Senior Director, Professional Services

Location Miami, FL (On-site preferred; hybrid eligible within the tri-county area) Who We Are At Paradigm, we're revolutionizing home care through innovative technology. As the fastest-growing tech company in this sector, we empower home care agencies with cutting-edge solutions in billing automation, growth education, authorization management, and beyond. We believe that by streamlining agency operations with third-party payers like the Department of Veterans Affairs and Medicaid, we ultimately enhance the quality of care for seniors, veterans, and underserved communities. We foster a dynamic and collaborative work environment where new ideas are welcome, and creativity thrives. Joining our team means becoming part of a supportive community that values continuous learning and excellence. We're on a mission to revolutionize home care and are looking for passionate individuals to help us make a lasting, positive impact. Position Snapshot The Senior Director, Professional Services leads the function responsible for how customers realize value from Careswitch, Paradigm's home care Agency Management System (AMS). This leader owns delivery across the full post-sale arc: implementation, data migration and technical services, training and enablement, and ongoing product adoption. The role is a key part of Paradigm's operating model, which establishes Professional Services as a distinct, scalable function that turns signed contracts into live, productive, and expanding agencies. The Senior Director shapes the strategy for the Professional Services team in partnership with the Senior Vice President, Operations. The Senior Director inherits an early-stage Careswitch implementation practice and is expected to define the methodology, tooling, team structure, and delivery standards. The leader is hands-on in early implementations and complex escalations while building the team and systems to step back over time, and partners closely with Sales, Customer Success, Support, Product, and Engineering. This position reports to the Senior Vice President, Operations. Core Responsibilities Professional Services StrategyShape the Professional Services strategy and operating model, in partnership with the Senior Vice President, Operations: how the function is organized, staffed, tooled, and measuredDefine the services catalog: what is delivered in the included onboarding tier, what is offered as premium services, and how delivery paths map to agency size, complexity, and legacy systemRecommend how premium services are packaged and positioned, working with Sales, Product, and Operations leadership; own how each package is scoped and delivered once definedEstablish delivery governance, including scoping standards, statements of work, change control, and quality assuranceSet the annual priorities and roadmap for the function and report progress against them to Operations leadershipCareswitch ImplementationOwn the end-to-end implementation experience for new Careswitch agencies, from contract execution through go-live and graduation to Customer SuccessBuild and codify a repeatable implementation methodology with tiered delivery paths (self-service, guided, white-glove), project templates, configuration standards, and go-live readiness criteriaDrive time-to-value down through automation, in-product onboarding, and standardized playbooks, while protecting quality and agency-specific configuration needs (EVV, payers, authorizations, state program rules)Serve as executive sponsor and escalation point for complex, strategic, or at-risk implementationsData Migration and Technical ServicesLead the data migration practice for agencies moving to Careswitch from legacy AMS platforms (e.g., WellSky, KanTime, AxisCare, and others), including extraction, mapping, transformation, validation, and cutoverDefine migration standards, data-quality gates, and reconciliation procedures so that clients, caregivers, schedules, authorizations, and billing history arrive complete and accurateOversee technical configuration services such as payer and clearinghouse setup, EVV aggregator connectivity, and integrations with adjacent systemsTraining and EnablementBuild the customer education function: role-based training curricula for agency owners, schedulers, billers, and caregivers, delivered through live sessions, a self-paced learning platform, and in-product guidanceDevelop and maintain a certification program and a help center / knowledge base that drive self-sufficiency and reduce support volumeOwn internal product enablement for customer-facing teams (Sales, Customer Success, Support) so every team represents the platform accurately and consistentlyCreate and maintain implementation collateral, including project plans, data migration guides, configuration documentation, and go-live checklistsProduct AdoptionDefine what healthy adoption looks like for a home care agency and instrument it: active users, core-workflow adoption (scheduling, EVV, billing), and feature depth at 30/60/90 days and beyondDesign adoption programs that move agencies from live to proficient to expanding, in partnership with Customer Success and MarketingEstablish structured feedback loops that translate implementation and adoption insights into Product roadmap priorities, with clear reporting on friction points and requested capabilitiesIdentify adoption risk early and intervene before it becomes retention riskTeam and Cross-Functional LeadershipRecruit, develop, and lead a team of Implementation Managers, Migration Specialists, Trainers, and Enablement Specialists, with clear performance expectations, career paths, and accountability structuresStay close to the work: lead early implementations personally, own complex escalations, and use that direct exposure to improve the playbookOwn the Sales-to-Services handoff: scope alignment, expectation setting, and implementation readiness before contract execution, in partnership with Sales and SolutionsOwn the Services-to-Customer Success graduation, including health criteria and a clean transfer of contextServe as a member of the Operations leadership team, representing the customer onboarding and adoption experience and contributing to Ops 2.0 execution across functionsHow Success Is MeasuredWithin the first year, establish baselines, targets, and reporting for the followingTime-to-value: median days from contract signature to first billed visit in Careswitch, by tierOn-time go-live: percentage of implementations that go live within the committed windowMigration quality: data migration accuracy and rework rate; percentage of migrations completed without go-live delayAdoption: percentage of active users and adoption of core workflows (scheduling, EVV, billing) at 30/60/90 days post go-liveEnablement: training completion and certification rates; help-center self-resolution ratePremium services delivery: on-scope, on-time delivery of premium packages; scope-creep and rework ratesCustomer experience: implementation CSAT / NPS and early-life churn (first 120 days)Other duties as assigned Experience And Skills Minimum 8 years of experience in professional services, implementation, or customer delivery at a SaaS company, with a track record of building or scaling a delivery functionMinimum 3 years of experience leading teamsExperience designing implementation methodologies and tiered delivery models (self-service, guided, white-glove) and operating them at scaleHands-on experience leading data migration and technical onboarding, including migrations from competing platformsExperience building customer education or enablement programs: curriculum design, learning platforms, certification, and help-center contentAbility to define product adoption measures and run programs that move customers from live to proficientDomain expertise in home care, home health, or adjacent healthcare operations, including scheduling, EVV, payer and Medicaid/VA billing, authorizations, and the day-to-day realities of agency staffFamiliarity with Agency Management Systems (e.g., WellSky, KanTime, AxisCare, AlayaCare) or comparable healthcare operations platformsStrong process orientation: designs scalable playbooks and standards while staying agile enough for a growing productCommunicates with credibility to frontline team members, cross-functional leaders, and agency ownersData-driven operator who defines metrics, builds reporting, and manages the team to itExperience leading through rapid growth, an acquisition, a product launch, or a significant platform expansionFamiliarity with change management frameworks (e.g., Prosci, ADKAR) and their application to customer onboardingPrior experience in a home care or healthcare SaaS company that also operated a managed-services line preferredExperience with customer-education tooling (LMS, in-product guidance) and project or PSA tooling preferred Education And Qualifications Bachelor's Degree in Business Administration, Healthcare Administration, Information Technology, or a related field, or an equivalent combination of education and relevant experience What We Offer Medical, dental, and vision benefits401k retirement planPaid time offProfessional development support Compensation Starting at $165,000 based on experience