Brenna Whitaker
Founder / VP – HR Services
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 the VP of People Ops at both mAccounting and inDinero.
Brenna is a graduate of Indiana State University and a SHRM Senior Certified Professional.
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 Science, Human Resources and Business Administration”
Indiana State University
Terre Haute, IN
“Senior-Level Certification Recognizing Mastery of the Strategic and Policy-Making Aspects of HR Management”
SHRM Senior Certified Professional
SHRM-SCP | Society for Human Resource Management
HR Audit: Unlocking the potential in your HR function
This video is part of a video series where Brenna, our HR leader, helps small business owners unravel the complexities of HR so they can focus on building the business of their dreams without the headaches. In this video we talk about HR Audits.
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 Brenna
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