Tailored Talent

Most CEOs stepping into a PE-backed role for the first time underestimate how much of the job is about alignment before the work begins.  The deal model, the sponsor relationship, the board you build around yourself. Getting that right before the company is running is what separates a smooth hold from one that becomes a constant negotiation.  In Part 1 of this Tailored Talent conversation, Bespoke Partners CEO Eric Walczykowski sits down with Patrick Dennis, CEO of Avaya, former CEO of Venafi and a multi-exit software operator, to talk through how he approaches a new PE-backed role from the moment he says yes.  

Topics include: 

• Why the deal model is true north and what it means if a sponsor will not share it 
• How to pressure-test the deal thesis before day one through outside-in research 
• The three dimensions of push and pull: financial, operational, and governance 
• Why clear boundary conditions on executive hiring matter more than most CEOs realize 
• The case for smaller, faster boards in PE-backed software 
• How to match independent directors to the highest-complexity elements of the value creation plan  

Watch Part 1: https://www.linkedin.com/events/7442188475292102657?viewAsMember=true 

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

Why the Go-to-Market Number Two Is the Most Important Hire in PE-Backed Software | Tailored Talent with Liz Moses

The proven CRO is harder to find than ever. Experienced go-to-market leaders are leaving full-time seats for operating partner roles and board positions. PE-backed software companies are running searches into a tighter talent pool than at any point in recent memory.  So how do the best firms adapt?  

In this episode of Tailored Talent, Bespoke Partners CEO Eric Walczykowski sits down with Liz Moses, Partner in our Go-to-Market practice, to get into what is driving the supply crunch, how the CRO role is evolving, and what a disciplined go-to-market placement process looks like when the old playbook no longer applies.  

Topics covered: 

- Why PE-backed software is hiring more product-leaning CEOs and what that means for the go-to-market function 

- How the experienced CRO talent pool has contracted and where those leaders are going instead 

- Why roughly 50 percent of Bespoke's go-to-market C-suite placements are first-time executives and why that is a deliberate strategy 

- The data: searches open to a step-up executive close in approximately 93 days; searches holding out for a proven name stretch to 120 

- How revenue operations infrastructure and go-to-market operating partners reduce first-timer placement risk 

- The shift from new logo growth to NRR and GRR as the primary go-to-market performance lens 

- Where the CSO and CCO split is emerging and at what ARR threshold it starts to make sense 

- What PE boards are looking for in go-to-market leaders in 2026  

Tailored Talent is the Bespoke Partners vodcast featuring candid conversations on the talent decisions shaping PE-backed software and technology companies. 

Bespoke Partners is the leading executive search firm for PE-backed software and SaaS companies, with functional specialization across CEO and Board, Go-to-Market, Product and Technology, Finance, and HR and People practices.  

Learn more: https://www.bespokepartners.com  

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

What makes a CEO say yes today—and what makes them walk away? 

CEO Eric Walczykowski joins Katherine Baker, Lead of Bespoke Partners’ CEO, Board, and P&L Practice, to explore how CEOs are thinking about timing, market conditions, compensation, and equity through the lens of both professional ambition and personal life stage. 

With demand rising and supply tightening into 2026, this episode breaks down how sponsors and boards can align with CEOs who are choosing fewer, higher-conviction moments to charge the hill.

Watch the episode here

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

In Part 2 of this year in review, Eric Walczykowski, CEO of Bespoke Partners, is joined by Adam Boone, Chief Commercial Officer, to examine what the 2025 results made unmistakably clear. As executive turnover dropped by roughly 50 percent across private equity backed software companies, the leadership market tightened even further, raising the stakes of every hiring decision.

This discussion breaks down how leadership gaps translate into real EBITDA leakage and lost enterprise value, why executive roles increasingly represent billion dollar decisions at exit, and how delays in filling critical seats compound risk. Drawing on data from hundreds of placements and proprietary market analysis, Eric and Adam explain why executive search has become a capital allocation decision and what sponsors must understand as deal activity accelerates into 2026.

Learn more about Bespoke Partners and leadership strategy for private equity backed software companies: https://www.bespokepartners.com 

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

In this discussion, Eric Walczykowski, CEO of Bespoke Partners, and Adam Boone, Chief Commercial Officer, break down what the executive talent market revealed in 2025. They cover why executive search demand accelerated earlier than expected, how Bespoke outpaced the broader industry, and why leadership talent has become the defining lever in private equity value creation.

The conversation also explores why traditional bottom up executive search models struggle to deliver results, how top down market mapping drives completion rates above 99 percent, and why speed to close now directly impacts EBITDA and execution risk. Drawing on real data from 101 private equity firms and leadership work across 65 portfolio companies, this episode provides a grounded look at what actually moved the market and why time is no longer a neutral factor in leadership decisions.

Learn more about Bespoke Partners and leadership strategy for private equity backed software companies: https://www.bespokepartners.com

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

The CFO market in private equity software is entering one of its tightest phases in years. Deal flow is rising, exits are coming back into view, and demand for proven financial operators is outpacing supply.

Join Eric Walczykowski, CEO of Bespoke Partners, for a timely discussion with our newest Partner, Marie Deller, who recently joined our Finance Executive Recruiting Practice. Together they explore the forces defining CFO hiring in 2026, including reduced candidate mobility, sharper value creation expectations, and shifting location requirements that are reshaping competitiveness across the market.

They also share why culture has become a strategic advantage in professional services and how Bespoke continues to support high performing leaders while solving the most complex financial officer searches in private equity backed software.

Hear what lies ahead for CFO recruiting in 2026.

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

In this new Tailored Talent episode, Eric Walczykowski talks with Katelyn Quaresma, Head of our Finance Practice, about the forces driving one of the tightest CFO and VP Finance markets in recent years. They examine why proven CFO supply has constricted, why number two roles are up more than fifty percent year over year, and how step up candidates and CFOO or CFO+ profiles are becoming critical to filling essential leadership gaps. Katelyn also covers shifting geo requirements, equity realism in compensation discussions, and what it takes to secure top financial talent as new platforms accelerate and exits approach.

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

Bespoke Partners CEO Eric Walczykowski joins Partner and Go-To-Market Practice Lead Tess Fischer for a deep dive into the shifting dynamics of go-to-market leadership across private equity-backed software companies. They discuss why turnover remains high, how compensation continues to climb, and what it takes to secure top talent as firms level up ahead of exits in an increasingly competitive market.

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

In this episode of Tailored Talent, CEO Eric Walczykowski sits down with Matt Sommi, Head of Private Equity Partnerships at Bespoke Partners, to discuss how his team creates alignment and continuity across multiple funds.

Eric and Matt explore how Bespoke’s partnership model and proprietary tools like the Executive Index and Calibrator deliver transparency, speed, and precision—transforming how private equity firms engage with search partners.

Join for insights about consultative pre-deal engagement, how Calibrator and the Executive Index provide real-time market insight, and why blending data with human expertise drives stronger leadership outcomes.

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

In this episode of Tailored Talent, Bespoke Partners CEO Eric Walczykowski sits down with Ryan Bonner, Partner and Head of our Product & Tech Leadership Practice, to discuss the surge in executive searches across technology and product leadership.

They explore how AI is transforming both roles, why offshoring strategies now require more nuanced leadership, and how customer-centric, P&L-driven product leaders are shaping value creation in PE-backed software and SaaS businesses.

Watch to learn more about how Bespoke Partners builds transformative leadership teams. 

Watch the video here 

Learn more about Bespoke Partners Product & Tech Leadership Practice

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/