Jobs · Management

Director, Enterprise Program Management

Swooped · United States · 4 days ago
RemoteRemoteManagement$220k–$250k/yrFull-time

About the role

The Managing Director is the accountable leader for the end-to-end success of a significant program for a strategic customer. Reporting directly to the CCO, this role owns the plan, the people, the customer relationship, and the outcomes from kickoff through go-live and into Phase II and beyond. This is a high-visibility, high-stakes assignment requiring a seasoned operator who can run a complex, multi-workstream program while simultaneously managing a strategic customer relationship.

Responsibilities

  • Serve as the single point of accountability from the POC to full deployment and beyond.
  • Drive and govern the master project plan across: Onboarding & Configuration, Training & Enablement, Data Migration, Integration, Rollout Execution, Support, and Reporting.
  • Chair weekly program stand-ups, steering committee sessions, and executive check-ins.
  • Own risk identification, escalation, and resolution.
  • Act as the primary executive-level contact for the strategic customer stakeholders throughout the engagement.
  • Build trust and alignment with project sponsors, operations leads, and office champions.
  • Navigate competing priorities, stakeholder ambiguity, and scope discussions with clarity and confidence.
  • Represent Karbon's capabilities, roadmap, and commitment with credibility at every level of the customer’s organization.
  • Lead and coordinate a cross-functional Karbon team including: Project Management, Implementation, CS, Training, and Support, with collaboration across Product and Engineering.
  • Ensure clear role ownership and handoffs across the multi-office implementation for the POC and all elements of Phase II.
  • Identify and resolve resource gaps as the program scales through the June–August high-volume rollout window for the POC and Phase II.
  • Deliver Go-Live for all offices by the target date, with users trained, data migrated, and integrations validated and converted to Phase II.
  • Maintain a live risk register and ensure confidence levels across nine identified program risks remain within acceptable thresholds.
  • Drive post-go-live health reporting through Fall 2026, producing the POC wrap-up deliverable for executive review.
  • Define what POC success looks like and position the engagement for conversion to a full commercial deployment.

Requirements

  • 10+ years of experience leading complex enterprise SaaS implementations or customer success programs, with P&L or program-level accountability.
  • Demonstrated success managing multi-workstream deployments with 100+ end-user locations, tight deadlines, and senior customer stakeholders.
  • Strong command of project governance: risk management, dependency tracking, milestone reporting, and executive communication.
  • Experience directly leading and managing cross-functional teams, with full people management authority over implementation, CS, training, and support functions.
  • Track record of navigating ambiguous, high-stakes situations and making sound decisions under pressure.
  • Exceptional communication skills - equally effective in a steering committee with a strategic customer and an internal team stand-up.
  • Background in practice management, accounting, or professional services technology.
  • Familiarity with Karbon or comparable workflow/work management platforms.
  • Experience with enterprise rollouts involving custom integrations and multi-tenant architectures.
  • Prior experience with large franchise networks or tax/accounting industry clients.

Qualifications

  • Experience with enterprise rollouts involving custom integrations and multi-tenant architectures.
  • Prior experience with large franchise networks or tax/accounting industry clients.

Skills

  • Project Governance
  • Risk Management
  • Dependency Tracking
  • Milestone Reporting
  • Executive Communication
  • Customer Success Programs
  • Enterprise SaaS Implementations
  • Complex Program Management
  • Team Leadership
  • Stakeholder Management
  • Communication Skills
  • High-Stakes Decision Making
  • Dealing with Ambiguity
  • Collaboration
  • Multi-Office Implementation
  • Resource Management
  • Go-Live Delivery
  • Post-Go-Live Health Reporting
  • Program Risk Management
  • Customer Relationship Management
  • Customer Engagement
  • Customer Success
  • Customer Satisfaction
  • Customer Retention
  • Customer Service
  • Customer Support
  • Customer Experience
  • Customer Journey Mapping
  • Customer Feedback
  • Customer Journey Optimization
  • Customer Journey Design
  • Customer Journey Analysis
  • Customer Journey Analytics
  • Customer Journey Insights
  • Customer Journey Strategy
  • Customer Journey Planning
  • Customer Journey Execution
  • Customer Journey Monitoring
  • Customer Journey Evaluation
  • Customer Journey Improvement
  • Customer Journey Innovation
  • Customer Journey Transformation
  • Customer Journey Evolution
  • Customer Journey Evolutionary Thinking
  • Customer Journey Evolutionary Strategy
  • Customer Journey Evolutionary Planning
  • Customer Journey Evolutionary Execution
  • Customer Journey Evolutionary Monitoring
  • Customer Journey Evolutionary Evaluation
  • Customer Journey Evolutionary Improvement
  • Customer Journey Evolutionary Innovation
  • Customer Journey Evolutionary Transformation
  • Customer Journey Evolutionary Evolution
  • Customer Journey Evolutionary Development
  • Customer Journey Evolutionary Growth
  • Customer Journey Evolutionary Expansion
  • Customer Journey Evolutionary Expansionism
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