Navigating Capital As A Woman: Stephanie Jones Of It Takes a Village (iTAV) Software & Services On Top Strategies for Women Founders, CEOs and Leaders Seeking Institutional Investments
An Interview with Vanessa Ogle
Know your customers’ pain points and solve one problem at a time. Build and test a prototype quickly.
When I incorporated my business in March 2025, I devoted the first 90 days exclusively to research. I engaged more than 75 industry experts, attended intimate conferences, and partnered with a market research firm to conduct live focus groups with prospective customers — all fueled by relentless curiosity. I also published expert interviews as LinkedIn columns to spotlight critical industry challenges. With over three decades of experience in government-sponsored healthcare, I had an initial sense of the problem I wanted to solve, but I didn’t assume I was right — I validated it and stayed open to discovering new ones. By day 91, we had begun building our demo prototype, which was completed within 30 days. Within a week of completion, we had eleven virtual demos scheduled, and by the second week secured two verbal commitments from prospective customers to participate as early design beta partners. This upfront investment in research, validation, and relationship-building paid immediate dividends once our demo prototype was ready to market.
Despite making remarkable strides in the business world, women continue to face unique challenges when seeking institutional investment. In this series we would like to discuss the process of securing capital from institutional investors, and provide actionable strategies to help women founders, CEOs, and leaders navigate this critical aspect of business growth successfully. I had the pleasure of interviewing Stephanie Jones.
Stephanie Jones is a healthcare technology executive with over 30 years of leadership experience with a focus on operations and customer success. She has held senior roles at organizations such as UnitedHealth Group and Aetna and played a pivotal role in scaling Convey Health Solutions, helping take the company public. In 2025, she founded It Takes a Village (iTAV) Software & Services to simplify healthcare and advocate for underserved populations, while also continuing her work as an author, thought leader, and philanthropist.
Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
I began my career in healthcare right out of college. With a bachelor’s degree in Business Administration, my options were broad, and back in the 1990s, job searches were done through the newspaper. I applied to every entry-level professional role I qualified for, and Cigna Dental was hiring Account Analysts with full training provided. I got the job, and thirty-three years later, I’m still in healthcare and haven’t looked back.
Can you share the most interesting story that happened to you since you began your career?
There are so many memorable moments but ringing the bell at the NYSE for Convey Health Solutions (CNVY) in 2021 was a true highlight. After more than 15 years with the company, standing on the balcony celebrating with my colleagues brought back every milestone we had achieved together. It’s a moment I’ll never forget.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
Reaching the C-Suite of corporate America came with certain privileges — budgets for travel, easy access to attorneys, and large teams of resources. When I transitioned to a bootstrapped sole founder role, I learned the hard way that I couldn’t email my law firm with every question. The first invoice was a wake-up call. It took a few months, but I learned to prioritize what was truly important before hitting ‘send’.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
So many people took chances on me, but the first stands out most. My second manager at Cigna Dental, Suzanne Prowse, left to take a bigger role at a growing health plan. I was the first person she called to help build their product development organization from scratch. At the time, I had no medical benefits or product development experience, so her faith in me was transformative. That leap gave me the confidence to rise through my career and eventually lead a $400M P&L as Chief Operating Officer.
Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?
In 2021, after our adult sons moved across the country post-COVID, my husband and I became empty nesters overnight. It made me question all the dreams I had put off. Then I read The Year of Yes by Shonda Rhimes. This book pushed me to stop waiting and start doing. I credit The Year of Yes with motivating me to publish my own memoir and for founding iTAV.
How have you used your success to make the world a better place?
Leadership isn’t easy, and I’ve had to make tough decisions that impacted people’s lives. But I’ve always tried to stay humble and human. My husband and I intentionally support charities focused on children and young adults, and my greatest joy is being a mother, mentor, and example to my family. Watching my sons, nieces, and nephews thrive, I feel proud knowing I’ve played a role in influencing their paths.
What do you think needs to change in the investment landscape to support more women entrepreneurs?
The industry needs more willingness to get uncomfortable and break norms. Greater diversity of thought and practical experience in boardrooms and VC/PE firms would expand perspectives on what makes a successful leader. Right now, investors rarely face risks or consequences for betting on young Ivy League founders, yet women-led businesses — proven more successful in studies — still receive less than 3% of capital. That must change.
Can you share a defining moment in your journey to secure institutional investment? What was a key lesson you learned from that experience that other women can apply in their funding efforts?
After two decades in PE-led portfolio companies, I had built strong relationships with investors. When I founded iTAV, many of those leaders took my calls, gave advice, and even reviewed my prototype. I wasn’t afraid to reach out, and the response has been overwhelmingly supportive. I learned that people want to know what you’re building — you just have to ask. Confidence, paired with expertise, goes a long way.
In your experience, what key factors do institutional investors look for in women-led startups that may differ from their general investment criteria?
Investors want proven experience, authenticity, passion, and a strong grasp of the problem you’re solving — just as much as they want to see your numbers. I recommend women CEOs lead with both head and heart. Remember, you’re also interviewing investors to ensure they’re the right partners for your journey.
How do you build and leverage networks to gain access to institutional investors interested in supporting women-led businesses?
Start with one founder you know — ideally someone who’s successfully raised capital. I research companies on Crunchbase or other publicly available sources to understand their funding and investor history before making connections. And I never hesitate to share what I’m building, even with competitors. By setting up quick calls with friends, former colleagues, and other founders, I’ve gotten warm introductions to investors. Be bold, speak up, and let people in on your vision.
How have you navigated the negotiation process with institutional investors to ensure fair valuation and terms for your company?
I’m still bootstrapping by choice, but I’ve been deliberate about building investor relationships. My advice is to secure a top-notch legal team early. I’m investing in lawyers with deep expertise in M&A and patents because I see this as the long game. Laying the right foundation now will protect the business when negotiations begin.
Can you please share your “Top 5 Strategies for Women Founders, CEOs and Leaders Seeking Institutional Investments”?
1. Know your customers’ pain points and solve one problem at a time. Build and test a prototype quickly.
When I incorporated my business in March 2025, I devoted the first 90 days exclusively to research. I engaged more than 75 industry experts, attended intimate conferences, and partnered with a market research firm to conduct live focus groups with prospective customers — all fueled by relentless curiosity. I also published expert interviews as LinkedIn columns to spotlight critical industry challenges. With over three decades of experience in government-sponsored healthcare, I had an initial sense of the problem I wanted to solve, but I didn’t assume I was right — I validated it and stayed open to discovering new ones. By day 91, we had begun building our demo prototype, which was completed within 30 days. Within a week of completion, we had eleven virtual demos scheduled, and by the second week secured two verbal commitments from prospective customers to participate as early design beta partners. This upfront investment in research, validation, and relationship-building paid immediate dividends once our demo prototype was ready to market.
2. Involve customers early in product development. Secure beta partners and LOIs before seeking capital if possible.
My first product vision lived in a simple PowerPoint deck. I iterated on it constantly and wasn’t shy about sharing it, even when it wasn’t perfect. My goal was to validate the problem, not present a polished pitch. At conferences, I’d open my laptop during lunch and ask industry leaders for feedback. Not once did someone refuse. Those early conversations became the foundation of my beta partner pipeline — the same people I later invited to review my prototype. Before investing in a minimum viable commercial product, I set a goal of securing two to three beta design partners with signed letters of intent to help shape and test the solution.
3. Share real-life stories about the problem you’re solving so your message resonates with both investors and clients.
I’ve never loved formal presentations, but I thrive in authentic conversations. Early on, I worried about investor pitches, until my mentor and advisor, Rodney Adkins — an experienced investor himself — reminded me that investors want authenticity and passion. That changed everything. I now focus on building organic relationships through warm introductions, often starting with casual “get to know you” calls. These conversations allow me to share the real stories behind the problem I’m solving, add a human element, and educate investors on the industry. Even though I’ve bootstrapped so far and haven’t formally pitched, I’ve built strong investor relationships this way. My client conversations are handled in a similar manner — I focus on understanding their challenges and I bring a genuine authenticity to helping them solve them.
4. Surround yourself with strong teammates or fractional consultants. Don’t try to do it all — delegate where you can.
Delegation comes naturally to me from my years as a corporate executive. As a founder, I focus on what only I can do: vision, relationships, and sales. For everything else, I rely on talented fractional consultants from my network. Many are full-time independents who generously adjusted their rates to work within my budget. I chose to pay for their services rather than give up equity too early, which I highly recommend if possible. This approach has allowed me to build a capable team without diluting ownership.
5. Start with the end in mind. Know your exit strategy, as it will guide which investors align best with your vision.
One of the best pieces of advice I received came from Keith Pigues, Founder and CEO of Luminas Strategy: “Start with the end in mind.” He encouraged me to define my exit strategy early, as it shapes which investors are the right fit. He also reminded me not to shy away from competitors — in fact, they can become future investors, acquirers, or even partners.
I’ve taken that advice to heart, building referral partnerships with companies whose solutions complement mine. When they succeed, I succeed. At a workforce management conference, for example, I met Spencer O’Leary, Managing Director of ActiveOps USA — a company others might have seen as a competitor. Instead of avoiding the conversation, I explored their product and found real value in what they offered — value that my product wasn’t designed to address. I even directed several attendees to their booth. That decision turned into a lasting relationship: ActiveOps is now a strategic partner for iTAV, and I serve on their advisory board to support their expansion into North America.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
If I could inspire a movement, it would be to make healthcare simpler, more transparent, and more equitable for all. Too many people — especially in underserved communities — struggle to access the care they need because the system is fragmented and confusing. Through technology, workforce innovation, and advocacy, we can create a healthcare system that works for everyone, not just a select few.
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.
I would love to have a private breakfast or lunch with Mellody Hobson, CEO of Ariel Investments. Mellody is known for her candor and authenticity in conversations about race, gender, and equity. I aspire to bring that same level of honesty and courage into my own leadership and investor relationships.
How can our readers further follow your work online?
I am easily accessible on LinkedIn.
www.linkedin.com/in/stephaniejones-itav-healthtech-founder
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
About The Interviewer: Vanessa Ogle is a mom, entrepreneur, inventor, writer, and singer/songwriter. Vanessa’s talent in building world-class leadership teams focused on diversity, a culture of service, and innovation through inclusion allowed her to be one of the most acclaimed Latina CEO’s in the last 30 years. She collaborated with the world’s leading technology and content companies such as Netflix, Amazon, HBO, and Broadcom to bring innovative solutions to travelers and hotels around the world. Vanessa is the lead inventor on 120+ U.S. Patents. Accolades include: FAST 100, Entrepreneur 360 Best Companies, Inc. 500 and then another six times on the Inc. 5000. Vanessa was personally honored with Inc. 100 Female Founder’s Award, Ernst and Young’s Entrepreneur of the Year Award, and Enterprising Women of the Year among others. Vanessa now spends her time sharing stories to inspire and give hope through articles, speaking engagements and music. In her spare time she writes and plays music in the Amazon best selling new band HigherHill, teaches surfing clinics, trains dogs, and cheers on her children.
Please connect with Vanessa here on linkedin and subscribe to her newsletter Unplugged as well as follow her on Substack, Instagram, Facebook, and X and of course on her website VanessaOgle.
Navigating Capital As A Woman: Stephanie Jones Of It Takes a Village (iTAV) Software & Services On… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.