Equity Research interview preparation
Sell side and buy side. Every question is either traced to a named firm from a public candidate report, or tagged at desk level when we could not trace it. Answers lead with the point, then the mechanism, then the limitation.
100 questions, mapped to the firms that asked them
- Questions
- 100
- Traced to a firm
- 72
- Firms
- 45
- Updated
- September 2026
037How would you model a subscription software business, and what metrics matter?Insight PartnersSoftware · New York · 2022Piper SandlerInvestment Banking · Burlingame · 2026
Say this
Model the recurring revenue base by cohort rather than the income statement. Opening ARR, plus new, plus expansion, less churn and downgrades, gives closing ARR. Everything else follows from that roll-forward.
Then walk it
- The ARR bridge is the model. Once you have opening ARR, new bookings, expansion and churn, revenue is largely determined, because recognised revenue is a lagging function of the contracted base.
- Key metrics: net revenue retention, gross retention, gross margin, customer acquisition cost payback, and the rule of forty which is growth plus free cash flow margin.
- Net retention above 110 percent is the single most important number, because it means the installed base grows without selling anything new. That is what justifies a high revenue multiple.
- Watch the gap between billings, revenue and deferred revenue. Billings lead revenue, so a slowdown shows up in billings a quarter or two before it hits the reported line. That is often where the variant view lives.
- Cost side: gross margin tells you how much real compute or support sits in cost of revenue, sales and marketing efficiency tells you whether growth is bought or earned, and R&D as a share of revenue tells you about future product.
- And take stock-based compensation seriously, because in software it is large enough to determine whether the company is profitable at all.
Where candidates lose it
Modelling revenue directly and ignoring the ARR bridge and deferred revenue. Also quoting the rule of forty without knowing whether it uses free cash flow margin or operating margin, since the two give very different answers.
Expect next
- What is the rule of forty?
- Why do billings lead revenue?
- What net retention would justify a 10 times revenue multiple?
Reported by candidates at Insight Partners (Software, New York, 2022); Piper Sandler (Investment Banking, Burlingame, 2026). Source: Wall Street Oasis.
045How would you value a company with no earnings?Piper SandlerInvestment Banking · New York · 2026Sequoia CapitalVenture Capital · San Francisco · 2021
Say this
Move up the income statement until you reach a line that is meaningful, then value that. Revenue multiples, gross profit multiples, or a forward-year earnings estimate discounted back to today.
Then walk it
- First ask why there are no earnings. A company spending heavily on growth is completely different from one with a broken cost structure, and only the first deserves a growth valuation.
- For growth-stage losses: EV to revenue, or better, EV to gross profit, since gross profit strips out the differences in cost of revenue between a software company and a delivery company.
- Then normalise: model forward to the year the business reaches a steady-state margin, apply a mature multiple to that year's earnings, and discount back. This forces you to state when profitability arrives and what it looks like.
- For asset-heavy or distressed cases, value the assets instead: net asset value, replacement cost, or liquidation value.
- For very early stage, the market approach dominates: what did comparable companies raise at, and what did similar businesses exit for.
- The discipline that matters: any revenue multiple is an implicit bet on a future margin. Saying 'six times revenue' without saying what terminal margin justifies it is not a valuation.
Where candidates lose it
Reaching for a revenue multiple with no view on terminal margin. Also failing to distinguish a company choosing to lose money from one unable to make money. That distinction determines whether the question is valuation or restructuring.
Expect next
- What terminal margin justifies that multiple?
- When do they reach profitability?
- Why is it difficult to value a first-year firm?
Reported by candidates at Piper Sandler (Investment Banking, New York, 2026); Sequoia Capital (Venture Capital, San Francisco, 2021). Source: Wall Street Oasis.
Firm tags come from public, anonymous candidate reports on Wall Street Oasis: strong signal, not sworn testimony. Firms are named as the places a question was reported, not as partners of Fin Maverick. Answers are written for this page to show how to think out loud; they are not scripts to recite.

