A Field Guide about the Workplace, its Leaders, and Becoming Better.

I'm excited to share with you knowledge, resources, and cool things that I've encountered with a focus on helping us all become better as leaders. My intention is that this will not be another monthly newsletter but rather a "Field Guide" that will help you improve your work product and give you actionable data and resources that can be immediately applied. We will be refining as we go so feedback, suggestions, and contributions are more than welcome. Enjoy!

From the desk of Jesse Freese

The PEO model has long been one of the most effective ways for fast-growing startups to manage HR, payroll, compliance, and benefits — especially when 75% of company spend is tied to its people. But as this section outlines, the industry is facing a serious credibility challenge fueled by artificially low premiums, aggressive client-acquisition tactics, and tech-first PEOs underpricing risk to win deals.

This piece is a call for greater transparency, accountability, and long-term thinking across the PEO industry — because when trust breaks, startups and their employees pay the price.

The StartupExperts community is closing out the year with incredible momentum — from hosting 10+ in-person and virtual events this month, to welcoming a new cohort of members, to continuing our AI Learning Journey as we head into its final session on December 17th. We also celebrated key leadership transitions, welcomed new team members, and continue to build on the success of our Becoming Better with StartupExperts podcast series featuring our 25 Leaders to Follow in 2025.

It’s been a season of connection, learning, and community growth — and the energy only continues to build as we move toward year-end. Stay connected, jump in, and see what’s ahead. 🚀

Here’s a quick rundown of interesting reads and insights we found valuable this month:

Plus, we’re spotlighting a few standout community members making an impact—you’ll definitely want to meet them and follow their work!

We’re closing out the year with a powerful mix of learning, connection, and celebration. From our annual NYC Holiday Party to hands-on workshops and a members-only Book Club, December is packed with opportunities to grow, reflect, and get ready for 2026. Here’s a quick view of what’s ahead:

By: Justin Clifford, Co-Founder at Bereave

This month, we sat down with Justin from Bereave to explore why supporting employees through grief is both a human responsibility and a business imperative. Most managers want to show up well during moments of loss—but few feel equipped. Bereave exists to bridge that gap, giving employees real-time guidance and providing HR and managers with a clear, compassionate playbook.

Bereave helps teams respond with consistency and care through:

The result: employees feel supported rather than isolated, and organizations build trust and stability where it matters most.