Our Team - Optima

Our Team

Passionate, energetic industry pros

Optima is led by an energetic team of industry veterans who are passionate about software and healthcare.

Josh Pickus

Chief Executive Officer

Josh Pickus is responsible for Optima’s overall strategy and operations. Josh has more than twenty years of entrepreneurial experience in the technology industry. Prior to joining Optima, Josh served as CEO-in-Residence at Alpine Investors, as Chief Executive Officer of high-growth software companies Niku and Support.com, and as a member of the Board of Directors of DemandTec, Conversica and Meta Software. Josh is passionately committed to delivering products that enable Optima’s customers to improve healthcare for the elderly.

Dinesh Senanayake

Chief Financial Officer

Dinesh Senanayake manages Optima’s financial, administrative and strategic planning organizations. Dinesh has more than 15 years of experience as a financial leader in software and IT consulting, serving as chief financial officer for leading companies, including BIAS Corporation (an Oracle platinum partner), IBM’s Bermuda and Grand Cayman Agency, and Igility Limited Bermuda. His expertise in corporate financial strategy, budgeting and operations will support Optima’s continued revenue growth and leadership in the post-acute care industry.

Aaron Brandwein

Chief Revenue Officer

Aaron Brandwein directs the sales and marketing organizations. Aaron has more than twenty years experience in building revenue organizations for leading software companies focused on the healthcare industry. Prior to joining Optima, Aaron served as Executive Vice President of Sales and Marketing at Homecare Homebase, as Vice President of Sales and Marketing at HealthMEDX and as Vice President at HealthPort. Aaron believes passionately in empowering his team to exceed customer expectations.

Christine Jones

Chief Customer Officer

Christine is responsible for directing the support, professional services, training, clinical and customer success organizations. Christine has more than 20 years’ experience leading both development and services organizations for numerous technology companies including MemberSuite, Innovolt and Siemens. Prior to joining Optima, Christine served as Chief Operating Officer at MemberSuite, where she drove a cross-departmental, customer-centric focus throughout the organization. She is passionate about applying her diverse experience to build on our 25-year foundation of helping customers achieve success.

Jeff Browning

Chief Product & Engineering Officer

Jeff oversees the product and engineering organizations. He has more than 25 years’ experience running product and engineering organizations at technology leaders including IBM, Silverpop and SecureWorks. Before joining Optima, Jeff led development for IBM’s Marketing Cloud. He is committed to advancing Optima’s product delivery processes and driving continuing innovation for our customers.

Jason James

Chief Information Officer

Jason James leads the development and transformation of all IT applications, infrastructure, support and operations. James has over twenty years of experience modernizing IT organizations to ensure the highest level of performance. Prior to joining Optima, he directed IT for several fast-growth technology companies including EarthLink and PRGX. James is devoted to keeping clinicians connected to the technology they rely on at the point-of-care, so they can stay connected to their patients.

Bindu Crandall

Vice President of Marketing

Bindu Crandall leads the Company’s marketing organization. Bindu has more than twenty years of experience creating and implementing ROI-based marketing strategies. Prior to joining Optima, she held senior-level marketing and product management positions at various technology companies including Internap, McKesson and Scientific-Atlanta (now part of Cisco). Bindu is passionate about delivering on the Company’s commitment to improve the experience of aging.

Carol Lewis

Vice President of Human Resources

Carol Lewis is responsible for overseeing strategy and operations for Optima’s Human Resources and Talent programs. She brings 20 years of experience helping global technology companies build, scale and operationalize talent strategies that deliver a competitive advantage. Prior to Optima, she was a business unit HR leader for IBM Watson Customer Engagement, where she spearheaded workforce and development programs to drive business growth. Carol believes that attracting and retaining top talent is done best when organizations keep their people front and center. At Optima, that means building on our culture of “PINK” employees who are engaged, have opportunities for growth and are empowered to drive innovation and customer success.

Josh Phillips

Vice President of Engineering

Josh Phillips oversees the engineering and quality assurance organizations. With more than fifteen years of experience working in software development and engineering, he is skilled at managing high performance teams. Josh is committed to building innovative products that empower post-acute care providers to focus on improving the patient and provider experience.

Jonathan Skypek

Vice President of Product - Home Care

Jonathan Skypek is responsible for the design, development and delivery of the Optima’s Home Health and Hospice solutions. Jonathan brings more than 10 years of experience overseeing product and development for numerous SaaS-based technology companies. Prior to joining Optima, he led the home health and hospice product management team for Brightree, where he drove product strategy and operational excellence in support of evolving regulatory, clinical, revenue growth, point of care and interoperability requirements. He is passionate about delivering innovative products and services that delight customers and exceed expectations.

Tom Trice

Vice President of Therapy Solutions

Tom Trice oversees the development and delivery of therapy software for skilled nursing facilities, assisted living facilities and contract therapy companies. Tom has more than twenty years of experience in the long-term care industry. He has been with Optima for over ten years, and has led development efforts for every aspect of the patient lifecycle including case management, point-of-care, interoperability and revenue cycle management. Prior to joining Optima, he worked in billing and finance for Genesis Healthcare. He focuses on creating beautiful software that empowers therapists to be fully present with patients.


Steve Mackie

Steve Mackie

Founder, Chairman of Outcomemeasures.org

Steve Mackie serves as the Chairman of OutcomeMeasures.org, a nonprofit organization focused on the measurement of healthcare outcomes and the distribution, study and use of such data to improve human health and quality of life. He believes passionately in the potential for nationally benchmarked outcomes data to improve patient care and provider operations. Steve founded Optima in 1992 and served as its Chief Executive Officer until 2015.
Michael Katri

Michael Katri

Founder, Sr. Product Strategist

Michael Katri is responsible for creating and evangelizing the Company’s product vision. Michael joined Optima in 1998 and has overseen its product portfolio for over fifteen years. Michael is responsible for many of Optima’s innovative solutions, and is leading the Company’s expansion into homecare, outpatient clinics, business intelligence and e-signature.
Ryan Katri

Ryan Katri

Founder, Sr. Solutions Architect

Ryan Katri oversees Optima’s technology platform and product architecture. He joined the Company in 1993 and has served as the principal driver of its technology ever since. Ryan developed much of Optima’s core intellectual property and is committed to the continued evolution of its technology platform and product architecture.
Randy Wallin

Randy Wallin

Chief Security Officer, Head of Optima University

Randy Wallin is responsible for the security of Optima’s operations. His broad expertise has led him to wear many hats since he co-founded Optima over twenty years ago, and he now also directs Optima University, the Company’s internal training organization.