Milestone

Tom Gabbert

Founder / CEO

Tom Gabbert has been a pioneer and thought leader in the outsourced accounting industry since 2003. He is a successful entrepreneur who loves helping fellow entrepreneurs realize their dreams. Tom understands the unique challenges of starting, growing, and exiting a business. Not only has he done it twice himself, but he has guided numerous clients over the years through successful exits. Along the way, Tom has also helped his clients raise over $250M in growth capital (seed, Series A, Series B). He has a unique background that combines extensive financial and operational experience with a proven track record of client success.

Tom is a Certified Public Accountant and holds an undergraduate degree in Accounting from the University of Notre Dame.

tbgabbert

Trusted by Entrepreneurs Who’ve Made It to the Other Side

20+

Years Experience

400+

Clients Served

SHRM-SCP

Certified

3

HR Leadership Roles

About Brenna

people ops

talent acquisition

company culture

strategic hr

hr compliance

outsourced hr

employee relations

With over 20 years of Human Resources experience, including both corporate and consulting roles, Brenna is a seasoned People Ops leader. She excels in her ability to keep the needs and objectives of the organization top of mind while still remaining a strong advocate for the team, company culture, and strategic HR initiatives.

Prior to Milestone, Brenna served as VP of People Ops at both mAccounting and inDinero — two rapidly-scaling, tech-enabled professional services firms. In those roles, she built HR infrastructure from scratch, navigated complex employment challenges, and shaped cultures that supported significant growth.

As a co-founder of Milestone, Brenna’s philosophy is simple: every business deserves access to executive-level HR expertise, regardless of size.

She brings the same strategic rigor to a 10-person startup as she would to a 500-person enterprise.

Brenna lives in Westfield, Indiana with her husband and two young children. Her current hobbies include falling asleep watching Netflix and folding laundry — though she plans to develop additional hobbies when her kids are older.

Education & Credentials

Bachelor of Business Administration (B.B.A.), Accounting

University of Notre Dame

Notre Dame, IN

Certified Public Accountant

State of Indiana

as seen in

  • “Indianapolis HR leaders on building culture-first teams”

    Indianapolis Business Journal

  • “The hidden HR risks that could sink your startup”

    Entrepreneur

  • “Why fractional HR is the future of people operations”

    Forbes

  • “Building compliant onboarding programs at scale”

    HR Dive

  • “5 signs your small business has outgrown informal HR”

    SHRM.org

Recent Posts by Tom

How Do I Categorize Income and Expenses Correctly To Avoid Tax and Reporting Issues?

If your financial reports never quite add up or your CPA keeps flagging the same issues every tax season, the culprit is likely one of these common categorization mistakes hiding in your QuickBooks.

How Do I Prepare My Books So They’re “Tax Ready” For My CPA Or Accountant?

If handing your books to your CPA feels more stressful than it should, this guide walks you through exactly what tax-ready books look like and the simple steps to get there before the scramble starts.

When Should I Consider Professional Help Instead Of DIY QuickBooks Setup?

A DIY QuickBooks setup can work in the early stages, but as your business grows, the cracks start to show. Miscategorized transactions, unreliable financial reports, and tax season scrambles are all signs your setup may be working against you. Here is how to know when it is time to bring in a pro.

View Our Blog

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Get executive-level HR guidance without the full-time cost. Let Brenna and the Milestone team become your people operations partner.

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