Tailored Talent

Finding AI-Adept CEOs: What Sponsors Need to Know

“If you are thinking about changing your CEO, act on it sooner rather than later.” The SaaS landscape is shifting faster than most private equity -backed software companies can adapt. AI is reshaping every product roadmap, every go-to-market [https://www.bespokepartners.com/software-sales-marketing-customer-success-go-to-market-recruiting/] motion, and every leadership expectation. The CEO who worked five years ago may not be the CEO who creates value today. In this Tailored Talent panel discussion, Bespoke Partners CEO Eric Walczykowski brings together the firm's CEO, Board and P&L practice leaders for a candid conversation on what is changing in the executive market and how the best sponsors are responding. Katherine Baker, Partner and CEO Practice Lead, Jenny Gray, Partner and CEO Practice Expert, and Alex Bossetta, Partner and CEO Practice Expert, cover the full landscape: the rise of the product-leaning CEO, how AI fluency is being assessed when there are no 30-year resumes to lean on, why there are roughly 100 executives in the world who have run a software company above 500 million in revenue, and what sponsors need to do differently to land the right leader in a market where the best candidates are fielding 20 to 30 calls in the first two weeks after a deal is announced. This is the conversation happening inside the most active CEO search [https://www.bespokepartners.com/ceo-search-chief-executive-officer-recruiting/] practice in private equity-backed software. Bespoke Partners has placed more CEOs [https://www.bespokepartners.com/ceo-search-chief-executive-officer-recruiting/] in PE-backed software than any other firm in the world. What the team shares here reflects what they are seeing on the ground every day. 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/ [https://www.bespokepartners.com/private-equity-talent-report/?pod]

More Than a Closer: The GTM Standard Private Equity Boards Hold To in 2026 | Tailored Talent with Andrew Reynolds

The best salesperson at the helm is no longer enough. Private equity boards have raised the bar, shifted the metrics they scrutinize, and raised their expectations of what a go-to-market leader needs to deliver. The leaders who are winning in PE-backed software in 2026 look different from the ones who won five years ago.   In this episode of Tailored Talent, Bespoke Partners CEO Eric Walczykowski sits down with Andrew Reynolds, Partner in our Go-to-Market practice, to break down exactly what Private equity boards are demanding and what the winning go-to-market profile looks like.   Topics covered:  - How PE board scrutiny has shifted from ARR growth to profitability metrics: LTV to CAC, CAC payback, and sales efficiency ratios  - Why the go-to-market scorecard leads with metrics: what candidates inherited, what they moved it to, and how they did it  - How backchannel validation and AI tool usage reveal whether a candidate can deliver versus just talk about it - The multi-playbook athleticism PE-backed platforms are looking for and where that model breaks down at scale  - The $250M ARR inflection point where the go-to-market structure needs to consolidate under one leader  - Why end market experience is non-negotiable in complex verticals and what six months of ramp costs in a five-year hold  - How compensation structure is shifting: EBITDA-oriented bonuses replacing bookings targets, and deeper equity diligence from candidates  - The three go-to-market leader attributes that will define the difference-makers in 2026   -- Tailored Talent is the Bespoke Partners vodcast featuring candid conversations on the talent decisions shaping private equity-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/ [https://www.bespokepartners.com/private-equity-talent-report/?pod]

Talent and Value Creation: The CEO's Executive Team Decisions

The most consequential decisions in a PE hold are not the ones made in the boardroom. They are the ones made about people.  Which executives to bring in, when to make changes, how to build the right measurement infrastructure before you hire the revenue leader, and why the CFO search is structurally harder than most people will admit.   In Part 2 of this Tailored Talent conversation, Bespoke Partners CEO Eric Walczykowski continues his discussion with Patrick Dennis, CEO of Avaya, former CEO of Venafi, shifting to the executive team decisions that determine whether a value creation plan actually gets executed.   Topics include:  * Why Patrick hires to the season, not the destination, and what the special forces executive model looks like in practice  * The cascade effect of a CRO change and why a year of rebuild is 20 to 25 percent of a five-year hold  * Why revenue operations should be built before the CRO is placed  * What Patrick wants from a CRO: forecast accuracy, consistency, and transparency, not just growth  * The structural tension that makes the CFO search the hardest in PE-backed software   Watch Part 1 [https://youtu.be/chMG3Ocptrg] Watch Part 2 [https://youtu.be/1T07z3QiNN8] 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/ [https://www.bespokepartners.com/private-equity-talent-report/?pod]

The CEO's Private Equity Playbook: Leading a Sponsor-Backed Company

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/ [https://www.bespokepartners.com/private-equity-talent-report/?pod]

The CRO Who Wins Exits: What the Profile Looks Like Now

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/ [https://www.bespokepartners.com/private-equity-talent-report/?pod]