Milestone

Brenna Whitaker

Founder / VP – HR Services

A SHRM-SCP certified People Ops leader with 20+ years of HR experience, Brenna brings deep expertise in company culture, strategic HR, and organizational leadership.

brennawhitaker

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 the VP of People Ops at both mAccounting and inDinero.

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

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.

Youtube Video

HR Audit: Unlocking the potential in your HR function

Youtube Video

How Much Does It Cost to Outsource HR?

Youtube Video

How to choose the best payroll service for a small business

Youtube Video

What are the 7 functions of HR

Youtube Video

What HR Services Can Be Outsourced?

Youtube Video

Can I Do Payroll Myself For My Small Business?

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

Can a 501c3 have employees-

Can a 501c3 Have Employees?

Yes, a 501c3 can absolutely have paid employees, but tax-exempt status comes with specific IRS rules around compensation, worker classification, and payroll compliance that every nonprofit leader needs to understand before the first paycheck goes out.

What Is A Hostile Work Environment? Definition and 2026 Examples

Recognizing a hostile work environment isn’t always straightforward, especially when the signs are subtle or ongoing. This guide breaks down the legal definition and real world examples to help you identify and address the issue in 2026.

A 2026 Guide to Employee Relationship Management

Managing employee relationships well takes more than good intentions when teams are growing and priorities keep shifting. This guide covers the strategies and tools that help HR teams strengthen engagement and trust in 2026.

View Our Blog

Ready to transform your HR function?

Get executive-level HR guidance without the full-time cost. Let Brenna and the Milestone team become your people operations partner.

Schedule a Consultation Learn About HR Services