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

small business owner calculating payroll and expenses using calculator and laptop

Can I Do Payroll Myself for My Small Business in 2026?

Yes, you can do payroll yourself for your small business, but whether you should depends on how much time you have, how much compliance risk you can tolerate, and whether you know about the three payroll rule changes that make 2026 different from every year before it.

Average payroll cost per month

Average Payroll Cost Per Month in 2026

Before you commit to a payroll service, here is the straight answer most providers do not want you to see: what small businesses actually pay per month in 2026, what drives that number up, and where the hidden fees are buried.

employees talking about startup employee benefits

A Guide to Employee Benefits for Startups

A competitive benefits package does not require a large-company budget, but it does require knowing what candidates actually expect, what you are legally required to offer, and how to build something sustainable before the compliance gaps quietly grow into real problems.

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