Private Markets, Angel and Secondary Investing, Sacra

Sacra

Private Markets, Angel and Secondary Investing

Bringing transparency to private markets so investors, founders, and employees can build on conviction. Sacra delivers deeply researched insights on the private companies shaping tomorrow's markets. By surfacing the data, context, and operator perspective that are missing from private markets today, we help secondary buyers and sellers price equity accurately and unlock liquidity for the people building these businesses.

Private Capital Markets

<ul><li>Light raised a $30 million Series A in September 2025 led by Balderton Capital.</li><li>Light rebuilds the entire back office of scaling companies around an AI-native general ledger.</li><li>Oracle NetSuite dominates the mid-market ERP space and is adding AI capabilities to defend against AI-native challengers.</li></ul>

Light raised a $30 million Series A in September 2025 led by Balderton Capital.Light rebuilds the entire back office of scaling companies around an AI-native general ledger.Oracle NetSuite dominates the mid-market ERP space and is adding AI capabilities to defend against AI-native challengers.

<ul><li>Pilot hit about $43M ARR in 2022, up 30% from the year before.</li><li>Pilot announced crossing 1,000 customers in 2020, and was at roughly 1,700 at the end of 2022, with an average revenue per customer of around $25,000.</li><li>SMBs today spend about $60B per year on bookkeeping and accounting, meaning Pilot today has only 0.4% penetration into the market.</li></ul>

Pilot hit about $43M ARR in 2022, up 30% from the year before.Pilot announced crossing 1,000 customers in 2020, and was at roughly 1,700 at the end of 2022, with an average revenue per customer of around $25,000.SMBs today spend about $60B per year on bookkeeping and accounting, meaning Pilot today has only 0.4% penetration into the market.

<ul><li>The dawn of JavaScript and automating repetitive tasks came first, and there were many things that it couldn&#39;t handle.</li><li>Now, the exciting thing is we&#39;re at a new inflection point with AI and the technologies that GPT-3 brings to us.</li><li>Now, we can read those invoices and contracts with AI and make a recommendation for what it is.</li></ul>

The dawn of JavaScript and automating repetitive tasks came first, and there were many things that it couldn&#39;t handle.Now, the exciting thing is we&#39;re at a new inflection point with AI and the technologies that GPT-3 brings to us.Now, we can read those invoices and contracts with AI and make a recommendation for what it is.

Alex Lee, CEO Of Truewind, On The Potential Of GPT-powered Bookkeeping

<ul><li>Pilot (dataset) has hit 60% gross margins acting as human-in-the-loop middleware between the SMB finance stack and the bookkeeping system of record in QuickBooks.</li><li>Sacra estimates that Pilot has $43M in annual recurring revenue (ARR) growing 30% year-over-year with industry leading gross margins at 60%.</li><li>Every SMB needs bookkeeping and accounting and today they spend some $60B/yr on it, meaning Pilot today is a leader with only 0.4% penetration into a massive opportunity.</li></ul>

Pilot (dataset) has hit 60% gross margins acting as human-in-the-loop middleware between the SMB finance stack and the bookkeeping system of record in QuickBooks.Sacra estimates that Pilot has $43M in annual recurring revenue (ARR) growing 30% year-over-year with industry leading gross margins at 60%.Every SMB needs bookkeeping and accounting and today they spend some $60B/yr on it, meaning Pilot today is a leader with only 0.4% penetration into a massive opportunity.

Pilot: The $43M Per Year Mechanical Bookkeeper

<ul><li>We talked to Andy to get his perspective on the last 8 years of evolution in the tech-enabled bookkeeping space, the geographical labor arbitrage behind the business models of InDinero and Pilot, and the steelman case for the upside of companies like Pilot.</li><li>We opened the office in The Philippines and we did that labor arbitrage.</li><li>Another platform that does really well is Xero.</li></ul>

We talked to Andy to get his perspective on the last 8 years of evolution in the tech-enabled bookkeeping space, the geographical labor arbitrage behind the business models of InDinero and Pilot, and the steelman case for the upside of companies like Pilot.We opened the office in The Philippines and we did that labor arbitrage.Another platform that does really well is Xero.

Andy Su, co-founder Of InDinero, On tech-enabled Bookkeeping's 14-year Evolution

United States

Software for AI-assisted bookkeeping and financial workflows for venture-backed startups

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Truewind (TRUEWIND US)

Primer: Light - 25 Sep 2025

AI-powered finance platform for automating accounting, bookkeeping, and financial reporting

Sacra

Primer: Pilot - 07 Dec 2024

Tech-enabled bookkeeping service with human-in-the-loop built on top of QuickBooks

Sacra

Alex Lee, CEO Of Truewind, On The Potential Of GPT-powered Bookkeeping

Sacra interview with Alex Lee, co-founder and CEO of Truewind.

Sacra

Pilot: The $43M Per Year Mechanical Bookkeeper

TL;DR: Pilot ($43M ARR) has hit 60% gross margins acting as human-in-the-loop middleware between the SMB finance stack and the bookkeeping system...

Sacra

Andy Su, co-founder Of InDinero, On tech-enabled Bookkeeping's 14-year Evolution

Sacra interview with Andy Su, co-founder of InDinero.

Sacra

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