Technical Program Manager – Platform Migration

This is a fully remote position, open to applicants in United States.

📋 Description

• Take ownership of the complete migration program, including sequencing, milestones, cohort planning, risk management, and success criteria across all customer segments and product lines.

• Develop and uphold a comprehensive project plan for migrating customers, utilizing a prioritization framework that considers key criteria of the customer base.

• Create a standardized, repeatable migration framework that minimizes per-customer effort across successive cohorts and scales with Cayuse’s growth.

• Establish and maintain the migration runbook, detailing tooling requirements, data validation standards, cutover procedures, rollback protocols, and customer communication templates.

• Monitor program health through clear metrics and present trade-offs to senior leadership before they escalate into critical issues.

• Act as the primary accountability point for migration delivery timelines and outcomes.

• Advocate for the adoption of AI-driven tools within the team, offering hands-on guidance to enhance workflows and improve migration results.

• Foster alignment among R&D, Product Management, and Professional Services without direct organizational authority.

• Collaborate with engineering to manage the end-to-end design, development, testing, and execution of migration plans, ensuring team alignment and timely delivery.

• Work closely with Infrastructure to create comprehensive runbooks, testing strategies, and automation pipelines that facilitate new instance provisioning, product migrations, and legacy instance decommissioning.

• Lead regular cross-functional working sessions to identify dependencies, address blockers, and sustain delivery momentum.

• Collaborate with Product to ensure the migration path aligns with roadmap priorities and is technically sound.

• Partner with Professional Services to ensure the migration framework is operationally executable on a large scale.

• Represent the migration program in executive and board-level reporting as necessary.

• Coordinate with Customer Success to manage customer sequencing, readiness, and communication during migration phases.

• Define quality and acceptance criteria for each migration cohort, establishing go/no-go gates and validation checkpoints.

• Reduce customer disruption by implementing robust pre-migration validation, rollback procedures, and post-migration support protocols.

• Identify and document lessons learned after each cohort to enhance the migration playbook continuously.

• Promote ongoing improvements in migration processes and tools to decrease downtime, enhance reliability, and shorten overall migration cycles.

• Create and maintain dashboards that track migration velocity, cohort progress, risk status, and customer outcomes.

• Generate recurring reports for R&D, Product, Services, and executive leadership.

• Provide ad hoc analysis to pinpoint emerging risks, capacity constraints, and opportunities to expedite the program.

⛳️ Requirements

• Over 7 years of experience in Technical Program Management, Engineering Program Management, or a similar role in SaaS companies.

• Proven track record of leading large-scale, multi-customer migration or platform transition programs from design through to delivery.

• Demonstrated ability to drive alignment among R&D, Product, and Go-to-Market teams without direct reporting authority.

• Experience in developing structured program management frameworks, playbooks, and runbooks that endure beyond the program that created them.

• Outstanding written and verbal communication skills, including the ability to produce executive-level reports and presentations.

• Strong analytical and problem-solving abilities; adept at navigating ambiguity and imposing structure in dynamic environments.

🏝️ 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