Director of System Implementations

Job Description This is a remote position. ABOUT ICAREMANAGER iCareManager is a HIPAA-compliant, SOC 2 Type II certified EHR and care management platform serving IDD, assisted living, and human services providers across 30+ states. We have been building technology that improves outcomes for individuals with disabilities since 2011 — and we are accelerating. As we expand our provider base and deepen our AI-powered product capabilities, we are looking for an experienced Director of System Implementations to lead the team that turns new clients into long-term success stories. ROLE SUMMARY The Director of System Implementations owns the full implementation lifecycle at iCareManager. You will lead a team of Implementation Specialists, drive operational excellence across all client onboardings, and serve as the connective tissue between our clients and our Product, Engineering, and Customer Success teams. This is a high-impact leadership role where your work directly shapes client outcomes, retention, and company growth. WHAT YOU'LL DO Lead and Develop the Team Manage, coach, and grow a team of Implementation Specialists focused on delivering exceptional client onboarding experiences Build a culture of accountability, empathy, and continuous improvement Set clear performance expectations and track metrics that reflect real client outcomes — not just activity Own Implementation Operations Oversee all active implementations, ensuring projects are delivered on time, on scope, and to quality standards Use tools like Asana and Jira to manage workloads, surface risks early, and keep stakeholders aligned Serve as the escalation point for complex technical and organizational challenges Review and approve project deliverables including configurations, training plans, and go-live readiness assessments Drive Client Success During Onboarding Build strong relationships with new clients from day one, setting clear expectations and maintaining trust throughout the process Gather structured client feedback and translate it into actionable improvements across both process and product Champion client engagement through training programs, webinars, and user community initiatives Improve How We Work Identify gaps and inefficiencies in the implementation process and lead initiatives to close them Stay current on DDA, IDD, ALF, and Medicaid billing regulatory requirements — including state-specific billing rules, EVV mandates, and Medicaid program variations across the states we serve — that affect client configurations Collaborate with Product and Engineering to surface implementation insights that inform the product roadmap Collaborate Across the Business Partner with Sales during the pre-sales process — including demos and trade shows — to set accurate expectations and accelerate close Work with Customer Success to ensure smooth handoffs post-go-live and reduce time-to-value for new clients Provide regular reporting to leadership on team performance, implementation health, and client satisfaction trends Requirements WHAT YOU BRING Experience 4+ years in a healthcare or human services technology environment, with direct involvement in software implementations or system deployments 4+ years leading teams, with demonstrated ability to develop talent and manage performance in a remote setting Hands-on experience with EHR, care management, or human services platforms strongly preferred Familiarity with IDD, ALF, or behavioral health provider workflows — and awareness of Medicaid billing requirements, state-level billing variations, and EVV compliance across multiple states — is a significant plus Skills Strong project management fundamentals — you have run complex, multi-stakeholder implementations and know how to keep things on track Excellent communicator — you can translate technical concepts for non-technical audiences and hold difficult conversations with clients when needed Analytical mindset — you look at patterns across projects and turn them into process improvements Comfortable working in a fast-moving, remote-first environment with a high degree of ownership Education Bachelor's degree in Business, Healthcare Administration, or a related field required PMP certification is a plus; Master's degree preferred WHY JOIN ICAREMANAGER Work at a company with 15+ years of focused expertise in IDD and human services technology — not a generalist EHR trying to serve everyone Join at an inflection point: we are expanding our AI capabilities, growing our provider base, and scaling the team Remote-first culture with a collaborative, mission-driven team Competitive salary with performance-based bonus opportunities Medical insurance, 401(k) retirement plan, and paid PTO Real opportunities for career growth as the company scales Benefits 401(k) Retirement Plan Medical Insurance Paid Vacation and PTO Performance-Based Bonus Opportunities Opportunities for Professional Development and Career Growth