Club E Podcast: How to Hand Off an Entire Function, with Jennifer Libby

Ahead of the October 1 Club E luncheon, Rick Brimacomb sat down with Jennifer Libby, District Manager at Insperity, for a Club E podcast on a question every growing company eventually faces: how do you hand off an entire function? The conversation uses HR as the working example, but the lessons apply to any function an owner is thinking about moving outside the building.

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Key Takeaways

1. Handing Off Is Not Giving Up Control

Jennifer spent 25 years as an HR practitioner before joining Insperity, and she admits that when a close friend first pitched her on outsourcing, she shut him down without hearing him out. The fear was loss of control. What she learned on the other side: “You just get advice. You still make the decisions.”

2. It Is Not Just for Big Companies

Insperity works with companies from five employees up, and one of Jennifer’s first clients had exactly five. In Minnesota, their average client has 22 people. That five-person company was offered seven different medical plans, the kind of benefits a small team could never negotiate alone.

3. Start With the Basics, Then Prioritize

A hand-off usually starts with payroll, then the building blocks like handbooks and job descriptions. From there the owner and the provider prioritize together. How fast it moves depends on how much time the owner can give the transition.

4. Measure the Return in Three Buckets

Jennifer looks at the actual cost of what you spend today, the share of an owner’s or executive’s salary that goes to managing it, and the opportunity cost of what that time could have produced. Her sharpest question for owners: “Would you enthusiastically rehire everybody who works for you?” When the answer is no, that has a cost too.

5. The Hours Go Somewhere Better

What do owners do with the time they get back? Most put it into business development. Some get their company ready for sale sooner. And some, Jennifer says, finally get home in time to put their kids to bed.

6. Stay Curious

Her closing advice applies to any vendor in any function: talk to advisers who listen before they prescribe, and do not settle for “we’ve got it covered.” As she put it, the best companies “like their people and like to be profitable. They are not mutually exclusive.”

See It Live on October 1

The podcast covers the theory. On Thursday, October 1 at the Minneapolis Club, three Twin Cities operators share the moves that are actually working for them in Do More With Less: How to Operate in 2026:

• Sander Biehn – Founder and CEO of Ready For Social, and an Insperity client, on the function he handed off and what surprised him.

• John Arms – Founder of Voyageur University and author of Revolt, on the rise of fractional talent.

• Jessica Stone – Director of Operations at Irish Titan, on where headcount is essential and where process and tooling can carry the load.

Everyone in the room receives our detailed playbook notes after the event. Get your ticket here.

Club E is made possible by our sponsors: Insperity, Irish Titan, Breakthrough Impact Group, Highland Bank, Lab 651, and Recursive Awesome.