Prepalyst has 22 portfolio & diligence interview questions with model answers, covering reference calls, technical diligence, term sheets and preference stacks. Every question is graded on technical accuracy, completeness and interview communication. Practice is free.
22
Questions
7
Easy
7
Medium
8
Hard
1.Calculate the Dilution from an Option Refresh
Easy
Portfolio associates are expected to explain simple cap-table changes clearly to founders and investment partners.
A portfolio company has 8.0m fully diluted shares before a financing and needs to create a 400,000-share option refresh immediately before the round. Calculate the dilution to existing holders from the refresh alone. Why…
Financial AnalysisCommonly asked at Sequoia, Benchmark, Greylock~8 min
A basic portfolio-support question used to test financial discipline.
A portfolio company has $18m of cash, burns $1.2m per month today, and expects burn to rise by $0.1m per month for the next six months. How do you assess runway and when should it start fundraising?
Financial AnalysisCommonly asked at First Round Capital, Founders Fund, General Catalyst~7 min
Portfolio reviews reveal whether candidates can recognise when a clean-looking metric is misleading.
A founder reports net revenue retention of 118%, but finance calculates 104%. How do you resolve the difference before using the metric in a board meeting?
Financial AnalysisCommonly asked at Bessemer Venture Partners, Battery Ventures, Sapphire Ventures~7 min
6.Set Useful Quarterly Objectives for a Portfolio Company
Easy
A portfolio-support interview tests whether you can turn a broad company ambition into a small set of accountable operating objectives.
A seed-stage B2B software company says its quarterly goal is to "grow faster." How would you help the CEO turn that into useful objectives and key results without creating a reporting exercise?
Venture InvestingCommonly asked at First Round Capital, Initialized Capital, Founders Fund~7 min
A board-level portfolio case tests whether you can separate a capability gap from a difficult quarter before recommending a leadership change.
A Series B company's VP Sales has missed plan for two quarters. The CEO asks whether the board should push for a replacement before the next fundraise. How do you make the recommendation?
Venture InvestingCommonly asked at Accel, Kleiner Perkins, NEA~11 min
A common partner-meeting exercise for a fund deciding whether to defend ownership.
Your fund owns 12% of a company. A new investor is leading a round at twice the prior valuation. What work do you do before deciding whether to take your pro rata?
Investment ThesisCommonly asked at General Atlantic, Coatue, Thrive Capital~10 min
14.Use an Investor Introduction to Test Enterprise Demand
Medium
A portfolio-platform case asks you to create value through a customer introduction without substituting a warm email for real go-to-market work.
A Series A security startup asks its VC for introductions to enterprise customers. Build the workflow for deciding whom to introduce and how you would measure whether the support was useful.
Due DiligenceCommonly asked at Andreessen Horowitz, Bessemer Venture Partners, Battery Ventures~10 min
A senior portfolio judgement question about price, structure and fiduciary discipline.
A portfolio company cannot raise at its last valuation. The founder asks existing investors to lead a flat round with aggressive preferences. What do you recommend?
Deal AnalysisCommonly asked at Sequoia, SoftBank, Tiger Global~13 min
A board-level portfolio case involving founder incentives, governance and an unusually large secondary request.
A Series C company is raising $60m primary capital at a $500m pre-money valuation. The founder asks to sell $15m of personal shares in the same round. Growth is strong, but the company has missed two product deadlines.…
Venture InvestingCommonly asked at Index Ventures, Benchmark, Accel~14 min
17.Intervene When AI Revenue Growth Masks Margin Risk
Hard
A portfolio-support case for an AI application company scaling revenue faster than its infrastructure economics.
A portfolio company has doubled ARR to $20m, but gross margin fell from 72% to 48% as enterprise customers use more inference-heavy features. Management wants to accelerate sales hiring before the next raise. What would…
Financial AnalysisCommonly asked at Andreessen Horowitz, Bessemer Venture Partners, General Catalyst~14 min
Tests whether you understand that headline valuation and actual economics diverge.
A company raises $100m at a $1bn post-money with a 1x non-participating preference. It later sells for $400m. What do the investors and common holders receive? Then explain how the answer changes with a 2x participating…
Venture InvestingCommonly asked at Insight Partners, Sequoia, Andreessen Horowitz~12 min
A VC portfolio-diligence case where an associate must use scarce founder and finance-team access to decide whether a bridge round funds a financeable business.
You are diligencing a proposed $12m Series A bridge for RelayOps, a workflow-software portfolio company. The investment committee meets tomorrow, management can answer only a limited number of questions, and the company…
Due DiligenceCommonly asked at Bessemer Venture Partners, Battery Ventures, Accel~18 min
Tests whether you can make portfolio-level decisions when financing conditions deteriorate rapidly.
Public multiples have fallen sharply and your fund's portfolio companies will struggle to raise. How do you triage the portfolio over the next 30 days?
Portfolio ConstructionCommonly asked at Initialized Capital, NEA, Craft Ventures~13 min
Firm names indicate where a question type is commonly reported in interviews. They are not sourced from, endorsed by, or affiliated with the firms named.
Portfolio & Diligence Interview Questions (22 with Model Answers) · Prepalyst