The Team Behind the Transformation

​Bill Flanagan is the Co-Founder and CEO of CareWork. With more than 30 years of experience in software development and product architecture, Bill plays a vital role in both the development and long-term vision of the CareWork platform.

Prior to co-founding CareWork, Bill founded and served as President of a time and labor-management software solution that grew to serve long-term and post-acute care organizations. Bill recognized the unique labor challenges in long-term and senior care and developed one of the first fully managed Payroll-Based Journal (PBJ) solutions to help operators more easily address the mandatory CMS reporting requirements.

In 2020, Bill co-founded CareWork with Jackie Ramieri to expand on his passion for long-term care labor efficiencies and deliver a holistic operational experience through digital transformation, workflow automation, and business intelligence to the industry.

Ralph is a highly experienced senior technology executive. He has led technology operations and strategy and major product development initiatives for a national PEO as well as for leading companies in the chemical and energy industries. He was CIO and executive vice president of technology for OneChem, a software application provider to the chemical industry, and held various senior technology management positions for Norsk Hydro, a global oil, gas, and aluminum producer. Ralph began his career with Arthur Andersen as a senior technology consultant.

​Ralph received a bachelor’s degree in economics from the University of Florida and earned a Master of Business Administration from the University of South Florida.

​Maria is a seasoned sales leader with broad business experience across Sales, Marketing, and Operations.

 She started her career by spending over a decade with The Ford Motor Company and the Legal & Regulatory Group of Thomson Reuters, before pursuing her passion of working with early stage startups.

Over the past 10 years, Maria has been involved in helping health care organizations develop their sales strategy and go-to-market messaging for national product launches. Her focus is promoting technology that provides access to business analytics that drive workflow process improvement, revenue optimization and increased patient outcomes.

Maria holds a B.S. in Business Administration from The Ohio State University Fisher School of Business. She lives in Lake Forest, IL with her husband and 3 children and enjoys all things outdoors.

Gary has 25 years of experience investing in cloud-based software in the Southeast with 19 years as a general partner and seed-stage VC investor.

Starting with Council Capital’s debut fund in 2000, Gary was a General Partner for 3 funds at Council Capital focused on seed and early-stage cloud software serving health care. Gary’s referencable track record includes leading 38 investments at the seed stage in the Southeast, achieving impressive returns. Prior to Council Capital, Gary was Principal at Stonehenge Growth Equity for 4 years. There he made his first seed stage investment, SecureTax.com, which is Intuit’s Web TurboTax today.

Gary’s experience as a seed stage & early stage investor began in 2000. Gary’s track record includes > 2 dozen seed & early stage investments in Valor’s target region, including 14 in Atlanta. In 2014, Gary left Council Capital to focus on active seed-stage investing personally, and joined Valor first as an investor and operating partner before joining the general partnership.

Amber LaRue has 25 years of experience in operations and is a small business entrepreneur with a passion for streamlining processes, empowering teams, and fostering client success. With a background spanning executive support, real estate brokerage assistance, and business management, Amber brings a versatile skill set to every project.

Amber’s professional journey includes certifications like Asana Pro, which amplify her project management capabilities, as well as deep expertise in strategic planning, employee training, and operational efficiency. She has implemented productivity frameworks like EOS and Strategic Coach, enabling businesses to optimize workflows and achieve sustainable growth.​

Amber has a track record of building strong relationships with clients, team members, and stakeholders. She has consistently driven profitability and performance improvements, leading her teams to achieve remarkable success, such as being recognized as the most profitable division for 6 consecutive quarters.

​Based in Southeast Missouri, Amber is dedicated to helping businesses and teams thrive.

Ken Hall is a Partner at DeepWork Capital and supports the firm in sourcing and executing investments, fund operations, portfolio management, and more. 

Prior to DeepWork, Ken worked for IBM in New York City, where he held numerous roles for IBM in Corporate Development and Corporate Venture Capital and supported some of the company’s most innovative brands, including IBM Watson, IBM Blockchain, Watson Health, Hybrid Cloud, and IBM Automation. He gained additional venture capital investment experience as a former advisor to 1843 Capital and various family offices where he supported over a dozen early stage investments ranging from industrial products to autonomous vehicles and cryptocurrency banks. 

Since moving to Florida, Ken quickly became an impactful member of the venture community with his unique passion for helping startup companies. Ken is currently the Chairman of Startups for the Orlando Tech Community where he leads initiatives to help early-stage companies throughout Central Florida. He is a frequent guest speaker at Rollins College, Stetson University, and the University of Central Florida and is an advisor/mentor to numerous startup accelerator programs and organizations, including Endeavor Miami, Techstars Miami, leAD Lake Nona, and Plug & Play.

Kevin Wilhelm is a seasoned entrepreneur, investor, and digital marketing leader with a strong track record of scaling businesses through strategic growth and operational excellence. He is the founder and CEO of POD Marketing, a full-service digital agency established in 2014 that has grown to 140 full-time team members and serves thousands of clients across North America. Under Kevin’s leadership, POD Marketing has expanded into 4 specialized divisions, each focused on key industries such as healthcare and home services.

In addition to his business accomplishments, Kevin is an Amazon best-selling author of Click: Transform Your Business Through Digital Marketing (2019), a guide for companies looking to unlock their potential through digital strategy.

As a board member at CareWork, Kevin brings a passion for building businesses rooted in culture, clarity, and long-term vision. Outside of his professional life, Kevin is a devoted family man who enjoys spending his time with his wife and 3 children.

Jackie Ramieri is the Co-Founder of CareWork. Jackie has worked in complex IT environments as a Solution Architect and CIO for more than 15 years. Since 2017, Jackie has worked to help skilled nursing and senior living operators navigate IT, security, and compliance requirements, improve IT operations, and become more efficient through the use of technology.​​

Jackie co-founded CareWork in 2020 to give owners, operators, and community leadership teams a way to unify operations, automate workflows, and eliminate duplicate work without the need to hire in-house IT experts. With help from skilled nursing, assisted living, independent living, and CCRC clients, she designed CareWork with the LTPAC community in mind. Jackie remains focused on problem-solving in the LTPAC community.