At WomenVenture, we believe that when one woman rises, we all rise. That belief is embodied by our volunteers—generous, mission-driven individuals who walk alongside our entrepreneurs, offering their time, insight, and support. During National Volunteer Week, we’re honored to share the story of Jill Lipski Cain—a mentor, expert advisor, and powerful force for connection.
Jill brings more than 15 years of experience spanning nonprofit evaluation, customer experience, and user-centered strategy, but it’s how she shows up—with intention, compassion, and clarity—that makes her impact truly special. When she launched her consulting firm, she made a commitment: to build pro bono service into the foundation of her work.
“I created space in my life to give,” she shared. “Volunteering was never an afterthought—it was part of how I wanted to structure my business from the start.”
For Jill, WomenVenture was the right fit from the beginning. Our mission aligned with her passion for creating meaningful opportunities for women to lead, build wealth, and design lives on their own terms. Through mentoring and expert advising, Jill has worked with a wide range of clients—from those just turning a lifelong passion into a business, to those scaling existing ventures—and she treats each session as a partnership.
What stands out most? The shared moments of clarity.
“Those lightbulb moments are everything,” Jill said. “It’s like being in a puzzle room together, and then we find the clue. That’s the magic.”
Jill’s approach blends empathy with practicality. She’s a supportive guide, a strategic thinker, and—most importantly—a trusted voice who reminds our clients that they can dream big and make smart decisions at the same time. Her volunteer work is also deeply reciprocal: “This has helped me sharpen my own skills, grow my network, and stay grounded in why I do what I do.”
When asked what she’d tell someone considering volunteering, Jill didn’t hesitate:
“Start with what you know, and lead with what brings you joy. Volunteering can be a way to grow—professionally and personally. It’s not about having all the answers; it’s about showing up with intention and helping someone take the next step.”
Her favorite reminder, posted above her desk, sums it up best:
“I can create the life I want despite uncertainty.”
Jill is doing just that—and helping others do the same.
To Jill, and to every volunteer who gives their time and heart to WomenVenture: thank you. Your contributions help our entrepreneurs move forward with understanding, confidence, clarity. The difference you make doesn’t end with a single session—it lives on in the businesses our clients build, the jobs they create, and the communities they impact.
Author: Kiara Hollie-Sessions, WomenVenture Marketing Specialist
Help us continue this vital work.
Consider how you can make an impact today.
Volunteer with us and share your expertise with emerging entrepreneurs. Learn more about volunteering with WomenVenture.
Make a donation to WomenVenture to ensure women entrepreneurs have access to the programs and resources needed for success.
Your involvement helps fuel the future of women’s entrepreneurship.
