The Leadership Risk Most Investors Miss
- Nadine Blackie
- Apr 23
- 3 min read
In every deal, investors evaluate product strength, market traction, runway, and financial performance. But what about the people leading the business?
Leadership is one of the riskiest assets in a startup and also the least interrogated.
Titles and past companies don’t show you how the leadership team is currently operating, how decisions are made under pressure, or whether the team is actually built for what’s next.
After years inside high growth startups and participating in due diligence processes ourselves, we saw a recurring blind spot:
A high-level summary of the leadership team’s LinkedIn profiles — and little else.
No insight into leadership team cohesion.
No real understanding of founder dynamics and impact.
No way to assess how the leadership team would operate under the weight of post-raise scale.
Why Vesta DD Exists
Vesta DD is The Vesta Club’s leadership due diligence offering, designed for venture capital and private equity firms who want a deeper, sharper view of the team they’re backing.
Our work begins during deep due diligence, after the term sheet is signed, but before the subscription agreement is executed, and well before the cheque clears.
This is when assumptions are being tested, warranties are being drafted, and risk is being actively mitigated.
Most diligence focuses on the commercial engine. Which is critical, but without the right people stoking the fire behind the business, returns rarely meet expectations.
We help you assess the leadership engine and whether it’s equipped to support the next phase of growth.
What We Deliver
We offer two engagement paths, both tailored to fit the stage and complexity of your deal. Each includes a variation of:
1:1 structured interviews with the leadership team
Team health and alignment insights covering trust, ownership, communication, and clarity
An assessment of leadership strengths, risks, and scale readiness
Our Firepower Insight path includes a comprehensive report with actionable recommendations that set the team up for success, commercially and culturally.
We apply high-trust frameworks like The Five Dysfunctions of a Team and Radical Candor, adapted for high-growth environments and investor relevance.
This is not a culture audit or tick the box HR check. It’s a deep dive into leadership dynamics and their direct impact on post-deal execution.
Why It Matters Post-Term Sheet
The leadership team shapes both execution and employee experience. When cohesion is low or clarity is missing, symptoms show up fast:
Founder dependency
Bottlenecked and slow moving decisions
Poor functional alignment and inefficient cross-team ways of working
Talent churn and communication breakdowns
Execution drag (just when the business needs to move faster)
Vesta DD helps you spot these risks early and build the right support plan before they impact performance.
What Traditional Diligence Misses — and Why It Matters
Most investment firms run robust diligence across commercial, legal, and technical aspects of a deal. But the leadership layer? It’s often summarised in a slide deck or skimmed over in a founder interview.
Here’s where traditional diligence typically falls short:
As AI reshapes how companies operate, leadership teams need more than good titles and instincts. They need to be protecting space to be asking:
Are we staffed correctly to leverage AI for speed, efficiency, and sustainability?
Can our wider leadership team implement AI responsibly, without introducing unnecessary business or data risk?
Are we evolving role scopes and team structures fast enough to match the opportunities AI unlocks?
Vesta DD isn’t about throwing up red flags. It’s about bringing clarity, so investments are backed with conviction and know how to support with precision.
Built for Investors Who Know the Team Is the Real Bet
We work with VC and PE firms across Australia, APAC, Canada, and the US — regions where we’ve built the deepest experience and know the leadership landscape best. Whether you’re leading a Seed or Series A round, or acquiring a growth-stage business, Vesta DD adds insight where there’s typically only instinct.
This isn’t about de-risking a deal entirely. It’s about bringing laser focus and deeper clarity to the structure, support, and scale required post-investment.
Want to Know Who and What You’re Really Backing?
Let’s talk about how Vesta DD can strengthen your diligence process.
Book a confidential call or call us at +61 466 583 325
