Eligibility / Qualification Required:
Cross-Functional Leadership- Drive alignment across R&D, Product Management, and Professional Services without direct organizational authority.
- Partner with engineering to lead the end-to-end design, development, testing, and execution of migration plans, ensuring alignment across teams and on-time delivery.
- Collaborate with Infrastructure to develop comprehensive runbooks, test strategies, and automation pipelines that streamline new instance provisioning, product migrations, and legacy instance decommissioning.
- Lead regular cross-functional working sessions to surface dependencies, resolve blockers, and maintain delivery momentum.
- Partner with Product to ensure the migration path is informed by roadmap priorities and technically sound.
- Partner with Professional Services to ensure the migration framework is operationally executable at scale.
- Represent the migration program in executive and board-level reporting as required.
Customer Experience & Delivery Quality- Coordinate with Customer Success to manage customer sequencing, readiness, and communication throughout migration windows.
- Define quality and acceptance criteria for each migration cohort; establish go/no-go gates and validation checkpoints.
- Minimize customer disruption by building robust pre-migration validation, rollback procedures, and post-migration support protocols.
- Identify and document lessons learned after each cohort to continuously improve the migration playbook.
- Drive continuous improvement of migration processes and tooling to reduce downtime, increase reliability, and shorten overall migration cycles.
Reporting & Operational Visibility- Build and maintain dashboards tracking migration velocity, cohort progress, risk status, and customer outcomes.
- Produce recurring reporting for R&D, Product, Services, and executive leadership.
- Deliver ad hoc analysis to identify emerging risks, capacity constraints, and opportunities to accelerate the program.
Qualifications
- 7+ years in Technical Program Management, Engineering Program Management, or a closely related role at SaaS companies.
- Demonstrated experience leading large-scale, multi-customer migration or platform transition programs from design through delivery.
- Proven ability to drive alignment across R&D, Product, and Go-to-Market organizations without direct reporting authority.
- Experience building structured program management frameworks, playbooks, and runbooks that outlive the program that created them.
- Exceptional written and verbal communication skills, including executive-level reporting and presentation.
- Strong analytical and problem-solving skills; comfortable with ambiguity and able to impose structure in fast-moving environments.
Nice to Have- Experience in research administration, higher education, or healthcare software markets.
- Technical fluency — able to engage substantively with engineers on data models, APIs, integration dependencies, and system architecture.
- Background in or exposure to managed services or professional services delivery models.
- Familiarity with SaaS customer lifecycle management (onboarding, adoption, renewal).
- PMP, PgMP, or equivalent program management certification.
How You’ll Be Measured- Migration velocity: customers moved to the new platform on schedule, within defined quality thresholds.
- Repeatability: measurable reduction in per-customer effort across successive migration cohorts.
- Cross-functional alignment: stakeholder confidence in program visibility, predictability, and communication.
- Customer experience: minimal disruption to customer operations during migration windows, measured by support volume and CSAT.
Benefits
- Competitive Medical Benefits (PPO + HSA available)
- Vision, Dental, Short-Term Disability fully covered by Cayuse
- Unlimited PTO + Holidays + Flexible Work Schedule
- Remote Work Stipend
- Equal Paid Parental Leave
- 401k with Employer Matching
- Quarterly Wellness Reimbursement
- Remote Work Environment, supporting the Ultimate Employee Experience
_Cayuse does not accept agency resumes. Please do not forward resumes to our jobs alias or any Cayuse employees. Cayuse is not responsible for any fees related to unsolicited resumes._Our culture is one of inclusion and belonging where everyone feels respected, treated justly, supported and nourished. We all share responsibility for creating and sustaining a work environment where differences are celebrated and we are empowered to strive for excellence. We’re proud to be an equal opportunity employer and actively seek to recruit, develop, and retain a diverse and talented workforce.
Benefits
Health Insurance
Vision, Dental, Short-Term Disability fully covered by Cayuse
Home Office Stipend
Remote Work Stipend
Wellness reimbursement
Quarterly Wellness Reimbursement
Paid Parental Leave
Equal Paid Parental Leave
Paid Time Off
Unlimited PTO + Holidays + Flexible Work Schedule
Remote-Friendly
Remote Work Environment, supporting the Ultimate Employee Experience
How to Apply:
Apply through the official Startup Jobs application flow.
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