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.

<ul><li>Now at a Sacra-estimated $1.15B in annualized revenue, up 70% YoY, Deel is colliding with Rippling & Gusto as global payroll goes domestic & vice versa as all three fight to own the full stack of payroll & HR.</li><li>Expanding from contractor payments, Deel launched EOR services (late 2020) to help companies hire full-time employees abroad, and then into global payroll (mid 2022) to unify compliance, tax & payments across their entire team, scaling from $4M annualized revenue in early 2020 to $295M by end of 2022, reaching an estimated $1.15B by August 2025 (up 70% YoY) at a $12.6B valuation for a 11x multiple.</li><li>After burning sub-$10M in 2021 and turning profitable in 2022, Deel has continued expanding its margins, hitting 16% EBITDA margin in 2025 with ~85% gross margins (vs. ADP at 46%), positioning the company for its stated goal of going public as early as 2026-2027.</li></ul>

Now at a Sacra-estimated $1.15B in annualized revenue, up 70% YoY, Deel is colliding with Rippling & Gusto as global payroll goes domestic & vice versa as all three fight to own the full stack of payroll & HR.Expanding from contractor payments, Deel launched EOR services (late 2020) to help companies hire full-time employees abroad, and then into global payroll (mid 2022) to unify compliance, tax & payments across their entire team, scaling from $4M annualized revenue in early 2020 to $295M by end of 2022, reaching an estimated $1.15B by August 2025 (up 70% YoY) at a $12.6B valuation for a 11x multiple.After burning sub-$10M in 2021 and turning profitable in 2022, Deel has continued expanding its margins, hitting 16% EBITDA margin in 2025 with ~85% gross margins (vs. ADP at 46%), positioning the company for its stated goal of going public as early as 2026-2027.

Employment Hero / Private Capital Markets

<ul><li>Employment Hero is defending its core market for HR & payroll while opening a North American beachhead via its acquisition of Humi in Canada.</li><li>Sacra estimates Employment Hero reached $163M in annual recurring revenue (ARR) in January 2025, up from $155M in December 2024 and $110M in December 2023.</li><li>Now geographic expansion has brought its competitors to Australia’s shores, with Deel and Rippling both invading Australia in 2024 going after Employment Hero's core geography where it serves 20% of all private companies.</li></ul>

Employment Hero is defending its core market for HR & payroll while opening a North American beachhead via its acquisition of Humi in Canada.Sacra estimates Employment Hero reached $163M in annual recurring revenue (ARR) in January 2025, up from $155M in December 2024 and $110M in December 2023.Now geographic expansion has brought its competitors to Australia’s shores, with Deel and Rippling both invading Australia in 2024 going after Employment Hero's core geography where it serves 20% of all private companies.

<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

United States

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

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Wingspan (WINGSPAN US)

Primer: Wingspan - 24 Aug 2026

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

Sacra

Deel At $1.15B/year Growing 70%+ YoY

TL;DR: Rising domestic labor costs and COVID catalyzed Deel’s explosive growth as a service that let startups hire globally from day one. Now at a...

Sacra

$163M/year Gusto Of Australia

TL;DR: With Deel and Rippling invading Australia, Employment Hero is defending its core market for HR & payroll while opening a North American...

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

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