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.

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

as seen in

Recent Posts by Brenna

The 20 Best Payroll Management Software Options in 2026

With dozens of payroll platforms on the market, finding the right fit for your business can feel overwhelming. Milestone rounds up the 20 best payroll management software options in 2026 to simplify your search.

What Is a Payroll Management System? A 2026 Guide for Businesses

Manual payroll processes can lead to costly errors and compliance headaches as a business grows. Milestone breaks down what a payroll management system does and how to choose the right one in 2026.

What Are Workplace Documentation Best Practices for HR in 2026?

Poor documentation can leave HR teams exposed during disputes, audits, or terminations, turning small issues into costly liabilities. This guide covers workplace documentation best practices for 2026, helping HR professionals protect their organizations and stay compliant.

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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.