+127%

est. 2Y upside i

FinTechHR TechSeries B

Wingspan is the first payroll platform purpose-built for contractor management. Our unified platform helps companies save time, improve retention, and stay compliant by automating the contractor lifecycle. Built for contingent work, Wingspan streamlines onboarding, automates payments, handles 1099s, and offers benefits for contractors.

Rank

#215

Sector

Fintech, Payroll Software

Est. Liquidity

~3Y

Data Quality

Data: Low

Wingspan offers meaningful upside if it hits public-comparable multiples: from $46M ARR to ~$73M in 2 years, a 5x exit gives ~145% net return.

Last updated: August 3, 2026

Bull (20%)+252%

Revenue reaches ~$73M by 2027 and exit multiple expands to 7x on IPO hopes or category leadership, yielding ~$513M exit; after 20% dilution upside is ~252%.

Base (55%)+146%

Revenue grows to ~$73M and multiple converges to ~5x, in line with public comps, producing ~$366M exit; after 20% dilution upside is ~145%.

Bear (25%)-14%

Multiple compresses to 2x on competitive pressure or delayed exit, exit ~$147M barely above $54M preference; after dilution return is ~-14%.

Est. time to liquidity~3.0 years

Preference Stack Risk

severe

Funding Intensity

39%

Total preferred liquidation preference is $54M, representing 39% of the $138M valuation, so common equity is only ~$84M at current mark.

Dilution Risk

high

With $24M raised in July 2025 and revenue at $46M, a follow-on round is likely within 2 years; assumed 20% dilution.

Secondary Liquidity

limited

Secondary market mark exists but employee liquidity is likely limited; M&A offer signals possible exit.

View all 10 open roles at Wingspan →

Last updated: March 10, 2026

Questions to Ask at the Interview

Strategic questions based on Wingspan's data — designed to show you've done your homework.

  • 1

    “How does Wingspan defend against Intuit/Gusto adding contractor-only payroll features?”

  • 2

    “What are net revenue retention and gross margin trends by customer segment?”

  • 3

    “How is the option strike priced relative to the $138M secondary mark, and are there employee repurchase rights?”

Community

Valuation Sentiment

Our model estimates +127% upside. What do you think?

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Disclaimer: This analysis is AI-generated and does not constitute financial or career advice. Always conduct your own due diligence.