The Milestone Approach

We are making a difference for the entrepreneurs out there making a difference every day.

Milestone is not your typical professional services firm. We believe in true business partnerships that make life easier, provide the best information to make smarter decisions, and help clients build successful companies.

Our team is your team, and our model is simple: You get decades of executive-level leadership at a fraction of the cost of a full-time resource. Because every business deserves access to strategy and expertise, no matter their size.

We partner with your business to provide the best possible answers facing your business today, tomorrow, and down the line.

We are the trusted HR and Accounting partner for businesses of all sizes and specialties


“Milestone has been a great partner for our growing company. We initially engaged them to help us identify gaps in our HR infrastructure, but it quickly evolved into a recurring role for both Accounting and HR support. They help us think strategically about our back office functions and how to leverage them to help us achieve our goals as a company.”

Giselle Hale COO – Political Data, Inc.

“We use Milestone for both our HR and Accounting functions and they are incredible. They helped us build the infrastructure we were missing, but more importantly helped position us strategically to get to the next level. I would recommend Milestone to anyone looking to transform their back office functions into a competitive advantage.”

Chase Flashman Co-Founder & CEO – ShipSights

“When we launched our company, we turned to Milestone to cover our back office needs and they have been fantastic. They helped us get our HR and Accounting infrastructure in place so that we could focus on growing our business. Milestone is a great resource for start-up and scale-up companies.”

Jim Koepke Managing Director – Insider US

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.

Be Growth Minded

Every situation is a learning opportunity. We consistently strive to build our skillset, identify efficiencies, and discover ways the collective “we” can improve. The status quo simply isn’t enough. We encounter new challenges and situations on a daily basis and appreciate the opportunity that creates to expand our knowledge base. We collaborate and ask for feedback knowing that results are more important than ego, and that the combined experiences of our team outweigh our individual abilities.

Be Outcomes Focused

Every problem has a solution. We start with the end in mind – what is the outcome our internal and external customers are looking to achieve? We approach each situation with the intent to discover the problem to be solved – and then we solve it. Externally, we keep our clients’ short, mid, and long-term goals in mind to create reasonable, scalable solutions. We take a step back first and then we zoom in. Internally, we strive for connection between our individual contributions and company objectives, letting us better understand the role we have in moving our company forward.

Be Someone Others Want to Work With

Every team member has the ability to make those around them better. The work is hard and some days are certainly better than others, but ultimately, we choose to be here and to champion our mission because we believe in our ability to positively impact organizations. We respectfully challenge each other because that kind of challenge leads to growth and best-case outcomes for all involved. Being someone others want to work with also means we are balanced individuals. Although we are passionate about what we do, work isn’t our whole world and it doesn’t define us. Be Kind. Be Helpful. Genuinely Care. There is no place here for drama, but healthy debate is always welcome.

Be An Example of Accountability

Everyone owns something and every contribution is necessary. In a collaborative environment we can’t succeed unless we all hold up our end of the bargain. This starts with delivering, as promised, every time. We are accountable to our clients, to each other, and to ourselves. We are not perfect but we own our mistakes. We make the difficult decisions and hard calls – even when we don’t want to.


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.

Melissa Stout CPA, CMA

Founder / VP – Client Services

Melissa oversees client operations at Milestone. She is seasoned financial executive with over 20 years of accounting and operational 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 leveraging best-in-class technology platforms with proven strategies for process improvement. 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 two children and is an avid sports fan, following the NFL and college basketball in her spare time.

Brenna Whitaker SHRM-SCP

Founder / VP – HR Services

With over 15 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 the VP of People Ops at both mAccounting and inDinero.

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.

Todd Richardson

Founder / Board Member

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 CHRO and Vice President for Human Resources at Indiana University.

Leadership team

Pat McDonald

Managing Director / Client CFO





Pat brings a wealth of knowledge to his role as the Managing Director of the Market Readiness division, where he helps business owners prepare for an anticipated financial transaction, whether it’s a capital raise, a refinancing, or a sale of the company.   Pat came to Milestone with extensive experience as a Chief Financial Officer working in private equity across multiple industries, including healthcare technology, hospitality and leisure, manufacturing and consumer products. He is well versed in M&A transactions, forecasting, cash flow planning, corporate and private taxation, internal controls, compensation modeling, systems implementation, insurance exposure, and benefits administration. 

Ellen Elpers

Director – Technology Services




Ellen started her career in outsourced accounting as a staff accountant working closely with Melissa Stout, and quickly rose through ranks to emerge as the leader of the Technology Services group.  Ellen has the rare combination of strong technical accounting skills, a good understanding of and aptitude for technology, and an engaging leadership style.  In her role at Milestone, Ellen works closely with clients and fellow team members to leverage best-in-class technology tools to improve processes and drive efficiency. 

A refreshingly forward-thinking approach to the fundamentals

Accounting Services

Accounting services for everything your business needs to stay on track and plan for the future. Learn more about our Accounting Services.

HR Services

Your HR partner to manage everything from day-to-day programs to business-changing strategies. Learn more about our HR Services.

Payroll Services

The expertise you need to ensure timely and accurate payroll processing and a good employee experience.  Learn more about our Payroll Services

Get Started!

Transform your back-office into a competitive advantage.

Get in touch with a Milestone team member.