Senior Director, Professional Services

Location

Miami, FL (On-site preferred; hybrid eligible within the tri-county area)

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 Strategy
  • Shape the Professional Services strategy and operating model, in partnership with the Senior Vice President, Operations: how the function is organized, staffed, tooled, and measured
  • Define 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 system
  • Recommend how premium services are packaged and positioned, working with Sales, Product, and Operations leadership; own how each package is scoped and delivered once defined
  • Establish delivery governance, including scoping standards, statements of work, change control, and quality assurance
  • Set the annual priorities and roadmap for the function and report progress against them to Operations leadership
• Careswitch Implementation
  • Own the end-to-end implementation experience for new Careswitch agencies, from contract execution through go-live and graduation to Customer Success
  • Build and codify a repeatable implementation methodology with tiered delivery paths (self-service, guided, white-glove), project templates, configuration standards, and go-live readiness criteria
  • Drive 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 implementations
• Data Migration and Technical Services
  • Lead 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 cutover
  • Define migration standards, data-quality gates, and reconciliation procedures so that clients, caregivers, schedules, authorizations, and billing history arrive complete and accurate
  • Oversee technical configuration services such as payer and clearinghouse setup, EVV aggregator connectivity, and integrations with adjacent systems
• Training and Enablement
  • Build 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 guidance
  • Develop and maintain a certification program and a help center / knowledge base that drive self-sufficiency and reduce support volume
  • Own internal product enablement for customer-facing teams (Sales, Customer Success, Support) so every team represents the platform accurately and consistently
  • Create and maintain implementation collateral, including project plans, data migration guides, configuration documentation, and go-live checklists
• Product Adoption
  • Define 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 beyond
  • Design adoption programs that move agencies from live to proficient to expanding, in partnership with Customer Success and Marketing
  • Establish structured feedback loops that translate implementation and adoption insights into Product roadmap priorities, with clear reporting on friction points and requested capabilities
  • Identify adoption risk early and intervene before it becomes retention risk
• Team and Cross-Functional Leadership
  • Recruit, develop, and lead a team of Implementation Managers, Migration Specialists, Trainers, and Enablement Specialists, with clear performance expectations, career paths, and accountability structures
  • Stay close to the work: lead early implementations personally, own complex escalations, and use that direct exposure to improve the playbook
  • Own the Sales-to-Services handoff: scope alignment, expectation setting, and implementation readiness before contract execution, in partnership with Sales and Solutions
  • Own the Services-to-Customer Success graduation, including health criteria and a clean transfer of context
  • Serve as a member of the Operations leadership team, representing the customer onboarding and adoption experience and contributing to Ops 2.0 execution across functions
• How Success Is Measured
  • Within the first year, establish baselines, targets, and reporting for the following
  • Time-to-value: median days from contract signature to first billed visit in Careswitch, by tier
  • On-time go-live: percentage of implementations that go live within the committed window
  • Migration quality: data migration accuracy and rework rate; percentage of migrations completed without go-live delay
  • Adoption: percentage of active users and adoption of core workflows (scheduling, EVV, billing) at 30/60/90 days post go-live
  • Enablement: training completion and certification rates; help-center self-resolution rate
  • Premium services delivery: on-scope, on-time delivery of premium packages; scope-creep and rework rates
  • Customer 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 function
• Minimum 3 years of experience leading teams
• Experience designing implementation methodologies and tiered delivery models (self-service, guided, white-glove) and operating them at scale
• Hands-on experience leading data migration and technical onboarding, including migrations from competing platforms
• Experience building customer education or enablement programs: curriculum design, learning platforms, certification, and help-center content
• Ability to define product adoption measures and run programs that move customers from live to proficient
• Domain 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 staff
• Familiarity with Agency Management Systems (e.g., WellSky, KanTime, AxisCare, AlayaCare) or comparable healthcare operations platforms
• Strong process orientation: designs scalable playbooks and standards while staying agile enough for a growing product
• Communicates with credibility to frontline team members, cross-functional leaders, and agency owners
• Data-driven operator who defines metrics, builds reporting, and manages the team to it
• Experience leading through rapid growth, an acquisition, a product launch, or a significant platform expansion
• Familiarity with change management frameworks (e.g., Prosci, ADKAR) and their application to customer onboarding
• Prior experience in a home care or healthcare SaaS company that also operated a managed-services line preferred
• Experience 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 benefits
• 401k retirement plan
• Paid time off
• Professional development support

Compensation

Starting at $165,000 based on experience