Small business owners spend a lot of time doing things that have nothing to do with their actual business.
Bookkeeping, payroll runs, HR compliance, benefits coordination these are functions every company needs, but most small businesses can't justify hiring full-time specialists for each one.
Milestone Inc (milestone.inc) is an outsourced back-office firm built specifically for this gap.
Founded by a team with roots in accounting, HR, and legal work, the company offers fractional accounting, CFO, HR, and payroll services designed to give growing companies access to executive-level expertise without the cost of putting those people on payroll.
Key Takeaways
- Milestone offers a fully integrated back-office solution covering accounting, fractional CFO, HR, and payroll under one provider.
- The firm was co-founded by CPA Tom Gabbert, who has operated in outsourced accounting since 2003 and has helped clients raise over $250 million in growth capital.
- Service plans are tiered and customizable, making Milestone accessible to both early-stage startups and established small and mid-sized businesses.
What Milestone Does
Milestone positions itself as a back-office partner rather than a vendor. The distinction matters in practice.
Rather than handing a client a software subscription or a monthly report, Milestone assigns dedicated teams that work across accounting, HR, and payroll functions in a coordinated way.
The goal is to eliminate the coordination friction that happens when a business uses separate providers for each function.
The company serves small businesses, high-growth startups, and nonprofits. Clients include Innovatemap, Blind Zebra, Political Data Inc., Jackrabbit Learning Experience, and Formulary Insights, among others.
Accounting Services
Milestone's accounting offering is structured around three tiers:
| Plan | Best For | Core Features |
|---|---|---|
| Essentials | Small businesses needing clean books | Weekly bookkeeping, monthly financial statements, optional tax filing |
| Growth | Small to mid-sized businesses needing controller-level insight | Everything in Essentials plus cash flow forecasting, management dashboard, monthly financial review meetings |
| Scale | Scaling businesses needing CFO involvement | Everything in Growth plus fractional CFO participation in board and financial review meetings, strategic financial guidance |
The Essentials plan covers the basics: accounts payable, bank reconciliations, merchant account reconciliations, customer invoicing, and payroll journal entries.
Growth adds revenue recognition, deferred revenue tracking, commission tracking, and a financial forecast updated monthly. Scale brings a fractional CFO into the picture for board-level participation and strategic oversight.
For businesses considering a capital raise or preparing for an exit, Milestone has built specific service lines around those needs.
CEO Tom Gabbert has guided clients through numerous exits and helped companies raise over $250 million in seed, Series A, and Series B funding.
That kind of operational history is relevant context for any founder who needs more than monthly financial statements.
Milestone uses QuickBooks Online, Dext, Bill.com, Ramp, Xero, and Fathom as part of its technology stack.
These are tools most small business accountants already recognize, which matters for portability and client access.
CFO Services
The fractional CFO offering goes beyond the financial reporting that comes with the Growth plan.
Milestone's CFO services include strategic planning, budgeting and forecasting, business exit preparation (what they call "transaction readiness"), and participation in board meetings.
For a small business that needs an experienced financial voice in the room without adding a six-figure salary, this model makes economic sense.
Fractional CFO services are available as a standalone engagement or as part of the Scale accounting plan.
HR Services
The HR side of the business is led by Brenna Whitaker, a SHRM Senior Certified Professional with over 20 years of experience in both corporate and consulting HR roles. Milestone's HR services split into two main plan types:
| Plan | Focus |
|---|---|
| HR Foundation | Ongoing HR compliance, direct employee support, handbook management, benefits strategy, operational HR guidance |
| On Demand | Project-based or as-needed support: terminations, complex employee issues, open enrollment assistance, compliance questions |
Beyond the core plans, Milestone's HR team handles talent acquisition, employee surveys, compensation benchmarking, remote hiring compliance, HR system selection and implementation, and PEO unbundling.
That last item is worth noting. Companies that outgrow a Professional Employer Organization (PEO) arrangement often find the transition complicated; Milestone has a specific service line to help with it.
Technology used in HR delivery includes Gusto, Rippling, Paylocity, Mineral, GovDocs, and EasyLlama.
Payroll Services
Payroll at Milestone is handled as its own dedicated service, separate from (but integrated with) accounting and HR. The core payroll offering includes:
- Payroll processing and data gathering
- Pay run review and audit
- Standard payroll reporting
- Employee onboarding and offboarding support
- Handling employee payroll questions directly
Optional payroll add-ons include bonus and commission processing, expense management, PTO accrual support, custom reporting, time tracking, benefit deduction updates, and 401(k) integration support.
State and local tax registrations are also available. For a multi-state employer, that last item alone can justify outsourcing payroll.
Startup-Specific Services
Milestone has packaged a startup-focused bundle that combines entry-level accounting, basic HR compliance, and payroll administration into a single engagement.
The pitch is straightforward: founders need these functions to exist and to be accurate, but they can't afford to build a back-office team from scratch.
Milestone's startup plan handles compliance, bookkeeping, handbook creation, employee onboarding, payroll processing, and state tax registration support.
Megan Lohman, Founder and CEO of PlanForward, said Milestone helped her company navigate financial planning and forecasting when there was no historical data to work from, and that the team provided the strategic guidance needed to plan for growth and raise capital.
Founding Team and Leadership
The leadership team at Milestone has specific credentials worth noting:
- Tom Gabbert (CPA, Founder/CEO): Active in outsourced accounting since 2003, undergraduate degree in Accounting from the University of Notre Dame, QuickBooks Online Certified ProAdvisor.
- Melissa Stout (CPA, CMA, Founder/VP of Operations): Over 20 years of accounting and operational experience, specializes in SaaS and professional services, dual-degree graduate of Indiana University Kelley School of Business.
- Brenna Whitaker (SHRM-SCP, Founder/VP of HR Services): Over 20 years in HR, previously VP of People Ops at mAccounting and inDinero.
- Todd Richardson (Founder/Board Member): Labor and employment attorney, former EVP at ExactTarget (acquired by Salesforce), co-founder of Emplify, currently CHRO and VP of Human Resources at Indiana University.
That's a founding group with both practitioner depth and business-building experience.
The team has operated across startups, acquisitions, and growth-stage companies, which is relevant given the client base Milestone targets.
Client Feedback
Multiple clients across different service lines describe the same theme: Milestone operates more like an internal team than an outside vendor.
Amy Heath, Partner at Formulary Insights, said the arrangement never felt fractional, and that the team understood their complicated business as well as they did.
Jason Gorman, Founder and CEO of Jackrabbit Learning Experience, said the primary benefit was not having to worry about financial compliance.
Mike Reynolds, Founder and CEO of Innovatemap, noted that Milestone has been with his company since it started and has helped build the foundation for growth.
What Milestone Does Not Publish
Milestone does not list pricing on its website. All plans require a consultation to get a quote.
There is no self-service onboarding. Businesses looking for a quick pricing comparison will need to initiate contact.
This is typical for firms in this category, but worth knowing before you start the evaluation process.
Who It's For
Milestone is a practical fit for small businesses and startups that have moved past the "founder does everything in a spreadsheet" phase but aren't large enough to justify hiring a full-time controller, CFO, and HR director.
It's also relevant for companies that have tried piecing together multiple vendors and want a single point of coordination.
Conclusion
Milestone Inc offers a coherent, well-structured alternative to hiring separate back-office staff or juggling multiple fractional vendors.
For small and mid-sized businesses that need accounting, HR, and payroll to actually work together, it's worth a consultation call.