Program Manager, CS Tools & Technology

Flex•New York, NY

15h•Hybrid

About The Position

Flex is rewriting the rules of rent payment, and our CS Tools & Technology team is at the center of making that experience seamless for every renter we serve. As a Technical Program Manager on the CS Tools & Technology team, you'll report directly to the Director of CS Tools & Technology and own the systems, programs, and integrations that power Flex's customer support operations — from Zendesk and automation pipelines to custom-built internal tools and cross-functional integrations. This is not a traditional TPM role. While you'll own program delivery, backlog prioritization, and roadmap execution, this role requires deep, hands-on involvement in designing, building, and operating solutions across our CS Tools & Technology stack. You'll operate as a builder-operator: someone equally comfortable presenting a strategic roadmap to senior leadership and then personally diving into Zendesk workflows, APIs, or automation logic to bring that roadmap to life. The ability to move fluidly between strategy, technical execution, and operational detail — without losing momentum in any layer — is what sets this role apart. Success here means you're the connective tissue between CS, Product, Engineering, Finance, and BPO partners — translating operational pain points into scalable technical solutions, keeping complex workstreams moving, and ensuring our CS Tools & Technology stack grows with the business. If you thrive at the intersection of strategy, execution, and technical craft, this role was built for you.

Requirements

4–7 years of experience in technical program management, business systems, or support technology with a track record of increasing ownership and end-to-end delivery
Proven builder-operator mindset: the ability to own program delivery while also executing hands-on within systems, integrations, and automation logic
Deep hands-on experience with Zendesk administration, including workflow design, routing logic, SLA management, and troubleshooting
Practical experience with APIs, webhooks, and automation tools (Zapier or equivalent) for system integration and workflow automation
Demonstrated use of AI-assisted development tools to build or guide custom solutions — this is an expectation of the role, not a nice-to-have
Strong written and verbal communication skills, including experience producing executive-facing materials such as roadmaps, status updates, and project briefs
Ability to operate independently across multiple concurrent workstreams in a fast-moving, high-growth environment
Experience collaborating cross-functionally with teams such as Product, Engineering, Finance, and external BPO partners

Nice To Haves

Experience in FinTech or high-growth consumer tech environments
Familiarity with BPO operations and multi-partner support models
Exposure to WFM tools (e.g., Tymeshift, Assembled), Salesforce, or similar platforms
SQL or data querying experience

Responsibilities

Own and manage the team's backlog, sprint planning, and prioritization across all active workstreams, driving end-to-end delivery of large-scale initiatives such as tool migrations, live chat, telephony, and internal tooling
Translate business needs and operational pain points into clear functional specifications, user stories, and acceptance criteria — then personally configure, integrate, or guide development of those solutions hands-on
Lead UAT planning to ensure solutions meet real-world operational needs before launch, and document systems, workflows, and integrations to support long-term scalability and knowledge transfer
Configure and administer CS platforms — primarily Zendesk — including triggers, automations, routing logic, SLA management, and agent workspace design
Design and implement integrations using APIs, webhooks, and automation tools such as Zapier, scoping technical feasibility and maintaining scalable pipelines
Own CS operational dashboards and reporting, partnering with CS leadership to define KPIs, surface insights, and drive data-informed decisions
Leverage AI-assisted development tools (e.g., Claude, GitHub Copilot) to build or guide custom solutions, and champion AI-enabled workflows across the team
Produce executive-ready outputs — roadmaps, status updates, project briefs, and post-implementation reviews — while identifying risks and unblocking dependencies across cross-functional teams