Melissa Stout
Founder / VP – Operations
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.
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’s degree, Accounting and Marketing
Indiana University – Kelley School of Business
Bloomington, IN
Certified Public Accountant
State of Indiana
Video Content
Watch Brenna share expert perspective on HR strategy, compliance, and people operations.
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 Melissa
View Our Blog
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