An operator for your portfolio. Due diligence is one of the jobs.
For VC firms, venture debt funds, lenders, angels and family offices. Before you wire, the job is usually operational due diligence: how the company runs, and where the plan is likely to break. Written at deal pace.
Not investment advice.
An execution-readiness read on whether the team can deliver the plan. The investment decision stays with you.
of what investors made on 2024 exits came from the company growing.
Bain & Companyof failed startups failed because of the team.
CB Insightsfeatures out of 100 are the ones people actually use.
Pendo 2024One assessment. Six things I look at.
Processes, systems and culture, read for what they say about productivity, quality and continuity. A surface read on how the company runs, not a code audit. Where a deal needs a specialist, I say so.
How the work moves
Who decides, where work queues, where handoffs drop things, and how long it takes from a decision to something delivered.
Whether the systems help or get worked around
The tools people use every day, judged by whether the work goes through them or around them.
What quality costs to hold
What gets redone, what reaches the customer and comes back, and how much of the week goes on that.
What depends on named people
Where knowledge sits in one person's head, and what stalls while they are away.
Founders, team and how decisions get made
Decision patterns under pressure, and the distance between the stated culture and the observed one.
The first 90 days
If you invest, what the first 90 days should cover, in priority order.
Before and after you invest.
Before the money moves
Operational diligence on the target. Can the processes, the systems and the team carry the plan being pitched?
At deal paceInside the company after
Interim cover when a lead leaves, or an owner for a launch or migration.
Per job, as it comes upBefore the next round
A readiness check ahead of a follow-on or a refinancing.
Ahead of each raiseInside your own process
An operational section added to your own underwriting checklist.
OnceOur internal knowledge is an asset. Why hand it to an outsider?
Every engagement starts with a signed mutual NDA and a signed scope. Access is limited to what the job requires.
How long does it take?
It is timed to your deal. The scope and timeline are agreed in writing before I start.
Questions people ask.
Our internal knowledge is a competitive asset. Why would we hand it to an outsider?
Every engagement starts with a signed mutual NDA and a written scope before any work begins, and the confidentiality obligations continue after the engagement ends. Access is limited to the systems and documents the specific job requires. Nothing from one client is carried into another, and no client work becomes a case study, named or unnamed, without written permission.
What is operational due diligence?
Operational due diligence (Operational DD) is a pre-investment assessment of how a target company actually operates - processes, team structure, decision-making, organizational maturity, and execution capability. Unlike financial DD (which examines numbers) or legal DD (which examines contracts), operational DD examines whether the company can execute on its plan. It's typically done by VCs before Series A and beyond.
Is this technical due diligence?
No. Technical due diligence opens the codebase and reviews architecture, code quality and security posture, and it is a specialist job. May's assessment is a surface read on how the company runs: whether the systems people use every day carry the work or get worked around, what that costs in productivity and rework, and what depends on named individuals. Where a deal needs a code-level or security review, she says so and it is scoped separately.
Do you assess AI claims as part of operational DD?
Only at the level of the process behind it. The question asked is whether the AI in the deck maps onto work the company actually does today and whether anyone in the team operates it. It is not a model evaluation and not a review of the data architecture. Companies frequently pitch AI on top of a process nobody has fixed, and that gap shows up in an operational read. A deeper technical review is a separate, specialist engagement.
Do you support portfolio companies post-investment?
Yes. After an investment, a portfolio company can bring May in as an interim or fractional product and program manager: cover when a lead leaves, or an owner for a launch or migration. She already knows the company from the diligence.
How long does a DD engagement take?
It is timed to your deal: one assessment, scoped to what the deal needs, with the scope and timeline agreed in writing before the work starts. The final report is a confidential PDF with a clear execution-readiness verdict.
What's included in the DD report?
Confidential 15-25 page report covering: executive summary with an execution-readiness verdict, how the work moves and where it queues, whether the systems carry the work or get worked around, what quality costs in rework, key-person and continuity risk, red flags requiring deal terms or post-close action, and prioritized recommendations for the first 90 days after investment.
What does operational due diligence cost?
It is one assessment, scoped and priced to the deal, with the scope written down before the work starts. One operator carries the engagement end to end: M.Sc in AI, a product and program management background, and 10+ years in fintech, digital banking and adtech.