Chief Technology Officer, Health

Chief Technology Officer

eSimplicity is a modern digital services company that partners with government agencies to improve the lives and protect the well-being of all Americans, from veterans and service members to children, families, and seniors. Our engineers, designers, and strategists cut through complexity to create intuitive products and services that equip federal agencies with solutions to courageously transform today for a better tomorrow.

eSimplicity is seeking a transformational executive to lead strategic customer engagement, technology innovation, business growth, and delivery excellence across its federal portfolio, with an initial emphasis on the Healthcare market. This executive will partner closely with the President, COO, Growth, and Delivery leaders to shape customer strategy, expand market presence, improve operational performance, and build long-term customer relationships. The role is intentionally broad and provides the opportunity to assume expanded business unit leadership as the organization evolves.

Within our Health business, we support mission-critical programs across Medicare, Medicaid, and the broader healthcare ecosystem — from healthcare quality measurement, data quality analysis, and data analytics to fraud, waste, and abuse (FWA) detection — helping federal and state health agencies modernize how they deliver care, protect program integrity, and drive better outcomes for the beneficiaries who depend on them. As Chief Technology Officer, you will define and lead the technical vision that powers this work, building enterprise-scale solutions that translate deep domain expertise into secure, innovative technology that makes a measurable difference in beneficiaries' lives.

This role follows a hybrid schedule. Employees are required to work on-site Tuesdays and Thursdays, with remote work on other days as business needs allow.

Key Responsibilities :

• Develop and execute the strategic technical vision for our Health business.
• Coordinate closely with the CIO organization on best practices, guidelines, and standards, conduction technology reviews, and plan technical engagement opportunities.
• Build trusted executive relationships with government customers, industry partners, and key stakeholders.
• Provide executive leadership for delivery excellence, operational performance, customer satisfaction, and financial results.
• Partner with the Growth organization to shape opportunities, influence capture strategies, and support proposal development and oral presentations.
• Provide technical oversight to program delivery strategies, roadmap, and/or architecture for enterprise programs (Big Data/AI), and support execution of technology strategies and best practices (DevSecOps, DataOps, AnalyticOps, Cloud/SaaS, etc.) across customer programs and agencies
• Lead a team of Chief Solutions Architects and Strategists on technology strategy including cloud modernization, AI, DevSecOps, analytics, data, and digital transformation initiatives.
• Identify emerging technologies and mission needs to create differentiated customer solutions.
• Be part of the corporate development leadership team to assess M&A opportunities to bring new capabilities and growth.
• Coach and develop senior leaders while fostering accountability, collaboration, and high performance.
• Lead and support operating rhythms including portfolio reviews, technology roadmap, forecasting, and staffing reviews.
• Identify risks early, develop mitigation strategies, and communicate recommendations to executive leadership.
• Represent eSimplicity at customer meetings, industry events, and partner engagements.
• Develop and maintain strategic technology partnerships (e.g., AWS, Databricks).

Business Leadership & Delivery :

• Partner with Business Unit and Growth leaders to drive operational excellence across strategic federal portfolios.
• Support executive oversight of complex federal delivery programs.
• Collaborate with BU GM to monitor portfolio health, customer satisfaction, financial performance, staffing, and execution risks.
• Develop and maintain executive relationships with government customers.
• Collaborate with Growth on pipeline, capture, and strategic pursuits.
• Mentor senior delivery program leaders and architects.
• Support strategic planning, forecasting, and business reviews.

Requirements

Required Qualifications :

• Bachelor's degree in Business, Engineering, Computer Science, Information Technology, or related discipline.
• 15+ years of progressive leadership experience supporting Federal Government customers.
• Demonstrated experience leading large technology modernization, systems integration, or digital transformation initiatives.
• Experience with business growth, customer engagement, delivery leadership, and financial accountability.
• Proven ability to build executive-level customer relationships across CMS or HHS agencies.
• Strong understanding of cloud technologies, DevSecOps, Agile delivery, data, AI, and emerging technologies.
• Excellent executive communication, negotiation, and leadership skills.

Preferred Qualifications :

• Master's degree in Business Administration or related technical discipline.
• Experience with healthcare interoperability standards such as FHIR, HL7, X12, or CMS interoperability mandates (e.g., CMS-0057-F, TEFCA)
• Experience leading high-growth organizations within the GovCon market.

Success Measures :

• Growth in revenue, backlog, and qualified pipeline.
• Strong customer satisfaction and executive relationships.
• Healthy delivery portfolio with proactive risk management.
• Improved employee engagement, leadership development, and retention.
• Successful execution of strategic growth and technology initiatives.

Why Join eSimplicity? :

This is an opportunity to influence the future direction of a growing federal technology company by leading strategic customer initiatives, driving innovation, developing exceptional leaders, and shaping the next generation of mission-focused solutions.

Working Environment: eSimplicity supports a hybrid work environment operating within the Eastern time zone so we can work with and respond to our government clients. Expected hours are 9:00 AM to 5:00 PM Eastern unless otherwise directed by manager.

Occasional travel for training and project meetings. It is estimated to be less than 5% per year.

Benefits: eSimplicity offers a comprehensive benefits package, including medical, dental, and vision coverage, 401(k) retirement benefits, paid time off, paid holidays, life and disability insurance, and additional wellness and employee support programs. Eligibility may vary based on employment status and applicable plan terms.

Reasonable Accommodation: eSimplicity is committed to providing reasonable accommodations to qualified individuals with disabilities during the application and hiring process. Applicants who need assistance or an accommodation should contact Human Resources.

Equal Employment Opportunity: eSimplicity is an Equal Opportunity Employer, including disability and protected veteran status. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran status, disability, or any other legally protected status.