Milestone

Tom Gabbert

Founder / CEO

CPA and entrepreneur with 20+ years in outsourced accounting, Tom has helped clients raise over $250M in growth capital and guided numerous businesses through successful exits.
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 Tom

people ops

talent acquisition

company culture

strategic hr

hr compliance

outsourced hr

employee relations

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.

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

A Guide To Outsourced Accounting Costs in 2026

Getting three quotes for outsourced accounting often produces three wildly different numbers for what sounds like the same work, and the difference usually comes down to scope no one spelled out. This guide covers 2026 pricing ranges by service tier and business size, and the variables that move a quote before you ever sign anything.

7 differences between book keeping and accounting

7 Differences Between Bookkeeping And Accounting

Most small business owners use “bookkeeper” and “accountant” interchangeably, but hiring the wrong one or missing the other entirely could leave your finances exposed at exactly the wrong moment.

How much should I pay someone to do my QuickBooks

How Much Should I Pay Someone To Do My Quickbooks?

A bookkeeper is a financial professional who is responsible for recording and maintaining the day-to-day financial transactions of a business.

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