A smiling woman with shoulder-length dark hair looks at the camera. She is wearing a sleeveless purple patterned top, gold hoop earrings, and layered gold necklaces. The background appears to be an indoor event space with neutral-colored walls and stacked chairs.

Jess Skylar

Fundraising + Exec Coaching

Jess has spent her career growing + scaling non-profit AND for-profit social ventures – think Revolution Foods from $14M to $170M and Think of Us from $700K to $15M!

Connect w/ Jess

Your Partner in How

  • Scaling mission-driven organizations without losing the mission
  • Having the hard conversations that move things forward
  • Hands-on-keyboard strategic and operational support

What People Say about Jess’s Work


“Jess played a key role in Revolution Foods’ growth from $14M to $170M. She combined operational excellence with unwavering commitment to our mission, helping us expand healthy food access while building sustainable systems. Her strategic thinking and hands-on leadership style were crucial to our national expansion.”

– Kristin Richmond, Founder, Revolution Foods

“Jess was instrumental in turning HIP’s vision into reality. She built the operational foundation that allowed us to scale while developing frameworks that helped shape the impact investing industry. Jess’s ability to balance mission with practical execution was exactly what we needed in our early days, which still are impactful today.” 
– R. Paul Herman, CEO + Founder, HIP Investor

“Before working with Jess, I was exhausted and overwhelmed. Now I feel like I have this magic resource in my back pocket—a true partner who can help turn complexity into clarity while keeping our heart at the center.”
— Helen Leung, Executive Director, LA Más

Why Helia LOVES Jess

Well, I created Helia so this is a bit awkward! Jess is a doer through and through – and bring years of experience learning (with all the successes and the failures) with a network of beautiful humans who share their wisdom and have taught her so much of what she gets to know.

Jess’ finds joy + ease in

Sitting in my yard, reading in my hammock, hiking with my pups, water (drinking/swimming/floating/kayaking), writing

Get in Touch

Jess in the Helia Library

Resource Toolkit Jess’s Reach Out Anyway Toolkit Everything you need to make the ask — from the email you've been sitting on for three weeks, to the seven-month job search that turns into a network-building practice.
Helia with Helia
Resource Toolkit Jess’s Honest Transitions Toolkit Everything you need to navigate the hardest people conversations — from the moment you know it's time to the email that tells your team.
Jess Skylar with Jess Skylar
Resource Toolkit The Discovery360 Toolkit Everything you need to hear what's really happening in your organization — and do something about it.
Helia with Helia
Resource Toolkit Helia’s Fundraise From Your Strengths Toolkit The planning guide and campaign tools that help you build a fundraising plan you'll actually use.
Helia with Helia
Article Fundraise From Your Strengths On why the best fundraising plan starts with what you're already great at — and builds from there
Natalie Bergstrasser with Natalie Bergstrasser
Article Your People Already Know The Discovery360: a strengths-based approach to finding out what's really happening in your organization
Helia with Helia
Article When It’s Time for Someone to Go Scripts and strategies for the hardest conversations
Helia with Helia
Resource Toolkit Jess’s Right Hire Toolkit Stop writing job descriptions. Start with the questions that actually prevent a mis-hire.
Helia with Helia
Article An Interview Process Where Everyone Says HELL YES You Know Who You Need. Here's How to Actually Find Them.
Helia with Helia
Article The Right Role at the Right Level Why Your Last Hire Didn't Work Out (And How to Get It Right Next Time)
Helia with Helia
Resource Toolkit Jess’s Interviewing Toolkit Everything you need to stop hiring the wrong people — and start finding the ones who'll actually thrive.
Helia with Helia
Article Different Cultures Need Different Humans Get Honest About Your Culture Before You Interview Anyone
Helia with Helia