Before you raise, see how your business runs

Deepdive equips founders with an inside look at the financial metrics VCs use to evaluate their business.

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How it Works

How it Works

Prepare for the most rigorous
diligence questions

Prepare for the most rigorous diligence questions

Deepdive helps founders handle questions that are typical during a fundraise.

  • How does your retention compare between new customers, and older ones?
  • How have your customer payback dynamics changed as you scaled?
  • What is the average revenue from your high-value vs low-value customers?
  • How capital efficient is your business?
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1-click effortless data ingestion
Stripe Chargebee



Discover what drives
your business

Deep Cohort Analysis

  • Build your cohorts accurately, regardless of your volume
  • Powerfully segment by any attribute like tier or geography
  • Automatically forecast newer cohorts using historical data
  • Export to Excel for more custom analysis

Insights into Your Business

  • Know the levers of your capital efficiency - your engine for growth
  • Leverage ML to create personas out of your customer data
  • Troubleshoot underlying business challenges
  • Analyze your churn and burn

Unique Venture Capital Lens

  • Get access to 20-years of VC experience baked into key metrics
  • Review the preflight check before your next financing round
  • Export financial summaries that any finance team will love
  • Embed ready-to-use charts that capture your progress directly into your board deck



Benchmark Your Startup

With over 20-years of investing, Headline has built the tools to discern both signals of success and potential warning signs. We are opening up our formulas — because we believe founders deserve the first look inside their businesses.

Payback Ratio Benchmark

Track your startup's return on growth spend with our Cumulative Gross Profit over CAC metric. Discover the rate that top tier startups recover their acquisition costs and benchmark your business against successful precedents to optimize growth and profitability.

Revenue Retention Benchmark

Discover where your startup stands among industry leaders with our comprehensive Revenue Retention metric. We tailor the analysis to your unique business model and age, providing invaluable insights and personalized feedback to help you stay ahead in the competitive landscape.

Lifetime Value Benchmark

Unlock the power of the Cumulative Revenue per Customer, also referred to as Gross Lifetime Value, to gain critical insights into your customer's lifetime spending. Our analysis not only computes this key metric but also reveals the factors influencing each customer's spending as they mature, empowering you with actionable data.

About Us

About Us

A free and private
tool, by Headline

Over the course of two decades, we've developed our own technology to help our investing team detect success signals and warning signs. We’re opening our formulas and processes — because we believe founders deserve the first look inside their businesses.


Get access to an investment professional for feedback

Follow Deepdive Guides to help simplify complex concepts

Keep your data completely private, unless you choose to share it

Brandon Brown


"Deepdive's 'Cumulative CAC Over S&M Spent' payback metric has become a critical KPI we use to monitor the efficiency of ramping up our customer acquisition efforts. We now use it in all our funding and board decks to properly visualize the return we get from investing in customer acquisition."

Peter Stacho


"At Polygon we're using Deepdive for accurate insights into our true customer LTV and how this is evolving over time, which is well beyond what Stripe reports could ever tell us. Simply dividing one with our annual churn rate and multiplying that with our average contract value is just a fictitious estimate."

Jett Fein

/Partner, Headline

"Headline led one of Gopuff's earliest rounds when many other investors struggled to understand the dynamics of a vertically integrated on-demand company. Deepdive gave us the x-ray vision we needed to partner with Gopuff early!"
Brandon Brown

Brandon Brown

\ COO,
Peter Satcho

Peter Satcho

\ Partner, Headline
Jett Fein

Jett Fein

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A Venture Capital Firm for
Technology Founders.

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