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>Justworks made $982.7M in FY2021, an increase of 33% over FY2020.</li><li>Justworks has raised $143M from investors such as FirstMark Capital, Union Square Ventures, and Bain Capital.</li><li>Justworks has two levers to increase its SaaS revenue: subscription price and the number of employees it covers.</li></ul>

Justworks made $982.7M in FY2021, an increase of 33% over FY2020.Justworks has raised $143M from investors such as FirstMark Capital, Union Square Ventures, and Bain Capital.Justworks has two levers to increase its SaaS revenue: subscription price and the number of employees it covers.

<ul><li>Sacra estimates that Gusto generated $975M of revenue in 2025, up 30% year-over-year from $750M in 2024.</li><li>The customer base increased from 300,000 direct SMB customers and 700,000 via partners in August 2024 to over 400,000 direct customers by March 2025.</li><li>Gusto was valued at $9.3B during a $200M employee tender offer in June 2025.</li></ul>

Sacra estimates that Gusto generated $975M of revenue in 2025, up 30% year-over-year from $750M in 2024.The customer base increased from 300,000 direct SMB customers and 700,000 via partners in August 2024 to over 400,000 direct customers by March 2025.Gusto was valued at $9.3B during a $200M employee tender offer in June 2025.

<ul><li>Sacra estimates that Rippling hit $1B in annualized revenue in March 2026, up from $850M at the end of 2025 and growing 78% year-over-year.</li><li>Rippling is valued at $16.8 billion following its May 2025 Series G round, in which the company raised $450 million in new financing and announced a tender offer to repurchase up to $200 million of equity from current and former employees.</li><li>Rippling operates a B2B SaaS model with subscription pricing determined by employee count and the modules utilized.</li></ul>

Sacra estimates that Rippling hit $1B in annualized revenue in March 2026, up from $850M at the end of 2025 and growing 78% year-over-year.Rippling is valued at $16.8 billion following its May 2025 Series G round, in which the company raised $450 million in new financing and announced a tender offer to repurchase up to $200 million of equity from current and former employees.Rippling operates a B2B SaaS model with subscription pricing determined by employee count and the modules utilized.

<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>It&#39;s supposed to be north of 50% of the population in the next five to 10 years, and there are more freelancers today than there were yesterday.</li><li>We&#39;re saving significant time and money for companies, and we provide a much better experience for the end contractors.</li><li>We just have more conviction than ever.</li></ul>

It&#39;s supposed to be north of 50% of the population in the next five to 10 years, and there are more freelancers today than there were yesterday.We&#39;re saving significant time and money for companies, and we provide a much better experience for the end contractors.We just have more conviction than ever.

Anthony Mironov, CEO Of Wingspan, On The Convergence In back-office SaaS

United States

Justworks Inc operates as a human resource technology company. The Company offers human resource and payments paltform for automated payments, payroll, HR admin, benefits enrollment, and government paperwork. Justworks serves customers in the United States.

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Justworks (JW US)

Primer: Justworks - 10 Mar 2026

Payroll and benefits software for SMBs to manage HR, compliance, and payments

Sacra

Primer: Gusto - 16 Jul 2026

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

Sacra

Primer: Rippling - 10 May 2026

Workforce management software unifying HR, IT, and contractor payroll for global teams

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

Anthony Mironov, CEO Of Wingspan, On The Convergence In back-office SaaS

Sacra interview with Anthony Mironov, CEO of Wingspan.

Sacra

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