StartupExperts at Work

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

Field Guide, Volume 3

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!

Transform Takeaways, Benefit Renewals, and HR Plot Twists

From the desk of Jesse Freese

Transform never disappoints—except maybe when you catch Covid.
Still, the energy, the people, and the conversations made it worth it. I’m thinking more than ever about how we can create better opportunities for learning and meaningful interactions.

What's happening in StartupExperts?

Big things are happening across the StartupExperts community!
From a powerful showing at Transform 2025 to buzzing local meetups, an AI learning journey, and our March Book Club wrap-up, this community is growing fast. We’re spotlighting new programs, launching a fresh new look, and building even more ways for members to connect and grow.

Guiding Resources

Must-Reads & Thought-Provoking Insights This Month

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

-2025 Retention-Focused Compensation & Equity Trends (Sequoia)

-The State of Employee Leave: Sparrow’s Benchmark Report (2025 Edition)

-H2 2024 State of Startup Compensation (Carta)

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

April is packed with valuable opportunities to learn, recharge, and connect—whether you're tuning in online for practical sessions on confidence, KPIs, or AI adoption, or joining us in-person for moments of wellness and community. These events are designed to support you as a leader, connect you with peers, and keep you ahead of what’s next.

A few highlights:

  • Confidence Accelerator | How to Trust Yourself to Deliver Authentically – Friday, April 11

  • Tracking KPIs (Reporting & Analytics) – Tuesday, April 22

  • AI Learning Journey: Driving AI Adoption: Build Buy-In and Avoid Pitfalls – Wednesday, April 30

Click below to explore all the upcoming events and register now!

Guest Post: Why I Keep Coming Back to Transform

By: Holly Hatlo, Lead HRBP at Hatch

Holly Hatlo shared why the Transform conference has become a can’t-miss event in her calendar. Now five years in, Holly emphasizes that it’s not just the content that keeps her coming back—it’s the people.

Her takeaway? The most valuable part of any conference is the connection. Volunteering, supporting peers, and creating space for meaningful conversations have made the experience deeply rewarding. As Holly puts it: embrace the FOMO, prioritize people, take breaks, and show up ready to give. You’ll walk away with so much more.

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