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

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.

Payback Ratio Benchmark

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.

Payback Ratio Benchmark

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

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Nicole Clark

Nicole Clark

/CEO, Trellis Law

"Utilizing Deepdive's segmentation analysis, we were able to obtain a granular insight into the distinct retention patterns of our enterprise versus non-enterprise customers. We could break up our overall retention into unique segments to provide context on what is truly driving the topline numbers. Deepdive made what was once a complex task into a simple and actionable UI."
Bianca Padilla

Bianca Padilla

/CEO, CareWell

"Deepdive's segmentation analysis transformed the way we look at our customer base. By offering granular insights into the various retention patterns of our customer types, it unlocked a precise understanding of customer lifetime value across different segments. This insight allowed us to allocate our customer acquisition budget more strategically and efficiently. What was once a complex task has been made simple and actionable through Deepdive's user-friendly interface."
Brandon Brown

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 Satcho

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."
Oz Uzuner

Oz Uzuner

/VP of Product & Growth, Poplin

"As a data driven organization, we are getting tremendous value from Deepdive, and it complements our internal BI perfectly. And being able to share, analyze, and review our data with Headline only makes the process and relationship better and bigger for us. This level of support is hard to come by from investors, it's a really refreshing approach and a value add provided by Headline!"

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