About Us 

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. 

Purpose and Scope 

eSimplicity is growing in scale, complexity, and mission impact. As we expand across health IT, defense, intelligence, and civilian programs, we need a senior leader who can serve as the strategic and operational extension of the CIO while driving solution strategy across all business units. The V.P. Chief of Solution Strategy, Deputy CIO will own the solution strategy discipline enterprise-wide: understanding how technology integrates within mission domains, shaping strategic direction in collaboration with the CIO and BD/Program teams, and independently leading strategy initiatives that position eSimplicity for mission-critical wins. This is a strategist, not an architect. The right candidate is someone who develops strategies for complex mission environments, whether that means data integration on the battlefield, claims analytics and policy development at CMS, or modernizing citizen-facing services across agencies. 

This role combines two critical functions. First, serving as the CIO's deputy: absorbing operational weight, representing the CIO in cross-functional discussions, and making judgment calls on priorities. Second, leading solution strategy across all business units. You will lead and develop the staff organization through a combination of direct reports and dotted-line collaboration, own the day-to-day rhythm of the technology organization, and drive the strategic vision, grounded in deep domain understanding, that shapes how eSimplicity competes and delivers. Some initiatives you will co-lead with the CIO and BD/Program teams; others you will own and drive independently. 

If you think strategically but lead operationally, can tell a compelling story about technical direction to engineers, executives, and agency stakeholders, and find purpose in building teams and clearing the path for them to deliver, this role was designed for you. 

Responsibilities 

• Serve as the CIO’s Deputy, representing the technology organization in leadership discussions, stakeholder engagements, and cross-functional decision-making with the authority to act on the CIO’s behalf. 
• Own and drive solution strategy across all business units by developing strategic technical approaches and innovation roadmaps, leveraging existing domain knowledge while actively building expertise in mission areas where gaps exist. Work both in collaboration with the CIO and BD/Program teams and independently as the strategy lead. Participate in solution development without owning the architectural design. 
• Lead and develop the staff organization across multiple teams through a combination of direct reports and dotted-line collaboration, conducting regular 1:1s, career development conversations, and performance management. 
• Translate the CIO’s technical direction and strategic vision into actionable plans, priorities, and execution roadmaps across the technology organization. 
• Drive people leadership at scale, including hiring, onboarding, mentoring, and retaining top talent while fostering a culture of accountability, curiosity, and continuous improvement. 
• Own process leadership across the technology organization, establishing and refining operational cadences, decision frameworks, and communication rhythms that keep teams aligned and unblocked. 
• Lead solution-oriented thinking across business units, ensuring teams deliver strategies and solutions that meet mission needs, drive competitive differentiation, and position eSimplicity for growth. 
• Serve as an active listener and trusted advisor across the organization by hearing team concerns, synthesizing ground-level feedback, and ensuring leadership decisions are informed by real context. 
• Communicate technical strategy, solution direction, and organizational priorities to diverse audiences, including engineers, executives, and government agency leadership, with clarity and compelling narrative. 
• Coordinate cross-program and cross-agency strategy initiatives, applying and growing domain knowledge across areas such as data integration in defense environments, claims analytics and policy development at CMS, and citizen services modernization to ensure consistent and informed solution approaches across all programs. 
• Identify operational risks, resource constraints, and organizational gaps before they become blockers, and drive resolution proactively. 
• Partner with BD/Growth and Capture teams to lead or co-lead solution strategy for new opportunities, shaping technical volumes and ensuring delivery readiness for awarded contracts. 
• Build and maintain organizational health metrics, tracking team engagement, delivery velocity, retention, and capacity to inform leadership decisions. 
• Perform other duties as assigned. 

Required Qualifications 

• Ability to obtain and maintain security clearances up to Secret/Top Secret. Must be a U.S. citizen. 
• A bachelor’s degree in Computer Science, Information Technology, Engineering, Business Administration, or a related field. (In lieu of a degree, an equivalent combination of education and experience will be considered). 
• Minimum of 12 years of progressive experience in technology leadership roles, with at least 5 years in a senior leadership capacity managing multiple teams through direct and dotted-line reporting structures. 
• Demonstrated ability to serve as a strategic proxy for executive leadership, making decisions, representing organizational priorities, and driving execution with minimal oversight. Experience leading solution strategy across multiple business units or program areas. 
• Broad technical acumen across software engineering, cloud infrastructure, data platforms, and modern delivery practices, sufficient to engage credibly with technical teams, understand how solutions integrate within mission domains, and participatemeaningfully in solution strategy without owning the architectural design. 
• Proven track record of people leadership: hiring, developing, and retaining high-performing technical teams in a fast-paced environment. 
• Exceptional storytelling and strategic communication skills, with the ability to translate complex technical concepts into compelling narratives for executive, government, and technical audiences. 
• Experience in federal government contracting, with an understanding of the GovCon operating model, contract vehicles, and agency engagement patterns. 
• Experience working within an Agile or SAFe (Scaled Agile Framework) environment. 
• Excellent verbal, written, and presentational communication skills. 

Desired Qualifications 

• Experience supporting CMS, Medicare/Medicaid, or other HHS programs. 
• Experience with DoD or Intelligence Community programs and associated security frameworks. 
• Experience in a Chief of Staff, Deputy CIO/CTO, VP of Engineering, Solution Strategist, or equivalent operational and strategy leadership role. 
• PMP, SAFe Agilist (SA), or similar program/portfolio management certifications. 
• Master’s degree in a relevant field (MBA, MS in Engineering/CS, or related). 
• Domain expertise in one or more of eSimplicity's core mission areas, such as defense data integration (e.g., CDAO, battlefield data systems), health IT analytics (e.g., CMS claims, policy development), or civilian services modernization. 
• Familiarity with modern AI/ML platforms, data engineering tools (Databricks, Snowflake), and cloud ecosystems (AWS, Azure). 
• Experience scaling operations in a high-growth digital services or professional services firm. 
• Track record of building cross-functional relationships across BD, delivery, and corporate functions. 

Working Environment 

eSimplicity supports a remote work environment operating within the Eastern time zone so we can work with and respond to our government clients. Candidates located in the Washington, D.C. / Maryland / Northern Virginia corridor are highly preferred. Expected hours are 9:00 AM to 5:00 PM Eastern unless otherwise directed by manager. 

Occasional travel for training, project meetings, and leadership engagements. It is estimated to be 10-15% 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.