Program Manager Research Operations Jobs in Chicago, IL

The Technical Program Manager (TPM) will lead Cayuse's most consequential cross-functional initiative: migrating 500+ product instances across a 600+ customer base to a standardized, scalable platform. This role sits at the intersection of R&D, Product Management, and Professional Services, translating complex technical dependencies into clear execution plans and building a repeatable migration framework that serves as a durable operational asset for the company.

The TPM will be the single accountable owner of migration program strategy, delivery, and cross-functional alignment — partnering with engineering and product leadership to define the migration path and working hand-in-hand with Services to ensure every customer migration is executed with precision and minimal disruption.

• Own the end-to-end migration program: sequencing, milestones, cohort planning, risk management, and success criteria across all customer segments and product lines.
• Build and maintain a detailed project plan to migrate customers based on a prioritization framework that incorporates key criteria of the customer base.
• Build a standardized, repeatable migration framework that reduces per-customer effort over successive cohorts and scales with Cayuse's growth.
• Define and maintain the migration runbook, including tooling requirements, data validation standards, cutover procedures, rollback protocols, and customer communication templates.
• Track program health through clear metrics and surface tradeoffs to senior leadership before they become critical.
• Serve as the primary point of accountability for migration delivery timelines and outcomes.
• Champion the adoption of AI-powered tools across the team, providing hands-on guidance to accelerate workflows and improve migration outcomes.

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.

• 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.

• 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

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