About Us

Milestone is not your typical professional services firm

We are making a difference for all those entrepreneurs who are out there making a difference every day.

At Milestone, we do what we do because we enjoy working with small business owners and being a part of their success.

Milestone is not your typical professional services firm. We believe in true business partnerships and approach every client interaction with this goal in mind: to make your life easier, provide you access to information to make smarter decisions, and to help you build a more successful company.


Our team is your team, and our model is simple: You get experienced C-Level leadership at a fraction of the cost of a full-time resource. We promise no long term contracts, no hassles, and the flexibility to scale up or down as your business needs change.  Because every business deserves access to strategy and expertise, no matter their size.

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At Milestone our core values are more than just words, it's who we are.  They form the foundation of our firm and serve to guide us in building relationships with clients, team members, and partners.  We call them our Core4.


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We are committed to do our best - for our clients, for each other, for our business, and for our community. With each client and project, we demonstrate this commitment by going the extra mile in everything we do, providing value that exceeds expectation, and helping one another realize our goals and potential. We also understand the importance of serving our community and strive to leave the world a little better than we found it. 


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We have a deep respect and admiration for entrepreneurs. After all, we're entrepreneurs ourselves. So, like the business leaders we work with, we are innovative, forward-thinking, and dedicated to creative problem-solving. We are leading the way in vetting new technology and providing expert guidance to our clients, all while creating a framework that allows us to grow and develop new leaders from within.


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Who we are is just as important as what we achieve. We approach each client and every situation with honesty, integrity, and a firm code of ethics. We "practice what we preach” and apply this same code of ethics to our interactions with each other.   


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We are passionate about our clients and the value we create for them, but that's not the whole story. We also value and respect our own personal goals for growth and development. We believe the more well-rounded, engaged and, well, “balanced" we are, the better we're able to help our clients and each other. 



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Tom Gabbert  CPA

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.  


He enjoys traveling and spending time with his family.  He is also an avid history buff and die-hard Cubs fan.  

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Melissa Stout  CPA, CMA

Founder / VP - Accounting Services

Melissa is a seasoned CFO with over 20 years of accounting and finance experience.  Her knowledge of accounting systems and integrated workflow platforms helps her utilize the latest, cutting edge tools to streamline financial operations and maximize efficiency.  She is passionate about helping entrepreneurs succeed by combining technology and process with financial insights. Melissa has worked with a wide variety of clients, specializing in accounting and business issues unique to the software-as-a-service (SaaS) and professional services industries.  

In addition to her CPA certification, Melissa is a Certified Management Accountant (CMA) who holds an undergraduate degree from the Indiana University Kelley School of Business, with dual majors in accounting and marketing.

She enjoys spending time with her husband and two children and is an avid sports fan, following the NFL and college basketball in her spare time.

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Brenna Whitaker  SHRM-SCP

Founder / VP - HR Services

Brenna leads our HR Services practice and oversees everything HR at Milestone.  She has over 15 years of Human Resources experience, both in consulting and working in corporate HR Roles.  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.  

Company culture, employee engagement, development, and designing foundational processes are particular passions, but she is an avid learner and enjoys continuously adding new tools to her skillset. 

Brenna is a graduate of Indiana State University and a SHRM Senior Certified Professional.


Brenna lives in Noblesville with her husband and two young children. Current hobbies include falling asleep watching Netflix and folding laundry. She hopes to develop additional hobbies when her children are older. 

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Todd Richardson  

Founder / Advisor

Todd is passionate about employee engagement and supporting businesses through all of their people-related needs. A labor/employment and business attorney by trade, Todd began his career in private practice before becoming General Counsel and head of HR for the (then) fifth largest private residential real estate company in the U.S. Following his time in real estate, he served as EVP, Administration at ExactTarget, which was acquired by Salesforce.

After ExactTarget, Todd went on to found, run, and consult with multiple companies, including Emplify (co-founder), Ntracts (CEO), and Cheetah Digital (Chief Administrative Officer). Todd currently serves as the CEO of EDGE Mentoring.