Technical Program Manager

Cypress HCM; United States; On-site; USD 107,000 - 118,000; Full time

Job summary

Cypress HCM is seeking a Contract Technical Program Manager to drive cross-functional execution across Cancellations, Reservations, and Services. You will collaborate with Engineering, Product, Design, and Data Science to keep features on schedule and dependencies unblocked across Web, iOS, and Android.

The role emphasizes translating complex technical work into clear leadership updates and contributing to product release planning in a high-scale consumer platform environment.

Qualifications

• 7+ years of Technical Program Management experience driving cross-functional software programs to completion.
• Experience with consumer-facing product surfaces such as reservations, cancellations, or service tooling is a plus.
• Ability to understand and reason about technical systems including frontend/backend integrations across Web, iOS, and Android.

Responsibilities

• Own program execution for Cancellations, Reservations, and Services initiatives; track milestones, surface risks, and drive resolution across Web, iOS, and Android engineering teams.
• Partner with Engineering Managers, Tech Leads, and PMs to align roadmaps, sequence work, and ensure cross-team dependencies are visible and unblocked.
• Drive the delivery of key workstreams including cancellation policy systems, reservation management flows, host/guest service tooling, and related trust and support infrastructure.
• Run regular program cadences (standups, cross-functional syncs, stakeholder updates) to keep progress visible.
• Identify and mitigate technical and execution risks before they become blockers.
• Contribute to bi-annual product release planning by managing workstreams through the product lifecycle.
• Translate complex technical work into clear status communications for engineering directors and senior leadership.

Skills

Technical Program Management

Cross-functional collaboration

Stakeholder management

Clear communication

Ambiguity management

Multi-platform delivery

Job description

• The Technology team is looking for a Contract Technical Program Manager (TPM) to drive execution across our Cancellations, Reservations, and Services programs. This is a high-impact, cross-functional role embedded within the engineering organization, supporting some of the most business-critical surfaces on the platform: the systems that manage how hosts and guests navigate bookings, changes, and service delivery.
• You’ll work directly with Engineering, Product, Design, and Data Science to ensure features ship on time, dependencies are managed proactively, and the team is moving with clarity and purpose.

Description

• The Technology team is looking for a Contract Technical Program Manager (TPM) to drive execution across our Cancellations, Reservations, and Services programs. This is a high-impact, cross-functional role embedded within the engineering organization, supporting some of the most business-critical surfaces on the platform: the systems that manage how hosts and guests navigate bookings, changes, and service delivery.
• You’ll work directly with Engineering, Product, Design, and Data Science to ensure features ship on time, dependencies are managed proactively, and the team is moving with clarity and purpose.

Duties

• Own program execution for Cancellations, Reservations, and Services initiatives. Track milestones, surface risks, and drive resolution across Web, iOS, and Android engineering teams
• Partner with Engineering Managers, Tech Leads, and PMs to align roadmaps, sequence work, and ensure cross-team dependencies are visible and unblocked
• Drive the delivery of key workstreams including cancellation policy systems, reservation management flows, host/guest service tooling, and related trust and support infrastructure
• Run regular program cadences (standups, cross-functional syncs, and stakeholder updates) to keep progress visible and
• Identify and mitigate technical and execution risks before they become blockers
• Contribute to bi-annual product release planning by managing Cancellations, Reservations, and Services workstreams through product lifecycle
• Translate complex technical work into clear status communications for engineering directors and senior leadership

Requirements

• 7+ years of Technical Program Management experience, with a track record of driving cross-functional software programs to completion
• Experience working on consumer-facing product surfaces. Reservations, cancellation flows, customer service tooling, or trust and safety systems are a strong plus
• Ability to understand and reason about technical systems, including frontend/backend integrations and multi-platform delivery (Web, iOS, Android)
• Strong stakeholder management skills. Able to lead through influence with no direct authority
• Comfort operating in ambiguity. You know how to make order out of chaos and keep programs moving
• Experience with a high-scale consumer platforms is a plus
• Excellent written and verbal communication. You can synthesize complex tradeoffs and present at the right altitude for any audience

Compensation

• $78.56 – 86.21/hr W—2