About Self Bill Pro
Self Bill Pro is a Technology company based in Clermont (United States) founded in 2023 by Josh Winigrad. Self-billing platform for insurance and employee benefits is provided. It operates in the Technology and Financial Services sectors. Self Bill Pro has raised $3.65 million across 2 funding rounds. Self Bill Pro offers products and services including Self-Bill Summaries and Self-Bill Detail Files. Its focus areas include FinTech, Alternative Lending, Online Lenders and Consumer Loans. Its competitors include DailyPay, Earnin and Optum; 3 of its 3 listed competitors have raised funding.
Company details
Self Bill Pro was founded in 2023 in Clermont, United States, within the HR technology sector. A platform is operated to facilitate self-billing for insurance and employee benefit funds. Accurate self bills are generated for HR departments using real-time enrollment data. Employers are supported in calculating and paying premiums for their employee benefits through this streamlined process.
- Headquarters Clermont, United States
- Founders Josh Winigrad
- SectorsTechnologyFinancial Services
- Email••••••••
- Phone•••• ••••
- Website selfbillpro.com
- Social LinkedIn
- Total Equity Funding$3.65M (USD)
in 2 rounds
- Latest Funding Round$2.6M (USD), Seed
Sep 2025
Products & Services of Self Bill Pro
Self Bill Pro offers a comprehensive portfolio of products and services, including Self-Bill Summaries and Self-Bill Detail Files.
Generates PDF summaries of self-bill charges for carriers.
Provides spreadsheets with employee-level charges for HR.
Funding Insights of Self Bill Pro
Self Bill Pro has successfully raised a total of $3.65M across 2 strategic funding rounds. The most recent funding activity was a Seed round of $2.6 million completed in September 2025. This substantial capital infusion reflects strong investor confidence in the company's business model, growth potential, and market opportunities. The funding enables strategic expansion, product development, market penetration, and operational scaling to drive long-term value creation and competitive advantage.
- Total Funding $3.65M
- Total Rounds 2
- Last Round Seed — $2.6M
- First Round $1.05M
(Apr 2024)
All 2 funding rounds of Self Bill Pro with amounts and investors; the two latest post-money valuations are shown, the rest are part of the premium plan.
| Date | Amount | Transaction Name | Valuation | Lead Investors | Investors |
|---|---|---|---|---|---|
| Sep 2025 | $2.6M | Seed | – | – | – |
| Apr 2024 | $1.05M | Seed | – | – | – |
People of Self Bill Pro
1 people are tracked at Self Bill Pro (1 in leadership).
| Name | Role | Group |
|---|---|---|
Josh Winigrad | Founder | Leadership |
Complete people profiles for Self Bill Pro
Full employee and board profiles, team structure, tenure and professional contact details require an active premium plan.
- Full employee list
- Team structure
- Board tenure
- Professional contacts
Verified entity values are shown only after access is granted.
Timeline of Self Bill Pro
3 dated milestones of Self Bill Pro across 2 years, from founding to its latest funding, stage changes and deals.
- Founded Self Bill Pro is founded.
- Funding First funding round of $1.0M.
- Funding Latest funding round, Seed, of $2.6M.
Competitors of Self Bill Pro
Self Bill Pro has 3 listed competitors in our database, 3 of them funded. They include DailyPay, Earnin and Optum.
| Company Name | Domain | Founded | HQ Location | Total funding | Employees | Description |
|---|---|---|---|---|---|---|
| dailypay.com | 2015 | New York, United States | $264M | 845 | Developer of an online platform for employee financial benefits | |
| earnin.com | 2012 | Palo Alto, United States | $190.1M | 242 | Real-time access to earned wages is provided fee-free. | |
| optum.com | 2011 | Eden Prairie, United States | $250,000 | 140 | Optum is recognized as a leading health solution and care delivery organization. |
Detailed competitors of Self Bill Pro
The full competitor set, operating metrics and side-by-side benchmarks require an active premium plan.
- Full competitor set
- Operating metrics
- Benchmarks
- Competitive positioning
Verified entity values are shown only after access is granted.
Web traffic of Self Bill Pro
The website of Self Bill Pro (selfbillpro.com) receives about 1.2K visits a month.
- Monthly visits1.2K
▲ 83.6% vs previous month
Top companies in HR & Workforce Technology
3 companies that operate in the same segment as Self Bill Pro (HR & Workforce Technology) in United States, ranked by their profile score on The Company Check.
| Company | Description | Founded | Location | Total funding | Revenue | Employees |
|---|---|---|---|---|---|---|
Anonymous employee reviews and job search platform are operated. | 2007 | San Francisco, California, United States | USD 201.5 M | 1,695 | ||
Cloud-based LMS platform for IT industry | 2004 | Farmington, Utah, United States | USD 235.41 M | USD 4.95 M | 1,774 | |
Employee health benefits are facilitated via a cloud-based platform. | 2007 | Plymouth Meeting, Pennsylvania, United States | USD 228.3 M |
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Frequently Asked Questions about Self Bill Pro
Self Bill Pro was founded in 2023 and raised its 1st funding round 1 year after it was founded.
Self Bill Pro is headquartered in Clermont, United States. It is registered at Clermont, Florida, United States.
Self Bill Pro is a funded company, having raised a total of $3.65M across 2 funding rounds to date. The company's 1st funding round was a Seed of $1.05M, raised on Apr 2024.
Self Bill Pro was founded in 2023 in Clermont, United States, within the HR technology sector. A platform is operated to facilitate self-billing for insurance and employee benefit funds. Accurate self bills are generated for HR departments using real-time enrollment data. Employers are supported in calculating and paying premiums for their employee benefits through this streamlined process.
Self Bill Pro offers Self-Bill Summaries and Self-Bill Detail Files.