VP, Chief of Solution Strategy, Deputy CIO

eSimplicity•Columbia, MD

1d•$190,000 - $280,000•Remote

About The Position

eSimplicity is seeking a senior leader to serve as the strategic and operational extension of the CIO, driving solution strategy across all business units. This role will own the solution strategy discipline enterprise-wide, understanding technology integration within mission domains, shaping strategic direction, and leading initiatives to position eSimplicity for mission-critical wins. The position combines serving as the CIO's deputy, absorbing operational weight, and representing the CIO in cross-functional discussions, with leading solution strategy across all business units. The ideal candidate will lead and develop staff, own the day-to-day rhythm of the technology organization, and drive strategic vision grounded in deep domain understanding. This role requires strategic thinking, operational leadership, compelling communication skills, and a passion for building teams and enabling their success.

Requirements

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 participate meaningfully 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.

Nice To Haves

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.

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.