

Navigating Scarcity with Speed and Precision

When demand is surging and supply is constrained, timing becomes everything.

As Tess explained, success now depends on knowing when great executives will become available. Her team tracks exit timelines across the market, anticipating when talent may be ready to move. That intelligence allows Bespoke to move quickly, often completing searches in just over a month.

Our Executive Index, which now includes more than 700,000 software executives across the U.S., provides a top-down view of the market that few others can match. It ensures every possibility is accounted for, from the known network to the overlooked high-performing operators who might not yet be on anyone’s radar.

Shifting Structures and Rising Compensation

Another clear trend Tess highlighted is structural. Go-to-market leadership, once consolidated under CROs or Presidents, is now being distributed. Firms are hiring dedicated Chief Sales Officers, Chief Marketing Officers, and Chief Customer Officers. It is a move toward sharper accountability and cross-functional collaboration, with each leader focused on their lane and running at full speed toward shared outcomes.

And compensation is still rising. Tess noted that despite every sponsor’s wish for moderation, offers continue to climb. We are seeing sign-on bonuses, retention packages, and guarantees designed to win the right leader. In one recent case, that meant a million-dollar cash offer for a CRO, a reflection of both scarcity and value creation potential.

In a market this tight, firms cannot afford to guess.

They need visibility across the talent landscape, the precision to target the right executives, and the credibility to close them quickly.

As Tess put it, “Everyone wants the unicorn, but the best teams are one putt away on the scorecard.”

It is a perfect metaphor for today’s environment. Success comes from preparation, discipline, and an expert partner who knows how to read the green.

To learn more about Go-to-Market leadership trends subscribe to the Tailored Talent podcast or connect with the GTM executive search team at Bespoke Partners.

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SLIDE 1 - Intro - for event page use only
Watch the episode

Authored by:

  • Eric
    Chief Executive Officer

    Eric is passionate about building high-performing teams that value doing their best, working together, overcoming adversity and learning.

    As a proven growth executive, Eric has served as CEO, President, Board Member, Investor and Advisor for technology companies that achieved over $4.5B in successful exits.

    Eric brings to Bespoke Partners significant professional services experience from Deloitte and Andersen, as well as the high-growth client executive perspective for private equity-backed technology companies.

    Eric earned an MBA from the Kellogg School of Management at Northwestern University and a BS in Business from Fresno State University.

  • Partner, Go-to-Market Practice Lead

    Tess brings over 19 years of experience building and managing networks, clients and teams in private equity executive recruiting and human capital management. She has worked in and around private equity her entire career and is driven by an interest in people, organizations and the desire to build relationships that deliver results.

    In her prior role as a Partner at Morgan Samuels, Tess led the firm’s Software and Tech-enabled Services practice. She worked closely with private equity funds and their portfolio companies to hire c-suite executive talent. Previously, Tess was Senior Executive Recruiter at Vista Consulting Group where she placed over 30 executives across Vista Equity Partners portfolio of SaaS companies every year. In her early career, Tess helped grow Gerson Lehrman Group’s Austin office and was Vice President of Network Development where she and her team recruited experts to assist the research strategies of leading hedge funds and private equity funds.

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