Board of Directors

Jim Stallings is an internationally recognized business leader, entrepreneur and investor who specializes in launching and scaling early stage companies in areas of technology and ecommerce. Jim is the Founder and CEO of PS27 Ventures and has been involved in starting dozens of new ventures in FinTech, HealthTech and Software as a Service.

He believes innovation should be viewed as the core offensive strategy of any company, "either disrupt or be disrupted". Jim's career spans over 30 years as IBM General Manager of several major lines of business including the company's $7B Linux software business, its intellectual property division with 39,000 patents and its $21B global hardware sales group. He started his business career as a data analyst in the Space Division at GE.  

Jim earned a Bachelor of Science degree from the US Naval Academy and served as a Captain in the US Marine Corps. He is on the Board of Directors at Fidelity National Informations Systems (FIS), UGI Corporation (UGI) and Cannae Holdings, Inc (CNNE). He also serves as a Trustee on the Folded Flag Foundation which provide scholarships to descendants of fallen warriors in the US Military.

Annie DeStefano is Vice President, FIS Banking Solutions, leading ecosystem partnerships and the FIS Accelerator programs. She was previously a Director in Silicon Valley Bank’s product and global payments division, leading partnerships, and a commercial bank director for the national fintech banking team. In her role she worked closely with entrepreneurs, investors, and influencers across the national fintech ecosystem.

Prior to SVB, she held roles in engineering, product management and operations at venture-backed location intelligence company Foursquare and investment bank Goldman Sachs, as a member of the launch team for the Marcus by Goldman Sachs consumer banking platform.

In 2019, she was named an "Inspiring Fintech Female" by the NYC Fintech Women organization and in 2021, a ’40 Under 40’ recipient by her alma mater, Stevens Institute of Technology. She is active in fundraising for the National Ovarian Cancer Coalition and recently received certification as a habit coach. She served as a member of the Stevens School of Business Board of Advisors and currently sits on the University of North Florida College of Computing, Engineering, and Construction Dean’s Leadership Council.

Caleb Garrett serves as the Director of Development at the University of North Florida’s College of Computing, Engineering & Construction. In this role, he oversees fundraising and external engagement initiatives involving the college's donors, alumni, and business partners. Under his guidance, the college has achieved unprecedented success in fundraising, setting a record for the amount of support garnered during his tenure. Caleb has also played a pivotal role in rekindling connections between alumni and the university. Prior to joining UNF, he worked in local nonprofits and taught in the public school system.

Caleb holds a Bachelor’s Degree and a Master of Divinity from Palm Beach Atlantic University, along with a Certificate in Fundraising Management from the Lily Family School of Philanthropy at Indiana University. In addition to his service on the PS27 Foundation Board, Caleb is a member of the board of the Youth Crisis Center and actively volunteers at his local church.

Demika Jackson has over 20 years of experience in nonprofit management, military operations, training, and development. She is a proud U.S. Army Veteran whose dedication to serving others led her to establish ReInVentU, L.L.C. in 2019, where she currently serves as the Founder and Chief Executive Officer, helping organizations reach their full potential through nonprofit management and professional development.

Demika is a dynamic individual known for her leadership and passion for positively impacting her community. As the President and Founder of Jacksonville Veterans Chamber of Commerce, Inc. since 2020, she has spearheaded initiatives to support and empower fellow veterans in the business world. With vital advocacy work and a diverse background, Demika's expertise is evident in her previous roles as P.E.A.C.E. Program Manager at Volunteers in Medicine and Prevention Coordinator at L.S.F. Health Systems and Clinical Program Coordinator at Community Rehabilitation Center, Inc. She has experience as a Dean of Students in middle and high schools, as an S.A.R.C. (Sexual Assault Response Coordinator), and as a S.H.A.R.P. (Sexual Harassment/Assault Response and Prevention) Consultant for an International Mobile Training Team.

She continues to expand her knowledge with ongoing education - currently pursuing a master’s in business administration, a master’s in psychology, and certification for Project Management. She also holds a Bachelor of Arts degree in Psychology from Armstrong Atlantic State University. In addition to her work with veterans' organizations, she serves as Chair for the Mayor's Commission on the Status of Women and the Mayor's Hispanic American Advisory Board. Her involvement with Zeta Phi Beta Sorority, Inc., The Mission Continues, and other meaningful causes showcases her dedication to creating positive change.

Through her various roles and experiences, Demika is committed to empowering women and military veterans through education, community, entrepreneurship, and advocacy. Her determination, resilience, and compassion make her a true inspiration and trailblazer in her field.

Heather Horovitz serves as the SVP, CDFI & Impact Lending for VyStar Credit Union. In this role Heather combines her 12 plus years of finance and management experience with a passion for community development and outreach. She collaborates with internal teams and outside partners to meet the unique needs of distressed neighborhoods with the mission of improving access to capital for low and medium-income people, contribute to generational wealth building, and driving projects that have positive community outcomes.  

Prior to her time at VyStar and in the financial industry, Heather worked in the food and beverage industry as a chef. She credits her time as an Executive Chef for her ability to manage large teams under stressful conditions. After her time in the kitchen and earning two graduate degrees from Florida International University in Miami, FL, she transitioned to the financial world, working in various finance and operations roles and eventually in corporate development (M&A) and strategic planning. 

Born and raised in the Bahamas, Heather has a unique talent of connecting with people. She leverages her diverse background to engage in the community and develop financial products and programs that are affordable and approachable for all people.

In addition to her professional role, Heather has a passion for serving the community. She is a board member for the North Florida School of Special Education and serves on the Finance Committee. In 2022, Heather was appointed by Mayor Lenny Curry to the Jacksonville Housing Authority as a Commissioner. She chairs both the Acquisition and Finance committees. In this role she advocates for housing inventory and access. She is a member of the Mayors Youth At Work steering committee which works to address workforce development for Jacksonville Youth. 

Heather is a 2023 Jacksonville Business Journal 40 under 40 honoree. 

Heather has a passion for health and wellness. In her free time, she trains for long-distance triathlons and marathons. She enjoys coaching people to reach their fitness as well as professional goals and is an active mentor. She is also a youth athletics coach and enjoys helping student athletes develop technical and personal skills on the field. She is a proud swim and baseball mom.

Laurence Andrews is currently serving as the Coordinator and Business Manager for Santa Fe College’s Center for Innovation and Economic Development (CIED) – a business incubator. Prior to this he was the Program Coordinator for the Bradford County Incubator – a collaborative entrepreneurship training program between the CIED and CareerSource North Central Florida.

The goal of that program was to help local entrepreneurs turn their ideas into income. Laurence has over 20 years of experience analyzing problems and providing strategic and innovative solutions for clients and coworkers in the public and private sectors.

Laurence has an MBA with a focus on Strategy Development and Entrepreneurship from Babson College and an interdisciplinary BS in Business Administration and Music from Alliance University/Nyack College. He also holds Certificates of Completion from the University of St. Gallen Switzerland’s International Study Program (ISP) – a 10-week intensive study exchange program focusing on doing business in continental Europe, the Price-Babson Symposium for Entrepreneurship Educators – a weeklong immersive program focusing on Action-Based teaching methods for entrepreneurship educators and incubator managers, and the International Business Innovation Association (InBIA) in Entrepreneurship Center Management.

Neal G. Anderson has been a leader and expert in the FinTech Business to Business payment automation sector for over 35 years. As president and CEO, he led OnPay Solutions from startup in 2009 to Exit in 2022.

OnPay Solutions focused on achieving its mission of impowering people to improve the lives of accounting departments, Globally. OnPay Solutions’ flagship product, OnPayConnect, allowed mid-size to enterprise clients to pay their vendor invoices electronically. First released in 2017, OnPayConnect processed $178 million dollars of Accounts Payable spend. In 2023, that dollar amount grew to $22 Billion. Customers who trusted OnPay Solutions to process their payments included UHaul, Trader Joes, AIG, Suddath, Sedanos Grocery and Booz Allen.

This success resulted in the acquisition of OnPay Solutions by Stockholm Sweden based Medius Software in March of 2022. Neal has held leadership positions as CEO at Payformance and Senior VP and General Manager at Sungard. Today, Neal serves on several advisory and corporate boards of directors.

Sang Cho is currently the Co-founder, President, and CFO of Rounded, by Concealment Express a manufacturing company, and Co-founder and President of Haymaker Coffee Company both based in Jacksonville, Florida.

Beforehand, he lived in Houston for seven years working with NexTier Inc, formerly Keane Group, working directly with the COO and CFO to build the infrastructure and team to position it for IPO, which went public in 2017. Prior to Keane Group, Sang began his career with GE, progressing through the Financial Management Program and continuing on through their Global leadership program, the Corporate Audit Staff. Through his rotations, he lived and worked in Belgium, Germany, Japan, Norway, and the UK among others.

Sang is a member of the Young Presidents’ Organization (YPO), former Chair, and a Founding Board Member of Bloom Academy, a charter school in Houston, Texas, a graduate of the Leadership Jacksonville Program, a fellow of NetKAL X, and American Leadership Forum of Houston, Texas.

Sang earned a M.P.A. from the John F. Kennedy School of Government at Harvard University, a M.B.A. from the Kellogg School of Management at the Northwestern University, and a Bachelors of Business Administration at University of Miami.

Megan Hayward's entrepreneurial spirit and passion for innovation sparked her desire to transform the outdated processes of blue collar temporary staffing. Her frustration with the status quo motivated her to launch her own staffing agency at a young age, then driven by the belief that the industry was ready for a radical change, she began to create a software platform to allow for a modern approach to an antiquated industry.

Megan founded her first staffing agency at the age of 24 after being a co-founder of another. Her achievements in the industry have earned her a seat on the advisory board of the latter. She is a member of the 2023 class for Leadership Florida, 2024 Hightower Fellow, and 2024 Leadership Florida Connect class member. 

Megan's dynamic personality extends beyond her professional pursuits as she also boasts an adventurous side with a penchant for adrenaline-inducing activities including wing walking on planes. Her love for fantasy books showcases her imaginative and creative mind, indicative of her innovative approach to her work. Megan competitive spirit was the force behind her obtaining a Division I basketball scholarship at the University of North Florida, and after graduation she was on stage in fitness competitions - even landing her a spot on season 1 of Steve Austin's Broken Skull Challenge (episode 8 if you have nothing but free time).

Megan is still involved in local sports as she is the one of the owners of the Jacksonville Icemen, the Community First Igloo, the Savannah Ghost Pirates, and the Allen Americans. 

Despite her numerous accomplishments, Megan prioritizes her role as a mother to Israel and a wife to Reggie.

Robin Phelps-Raymond is Founder and CEO of Red Admiral Ventures, a business acceleration company guiding women Founders/CEOs in scaling her leadership, team and business to 8-figures. Her personal vision is Transforming Lives, Livelihoods, and Communities through Entrepreneurship.

Robin spent the first half of her career working in sales and business development for technology start-ups in Silicon Valley. Her passion for and alignment with the PS27 Foundation vision and work of helping diverse Founders achieve sustainable growth is rooted in her experience on the same journey. In Aug of 1999 she co-founded with another female a software company in Orlando. With crucial support from the ecosystem in Central Florida for early-stage entrepreneurs and from Springboard Enterprises for women entrepreneurs, they raised a total of $13.1M of Angel and VC funding in 3 rounds with increasing valuation each round and were on a path to 8-figures. After closing the company in December of 2002 she embarked on her mission to change that outcome for women and other diverse Founders and help them succeed at building their business to 8-figures.

From 2012 – 2020 she was a Director of entrepreneurship programs at University of Central Florida, including NSF I-Corps, the UCF VentureLab, MegaWatt Ventures Cleantech business competition, and GrowFL statewide program for second-stage companies. Prior, she was a Director in Denver, CO for the non-profit CTEK, an organization supporting entrepreneurs with programs, business incubators, and CTEK Angels investor group.

Robin has her Bachelor of Science in Computer Science from Pepperdine University, her Master of Science in Management from University of Denver, and her PhD (ABD) from University of Colorado Denver. She lives in Sanford, Florida with her husband, John.

Randall Thomas is a staffing and talent acquisition thought leader who began his recruiting career at Modis, a company founded and headquartered here in Jacksonville, Florida. Since leaving Modis in 2022, Randall has consulted with companies from startups to Fortune 500 organizations to place top talent within their organizations. Recruiting expertise includes, but not limited to IT, Supply Chain, Legal, and Engineering roles.

Randall co-founded and is on the Board of Directors for Spivvel – a recruiting application aimed at providing pay transparency to candidates and eliminating screening bias in the recruitment process. Spivvel was recently accepted into Nvidia’s accelerator program, which provided Spivvel with a significant grant toward AI integration and cloud services.

In Spring of 2025, Randall will be publishing his first book, “Intakes to Start Dates” through Performance Publishing Group. Intakes to Start Dates is a modern view on the staffing business, providing details on full lifecycle recruiting and how technology is changing the talent industry.

Randall hosts a podcast titled PB & Jax, in which he meets with Pioneers and Builders in the city of Jacksonville to tell their stories, highlight their business, and discuss what things Jacksonville does well, as well as how the city can improve. PB & Jax recently partnered with the City of Jacksonville’s Small and Emerging Business division to be their exclusive podcast partner.

As a veteran himself, Randall is passionate in championing initiatives tailored toward veterans and mental health. Randall was featured in G.I. Jobs Magazine as a veteran excelling in their field in Corporate America.

Born and raised in Austin, Texas and spending 18 years here in Jacksonville, Randall is eager to take part in seeing the River City reach its full potential.