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>Wingspan raised $24M in Series B funding in July 2025, led by Touring Capital, bringing total capital raised to $54M.</li><li>Wingspan provides an all-in-one platform designed specifically for onboarding, paying, and supporting independent contractors, freelancers, and gig workers.</li><li>The big opportunity for Wingspan is to build a closed loop payments network for the $1.4T and growing of freelancer payments made every year.</li></ul>

Wingspan raised $24M in Series B funding in July 2025, led by Touring Capital, bringing total capital raised to $54M.Wingspan provides an all-in-one platform designed specifically for onboarding, paying, and supporting independent contractors, freelancers, and gig workers.The big opportunity for Wingspan is to build a closed loop payments network for the $1.4T and growing of freelancer payments made every year.

Employment Hero / Private Capital Markets

<ul><li>Sacra estimates that Employment Hero hit $163M ARR in January 2025.</li><li>Employment Hero raised A$263 million in a Series F round led by TCV in October 2023, bringing total funding to A$650 million.</li><li>Employment Hero&#39;s recent revenue growth corresponds to its geographic expansion from Australia into the UK, Southeast Asia, and Canada, facilitated by its acquisition of Toronto-based Humi.</li></ul>

Sacra estimates that Employment Hero hit $163M ARR in January 2025.Employment Hero raised A$263 million in a Series F round led by TCV in October 2023, bringing total funding to A$650 million.Employment Hero&#39;s recent revenue growth corresponds to its geographic expansion from Australia into the UK, Southeast Asia, and Canada, facilitated by its acquisition of Toronto-based Humi.

<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>Rain raised $75 million in a Series B round led by Prosus in April 2025, bringing total funding to $191 million.</li><li>Rain plans to launch an EWA-secured credit card in late 2025 that automatically adjusts credit limits based on employees' real-time accrued wages.</li><li>Rain's embedded integration within Workday positions the company to access Workday's 65 million employee footprint, with native placement potentially driving 2-3x higher employee penetration rates compared to standalone apps.</li></ul>

Rain raised $75 million in a Series B round led by Prosus in April 2025, bringing total funding to $191 million.Rain plans to launch an EWA-secured credit card in late 2025 that automatically adjusts credit limits based on employees' real-time accrued wages.Rain's embedded integration within Workday positions the company to access Workday's 65 million employee footprint, with native placement potentially driving 2-3x higher employee penetration rates compared to standalone apps.

<ul><li>In the last year, I wouldn’t say the strategy has changed dramatically.</li><li>Cards are only getting more important.</li><li>The benefit with vertical SaaS companies is, because they&#39;re vertical, they can know an incredible amount about this very specific kind of business.</li></ul>

In the last year, I wouldn’t say the strategy has changed dramatically.Cards are only getting more important.The benefit with vertical SaaS companies is, because they&#39;re vertical, they can know an incredible amount about this very specific kind of business.

Matt Brown, Partner At Matrix Partners, On Emerging Trends In Fintech And AI

United States

Financial wellness platform offering earned wage access and financial tools for employees

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Rain App (APP US)

Primer: Wingspan - 24 Aug 2026

Payroll and compliance software for companies managing large networks of independent contractors

Sacra

Primer: Employment Hero - 27 Aug 2025

Cloud-based platform for businesses to manage HR, payroll, and employee benefits

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: Rain App - 24 Jul 2025

Financial wellness platform offering earned wage access and financial tools for employees

Sacra

Matt Brown, Partner At Matrix Partners, On Emerging Trends In Fintech And AI

Sacra interview with Matt Brown, partner at Matrix Partners and co-founder of Bonsai.

Sacra

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