StartupExperts at Work

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

Field Guide, Volume 9

Welcome to Volume One of the 2026 StartupExperts at Work Field Guide — a practical resource for navigating the workplace, leading with intention, and becoming better at what we do. This isn’t a traditional newsletter. It’s a curated Field Guide designed to share ideas, tools, and resources you can actually use in your work right now. We’ll continue refining it as we go, so feedback and contributions are always welcome.

Here’s to learning, experimenting, and building better together in 2026.

Welcome to 2026

From the desk of Jesse Freese

As we head into 2026, I’ve been thinking a lot about what actually makes a community work — and why StartupExperts continues to thrive. This year, after much leadership discussion, we’re doubling down on encouraging greater participation and working to discourage simply consuming. It’s one of the reason why we are buying 90+ copies of Priya Parker’s great book called “The Art of Gathering” for our entire all-volunteer leadership team.

Read more as I share the two priorities guiding StartupExperts in 2026 and I make a simple ask of every member. This is going to be a great year.

What's happening in StartupExperts?

The community kicks off 2026 with strong momentum, celebrating its eighth year as a trusted, member-led group. From surpassing 2,400 members and expanding into new global chapters, to hosting 120+ events and deepening partnerships that support the work, this update reflects on how far the community has come — and what we’re excited to build together in the year ahead.

At the heart of it all is participation. Powered by volunteer leaders, member referrals, and a shared Go-Giver mindset, StartupExperts continues to grow through trust, contribution, and connection. As new programs launch and partnerships expand, the community enters 2026 grounded in its values and energized by what’s ahead.

Guiding Resources

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

  • 6 HR Predictions for 2026 (Camille Hogg, Lattice)

  • Why Lean Teams are Turning to Outsourcing for Compensation & Benefits (Sequoia, Compensations Team)

  • HR Trends to Watch in 2026 (By: Korn Ferry)

Plus, we’re spotlighting a few standout community members making an impact—you’ll definitely want to meet Elizabeth Woodfield and Sophie Barbier!

Upcoming Events

We’re kicking off 2026 with a powerful mix of learning, connection, and momentum across the StartupExperts community. From thought-provoking online sessions on AI and leadership, to members-only forums and book clubs, to in-person dinners and gatherings across the U.S., the weeks ahead are packed with opportunities to learn, connect with peers, and go deeper together.

Whether you’re joining us online, showing up locally, or supporting our partner events, there’s no shortage of ways to engage, reflect, and build meaningful relationships as we head into the year. Here’s a snapshot of what’s coming up:

  • Breakfast Table Talk, NYC — February 5th

  • Happy Hour, Oakland — February 5th

  • HR Leaders Dinner — February 26th

Guest Post: The Real Risk — Single Points of Failure Don’t Scale

By: Nicole Gunara, Principal Immigration Attorney at Manifest Law

In this guest post, Nicole Gunara, Principal Immigration Attorney at Manifest Law, one of StartupExperts’ newest community partners, explores why single points of failure — particularly in immigration strategy — create hidden risk for growing organizations. Drawing from her work with founders and operators, Nicole makes the case for designing talent systems with flexibility, optionality, and resilience in mind, offering a timely perspective for leaders navigating an increasingly unpredictable global hiring landscape.

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