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>Guideline hit $120M in annual recurring revenue (ARR) in June 2024, up 35% year-over-year, after crossing $100M ARR at the end of 2023.</li><li>On August 27, 2025, Gusto announced its agreement to acquire Guideline, further consolidating its position in the small business retirement plan market.</li><li>Guideline has achieved a 10% market share among new 401(k) plans, indicating strong traction in the small business segment.</li></ul>

Guideline hit $120M in annual recurring revenue (ARR) in June 2024, up 35% year-over-year, after crossing $100M ARR at the end of 2023.On August 27, 2025, Gusto announced its agreement to acquire Guideline, further consolidating its position in the small business retirement plan market.Guideline has achieved a 10% market share among new 401(k) plans, indicating strong traction in the small business segment.

<ul><li>One out of three US workers now does some form of contract or freelance work on a 1099—up from 10% in 2005—a trend that has accelerated & gone “upmarket” as the rise of frontier model AI labs has created huge demand to hire physics PhDs, software engineers, lawyers & others on short-term data labeling contracts.</li><li>Standard back-office SaaS & payments tools (Chase Bill Pay, QuickBooks, Gusto) can handle 5-10 contractors fine, but at 50+ the operational burden explodes—insurance certificates need verification across dozens of formats, state-by-state compliance multiplies, and payment reconciliation becomes full-time work.</li><li>Payroll platforms, professional employer organizations (PEOs), and vertical SaaS platforms alike are all going after the opportunity to handle mixed W-2/1099 workforces to prevent churn & prevent payments leaking outside their platforms to Bill.com & Quickbooks, with the divergent approaches of building their own contractor rails (Rippling) vs. partnering with contractor payroll platforms like Wingspan (Insperity).</li></ul>

One out of three US workers now does some form of contract or freelance work on a 1099—up from 10% in 2005—a trend that has accelerated & gone “upmarket” as the rise of frontier model AI labs has created huge demand to hire physics PhDs, software engineers, lawyers & others on short-term data labeling contracts.Standard back-office SaaS & payments tools (Chase Bill Pay, QuickBooks, Gusto) can handle 5-10 contractors fine, but at 50+ the operational burden explodes—insurance certificates need verification across dozens of formats, state-by-state compliance multiplies, and payment reconciliation becomes full-time work.Payroll platforms, professional employer organizations (PEOs), and vertical SaaS platforms alike are all going after the opportunity to handle mixed W-2/1099 workforces to prevent churn & prevent payments leaking outside their platforms to Bill.com & Quickbooks, with the divergent approaches of building their own contractor rails (Rippling) vs. partnering with contractor payroll platforms like Wingspan (Insperity).

Anthony Mironov, CEO Of Wingspan, On Why 1099s Are Eating Payroll

<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>Finch was founded in 2020 by Jeremy Zhang and Ansel Parikh in San Francisco to address the fragmentation problem in employment systems.</li><li>Finch&#39;s rapid growth is evident in its metrics: over 10,000 employers and 1 million employees connected, processing 5 million daily API calls.</li><li>Finch&#39;s competitive advantage lies in its extensive integration network and its ability to provide a single, standardized interface for a highly fragmented market.</li></ul>

Finch was founded in 2020 by Jeremy Zhang and Ansel Parikh in San Francisco to address the fragmentation problem in employment systems.Finch&#39;s rapid growth is evident in its metrics: over 10,000 employers and 1 million employees connected, processing 5 million daily API calls.Finch&#39;s competitive advantage lies in its extensive integration network and its ability to provide a single, standardized interface for a highly fragmented market.

<ul><li>We last spoke last April, when our company was doing over $80 million ARR.</li><li>Guideline announced hitting $100M ARR in January of this year.</li><li>We&#39;re now over $120M, growing 35%+ year-over-year.</li></ul>

We last spoke last April, when our company was doing over $80 million ARR.Guideline announced hitting $100M ARR in January of this year.We&#39;re now over $120M, growing 35%+ year-over-year.

Kevin Busque And Steven Wu, CEO And CFO Of Guideline, On Hitting $120M ARR

United States

Payroll software for SMBs to manage employee and contractor payments, taxes, and benefits

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Gusto (GUSTO US)

Primer: Guideline - 30 Aug 2025

Software for small businesses to offer affordable, employer-sponsored 401(k) retirement plans

Sacra

Anthony Mironov, CEO Of Wingspan, On Why 1099s Are Eating Payroll

Let's start with Wingspan and its evolution. You've definitely taken more on over time, going from a contractor-first platform, to helping...

Sacra

Primer: Pilot - 07 Dec 2024

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

Sacra

Primer: Finch - 02 Sep 2024

API for accessing and writing data across fragmented HR and payroll systems

Sacra

Kevin Busque And Steven Wu, CEO And CFO Of Guideline, On Hitting $120M ARR

Sacra interview with Kevin Busque and Steven Wu, CEO and CFO of Guideline.

Sacra

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