Transaction type experience
Equity fundraising, debt raising, majority sale, minority sale, management buyout and merger are distinct disciplines. The counterparties differ, the documentation differs and the negotiation dynamics differ.
An advisor with fifteen venture rounds behind them may have limited exposure to a private equity buyout process, and the reverse is equally true. Establish which category your transaction falls into and check experience against that category rather than against corporate finance in general.
Stage experience
Seed, Series A, growth equity and mature company transactions are different environments. Seed rounds turn on team and narrative, Series A on early evidence of a repeatable model, growth rounds on unit economics and efficiency, mature deals on cash generation and durability.
An advisor who works mainly with profitable mid-market companies will apply the wrong valuation logic to a loss-making growth business, and one who works mainly with venture-stage companies may under-prepare for the depth of financial diligence a private equity buyer runs.
Sector experience
Sector knowledge shows up in three places: which metrics buyers and investors care about, which counterparties are active, and how the business is framed.
For software, that means net revenue retention, gross margin structure, contract length and expansion patterns. For services, utilisation, project mix and client concentration. For hardware, unit economics, supply chain and inventory. For regulated businesses, licences, approvals and compliance history.
You can test this quickly. Ask which three metrics buyers in your sector will focus on and why. A specialist gives a specific answer immediately.
Counterparty coverage
Experience with the specific counterparty type matters. Selling to a strategic acquirer, to a private equity platform and to a portfolio company as a bolt-on are three different negotiations with different price logic and diligence intensity.
The same applies to fundraising. Venture funds, growth funds, family offices, corporate venture arms and debt providers each evaluate differently. Ask which of these the advisor has closed with in the past two years.
Functional depth
Beyond process, look for the specific skills your situation demands: financial modelling, valuation, negotiation, diligence management, cross-border structuring or investor relations.
If your model is weak, an advisor with genuine modelling depth is worth more than one who outsources it. If the likely sticking point is an earn-out structure, prioritise someone who has negotiated several.
Role and recency
Two filters remove most of the noise. First, what was the person's role: lead, supporting team member, specialist or reviewer. Second, when: work from the past two to three years reflects current market conditions, and older work reflects a market that no longer exists.
An advisor with four relevant, recent, lead-role transactions is usually a stronger choice than one with twenty older transactions in supporting roles.
Experience that transfers and experience that does not
Process discipline, negotiation instinct and the ability to keep several parties moving transfer across sectors and deal types. Buyer and investor relationships, sector-specific valuation judgement and knowledge of a particular diligence standard do not.
That distinction tells you how to fill gaps. A strong generalist plus a sector-experienced non-executive or a specialist diligence provider can cover what a single hire does not.