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Scaling a business is messy. Doing it while managing HR, payroll, and compliance from a distance? Even messier.

In this episode, Macy Ewing—CEO of Aaronson Group—joins us live from isolved Connect in Chicago to talk about her transition from truck insurance underwriter to leading operations for a rapidly growing virtual company. From paper-based retirement plans to compliance thresholds that come with scaling past 50 employees, Macy shares the real challenges behind small business HR.

We get into what it means to meet people where they are, why saying no is a leadership skill, and how digital transformation (even as simple as switching from checks to 401K integrations) changes everything for small teams.

Timestamps:

00:00 — Meet Macy Ewing, CEO of Aaronson Group

01:00 — From underwriting to virtual operations

02:39 — HR priorities vs. entrepreneurial urgency

04:09 — Scaling people while staying compliant

06:05 — Learning through audits and external perspective

08:04 — 401K win: ditching paper for payroll integration

10:11 — Let experts be experts: the power of partnership

12:41 — What being a People Hero really means

13:24 — Meeting employees where they are (literally and digitally)

16:51 — Communication skills, generational gaps, and teachable moments

19:05 — Recharge strategy: the discipline of saying no

21:07 — Empowerment through boundaries and mistakes


This conversation was recorded live at isolved Connect in Chicago.

The Heroes of HR podcast is a limited series sponsored by isolved. isolved is an HCM platform that modernizes HR, benefits, and payroll across Healthcare, Hospitality, Manufacturing, and more.

You can learn more about isolved here: https://www.isolvedhcm.com/


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