StartupExperts at Work

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

Field Guide, Volume 4

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!

Milestones, Renewal Reflections, and the Power of Community

From the desk of Jesse Freese

As we step into May, I’ve been reflecting on seasonal cadences that continue to shape my work and the community around me. Whether it’s celebrating community “wins” or helping teams navigate the complexities of renewal season, the lesson is clear: the more deeply we know and show up for people, the stronger our impact becomes.

What's happening in StartupExperts?


This month at StartupExperts we gained our 2,000 members and we’re rolling out new ways to connect and even more opportunities to learn, grow, and lead together. We announced our 25 Leaders to Follow in 2025 Program and are starting a Friday Forum Series. And AI Learning for Leaders…that continues too! 🚀

Guiding Resources

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

  • 2025 Venture Capital Benchmark Report (Affinity)

  • Sequoia’s 2025 Merit Cycle Trends (Sequoia)

  • HR to Employee Ratio: Benchmarking Guide [2025] (CompanySights)

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

Upcoming Events

May is packed with valuable opportunities to learn, recharge, and connect—whether you're tuning in online for practical sessions on networking, AI, and ethical tech use, or joining us in-person for energizing community events across Sacramento, NYC, and SoCal. A few highlights:

  • Beyond Handshakes: The Art of Strategic Networking for Growth & Opportunity – Thursday, May 8

  • AI Learning Journey: Ethical AI: Responsible Use in Everyday Operations – Wednesday, May 28

  • StartupExperts NYC Hub: AI & Data Privacy Workshop – Thursday, May 8

Guest Post: Navigating Leave with Care, Clarity, and Compliance

By: Ellen Kaster Porter, Head of Channel Sales at Sparrow

Whether it's welcoming a child, navigating a health crisis, or caring for a loved one—employees need clarity and care, not confusion and red tape. In this powerful piece from Sparrow, you'll hear firsthand why leave is one of the most human moments in the employee experience—and how companies can finally start managing it like it matters.

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