RedSail Technologies: Who We Are

For more than 20+ years, Kraig has delivered outstanding growth for customers, shareholders, and employees in the healthcare technology market. He has a passion for helping customers provide world class healthcare in their communities through innovative technology and services.

In 2017, Kraig co-founded TrellisRx^®. TrellisRx partners with health systems to deliver life-changing outcomes to patients requiring specialty medication therapy. Kraig is currently the Executive Chair of the board for TrellisRx.

Previously, Kraig was CEO of Aesynt, Inc., the market leader for integrated pharmacy medication management solutions serving health systems globally. Under Kraig’s leadership, Aesynt^® returned to double-digit growth, tripled profits, returned to industry leading Net Promotor Score levels of customer loyalty and successfully exited the business to Omnicell, Inc. in 2016.

Kraig also served as CEO of Connecture^®, Inc. Connecture is a market leader in online health plan enrollment software, serving both commercial and Medicare insurance plans.

Prior to his appointment with Aesynt/McKesson Automation, Kraig was the president and CEO of CardiacAssist, Inc., an entrepreneurial therapeutic company that designs, manufactures, and markets a novel temporary heart assist technology.

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Jeff is the president of PioneerRx, RedSail Technologies’ premiere independent pharmacy software system. With a background in software development, he built PioneerRx from the code up. Over the past 14 years, Jeff’s leadership has made PioneerRx the most installed independent pharmacy management system in the country.

In addition to his role as president, Jeff also serves on the NCPA^® Innovation Board and is a host of the Catalyst Pharmacy Podcast, a production of PioneerRx. He is a Microsoft Certified Solutions Developer and an accomplished speaker.

Prior to creating PioneerRx, Jeff worked for Praeses^® where he developed and patented software called Jurisdiction Online that connects state governments with insurance companies for compliance with inspection requirements. He also taught computer science at LSU Shreveport. Many of his best students were his first employees at PioneerRx.

Jeff began his career at Factory Mutual Engineering (FME), analyzing business processing and identifying critical pathways to ensure businesses continue to operate in the event of equipment or system failure. He then received his Master of Science in Computer Systems Technology from LSU Shreveport and developed software for FME’s 1,000 plus global field engineers.

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Jerred Wilson is the Chief Technology Officer for RedSail Technologies’ Pharmacy Management Systems business unit. Leading the technology department, he oversees product and shared service engineering teams. With an undergraduate degree in Computer Science from Cameron University and MBA courses from The University of Iowa, Jerred’s marketing and business backgrounds inform his approach to technology products and prioritize users and business outcomes within the Software Development lifecycle.

He has held various roles throughout his career, from software engineering to leading IT departments, new product development, and product design. His achievements align with creating new technology-based businesses and increasing revenue from existing software products.

He is motivated by building effective, professional relationships and helping others grow and succeed. Jerred guides RedSail's technology architecture and delivery processes to maintain a market-leading position, leveraging his understanding of the product portfolio and markets served.

He uses a user-centered design approach to understand marketing and user mental models, resulting in increased adoption and financial success.

When he's not working, Jerred enjoys spending time outdoors with his family, namely mountain biking, fishing, and hiking. He and his wife Teri, have four children: Blake, Brooke, Bailey, and Braylon. He is also an avid fisherman who is actively involved in his church. He is an identical twin and recently relocated back to the U.S. after living in Portugal for a year.

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Bob joined RedSail Technologies in April 2020. He has 29 years of experience leading software/technology organizations and has spent a significant amount of time in the healthcare sector as well. Previous leadership positions include president, CIO, CTO, COO, and board member, and he’s worked for the following companies: Molina^®, Affiliated Computer Services/XEROX^™, Aetna^®, Connecture, BenefitFocus^®, and AT&T^®.

Bob holds an MBA from Nova University and a Bachelor of Engineering in Electrical Engineering from the University of Florida. He also holds multiple technology patents.

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As RedSail Technologies’ SVP and GM of Pharmacy Management Systems, Josh oversees the Pharmacy Management Systems business unit, leading Product, Sales, Marketing, and Implementations.

With an in-depth understanding of the healthcare ecosystem based on his extensive background, Josh holds a Doctor of Pharmacy (PharmD) degree from the University of Texas at Austin, an MBA with a concentration in Healthcare Administration and Quality/Process Improvement from the University of Texas at Dallas, and a Chief Product Officer Executive Certificate from Northwestern University.

His time at CVS/Health on the PBM side and as a dispensing pharmacist at Walgreens offered invaluable insights into pharmacy needs and industry challenges, informing his approach to product development and providing valuable perspective on supporting independent pharmacies.  

His knack for innovative problem-solving and deep user understanding has driven significant advancements in his career. He has served as Director of Integrated Care Pharmacy at DaVita Rx and launched over 2,000 new PioneerRx features, significantly enhancing user experience and operational efficiency.  

Outside work, Josh enjoys spending time with his family, including his wife Jessica, their daughter Ellis, and their two rescue dogs, Stella and Moose. An avid Gran Turismo player, bourbon collector, and craft cocktail enthusiast, he stays active with exercise, enjoys live music, and holds a third-degree black belt in taekwondo. His commitment to personal growth and family mirrors the dedication he brings to RedSail, where he is focused on nurturing future leaders and creating customer experiences for pharmacies and patients.

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Anthony joined RedSail Technologies in April 2020, bringing 30 years of healthcare technology leadership experience to our product management and marketing efforts. His career has always been about converting customer, technology, and market insights into targeted strategies and ultimately prioritizing portfolio solutions that ensure long-term growth and profitability. Though anchored in portfolio management, his roles have also included leading both development and commercial resources with a focus on GM-oriented responsibilities. He is currently leading our Network Services business unit, focused on delivering clinical and operational programs to our member facilities by leveraging our reach and uniquely integrated technology platform.

Most recently, Anthony held leadership positions within the pharmacy technology sector: SVP, Strategy/Portfolio and GM, Kirby Lester Retail Pharmacy at Capsa Healthcare; and SVP, Portfolio Realization for Aesynt, Inc., leading the Development, Product Management, and Marketing teams. Additional healthcare leadership roles included vice president, Informatics Business within Bayer HealthCare; SVP, Strategy and Solutions for TeleTracking^®; and various leadership positions during his tenure with MEDRAD^®, Inc., including leading Sales and Marketing as well as a Multi-Vendor Service organization. Prior to MEDRAD, Anthony spent 10 years with GE Industrial Systems focusing on automation principles.

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With 20 years of experience across diverse work environments, Drew has a proven track record of building growth businesses that deliver shareholder value through loyal customers, operational excellence, and financial performance.

Prior to joining the leadership team at RedSail Technologies, Drew served as chief financial officer at Capsa Healthcare, a market leader in reliable, cutting-edge mobile workstation and medication delivery solutions. In addition to his executive role, his functional responsibilities included accounting, finance, treasury, information services, and human resources.

Prior to Capsa Healthcare, Drew was the vice president of Finance at Omnicell^™, which delivers compelling automation so pharmacies can focus more on patient care. As part of the leadership transition team, he supported the execution of Omnicell’s integration plan that predominately centered around a synergistic consolidation while broadening their portfolio with centralized pharmacy robotics.

Prior to Omnicell, Drew was the vice president of Finance at Aesynt, Inc., a market leader for integrated medication management solutions serving health systems globally. He was a part of the leadership team that led the successful divestiture of Aesynt^® from McKesson Corporation. In addition to Drew’s executive role, his functional responsibilities included accounting, FP&A, and tax and treasury.

Drew holds a Bachelor of Science degree in Accounting from Indiana University of Pennsylvania and holds a Six Sigma certification from his time at McKesson Corporation.

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As chief strategy officer, Frances is responsible for strategy, M&A, and overall business processes. Most recently, Frances served as chief strategy office for Connecture, Inc. – a market leader in online health plan enrollment software. She was responsible for strategy, portfolio planning, and M&A and successfully led the sale of the Commercial Plan business unit to BenefitFocus and the Medicare Plan business unit to Harris Computers.

Prior to joining Connecture, Frances was the senior vice president of corporate strategy for Aesynt, Inc., a leading hospital pharmacy automation company. She led the development of strategy, which saw the business return from declining revenues to double-digit growth. In addition, Frances led the transition following the company’s sale to Francisco Partners, led the acquisition and integration of Health Robotics, and managed the sale process, which ultimately saw the company join Omnicell^™ in 2016.

In between executive roles, Frances consults independently to mid-market healthcare technology companies on growth strategy development and execution, portfolio planning, market analysis, and M&A targeting and diligence.

Frances began her healthcare focus as part of McKesson’s Corporate Strategy and Business Development Group, where she worked with senior executives across both the distribution and technology businesses. She joined McKesson from Bain & Company, where she was a management consultant. Her experience at Bain included growth strategy, global reorganization, and new market entry. It also cut across a range of industries including retail, oil and gas, and telecom.

Frances started her career with CGI Federal, where she developed a strong foundation in technology, holding several positions of increasing responsibility in client management and system design, development, and implementation.

She graduated with a Bachelor of Arts degree in Government and International Studies from the University of Notre Dame and was a Forte Fellow and Dean’s Scholar at the University of North Carolina’s Kenan-Flagler Business School, where she earned a Master of Business Administration degree.

Frances continues to be active with Kenan-Flagler, where she serves as a Next Generation Advisory Board Member for the school and an Alumni Advisory Board Member for the Center for the Business of Health.

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Joe joined the J M Smith Corporation^® in 1996 as a hardware technician at QS/1^®, and in 1998, he was part of the creation of QS/1’s Network Solutions Group. In 2004, J M Smith acquired Integral Technical Services of Greenville, SC, and formed Integral Solutions Group (ISG) as a separate business unit where he was integration manager. As ISG grew, Joe held many key positions and became the divisional president in 2016. In 2018, he became vice president of Human Resources at QS/1.

With the transition to RedSail Technologies, in addition to continuing to lead Human Resources and Information Technology, Joe took on the leadership role for compliance and legal services. He leverages continuous staff-lead process improvements to provide world-class support to all the RedSail Technologies’ business units. When not at work, Joe enjoys spending time with his family, camping, hiking, and riding his motorcycle.

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