Promising technology gets sidelined in diligence rooms. Not because the product does not work, but because organisational structure is unclear, hiring plans are reactive, or leadership gaps are left unaddressed. Alex Randall Kittredge, a fractional executive and advisor to high-growth start-ups, has spent nine years leading transformation efforts across Fortune 100 companies, Series A to E start-ups, and $14 billion in M&A deals under boardroom scrutiny. His view is that many founders pitch product-market fit, while sophisticated VCs evaluate team-market fit. They are asking whether the current team can scale from five to 50 or 500. “Investors don’t just bet on tech. They bet on teams,” says Kittredge. “Sophisticated VCs are evaluating team-market fit.” Building investor confidence requires embedding strong talent signals early through succession planning and role clarity, and codifying how you scale, not just who you hire.
Embedding Strong Talent Signals Early
Most founders focus pitch energy on product-market fit, revenue traction, customer validation, and technical milestones. Sophisticated VCs also evaluate whether the current team can scale. “I’ve sat in diligence rooms where even promising tech gets sidelined because the org structure is unclear, hiring plans are reactive, or leadership gaps aren’t addressed,” Kittredge explains. VCs assess not just current capability, but scalability.
Can the founding team that validated product-market fit from zero to one also scale operations from one to ten? Can early hires who thrived in chaotic start-up environments adapt to more structured, growth-stage operations? Companies without clear answers raise execution-risk concerns that either kill deals or reduce valuations. “Embedding strong talent signals early, like succession planning, role clarity, or even a lightweight org roadmap, sends a message. We’re not just building product, we’re building capability,” Kittredge notes.
Succession planning means identifying critical roles, clarifying what happens if key people leave, and demonstrating a realistic understanding of the capability gaps that will emerge at scale. Role clarity means defining responsibilities and decision rights clearly enough that teams do not duplicate effort or leave critical work unowned. Lightweight org roadmaps show how structure evolves as headcount grows. Together, these artifacts demonstrate intentionality and reduce perceived execution risk.
Codifying How You Scale, Not Just Who You Hire
Many start-ups focus on headline hires, a VP of Sales or Head of Product, without articulating the operating model and integration plan beneath those appointments. “Smart investors ask, what’s your plan for integrating these leaders? What’s the operating model beneath them?” Kittredge explains. Headline hires create value when they integrate successfully. They create problems when role expectations are unclear, decision rights conflict with existing leadership, or operating models do not support the functions they are hired to build. “In one Series A deal, I helped a founder reduce churn risk by outlining a three-phase talent integration plan and a board-ready succession chart,” Kittredge notes. “This wasn’t just nice to have. It accelerated the term sheet by two months. Why? Because it reduced perceived execution risk.”
The three-phase integration plan clarified how new functional leaders would onboard, which decisions they would own immediately versus over time, and how their functions would scale over 18 months. The board-ready succession chart identified backup leadership for critical roles. Deals move faster when investors can see that growth will not depend on improvised management, unclear handovers, or fragile single points of failure. Without integration plans, VCs model a higher probability of leadership churn, slower ramp times, and organizational dysfunction.
“You don’t need a full HR function, but you do need talent ops that reflect intentionality,” Kittredge emphasizes. That means documenting how hiring decisions are made, how new leaders integrate, how performance is measured, and how succession planning is handled. It does not require dedicated HR headcount. It requires a systematic approach to how talent decisions support the business strategy.
Signaling Coachability Through Leadership Development
VCs watch leadership maturity closely, including willingness to bring in coaches, openness to 360 feedback, and how culture is discussed under pressure. “When founders proactively invest in leadership development, even through peer coaching, advisory boards, or fractional executive leadership, it signals a growth mindset,” Kittredge explains. “And in VC terms, that’s pure gold.”
VCs assess not only the team’s current capability, but also its capacity to grow into the roles the company will require at scale. First-time founders who can build products do not automatically have the skills to lead 100-person organizations. The question becomes whether they can develop those skills, and whether they know when to bring in experienced operators. Founders who engage executive coaches, seek 360-degree feedback, join peer-CEO groups, or work with fractional executives demonstrate awareness of gaps and commitment to closing them. Even tools like a quick eNPS survey can matter, because they signal a willingness to gather feedback and act on organizational health indicators before they become an issue.
Building Investor Confidence Through Talent Signals
“Embedding talent signals early isn’t just a nice-to-have. It’s a competitive differentiator,” Kittredge concludes. “It builds investor confidence, shortens deal timelines, and sets the foundation for scale.” Companies that pitch product-market fit without addressing team-market fit face higher execution-risk assessments that either kill deals or reduce valuations. Companies that embed strong talent signals reduce perceived risk and accelerate fundraising timelines.
The Series A example is a reminder of what is at stake. Two months of runway saved can be the difference between raising on favorable terms and accepting dilutive financing.
Embed strong talent signals through succession planning and role clarity. Codify how you scale through integration plans and operating models. Signal coachability through leadership development investments. When these elements align, talent strategy stops being an afterthought and becomes a differentiator that builds investor confidence and shortens deal timelines.
Connect with Alex Randall Kittredge on LinkedIn for insights on building investor trust through early talent strategy.
Alex Randall Kittredge is an American entrepreneur, author, and strategic advisor based in New York who specializes in business transformation, M&A integrations, and the concept of “portfolio careers”. He is the founder of APR Strategic Consulting and publishes the ARK Strategy newsletter on Substack, where he discusses the evolution of work in the post-AI economy. He is the author of the forthcoming book, “How Your Side Hustles Will Save You: Creating a Durable Career that Transcends the Corporate Ladder”
