Technical Program Director

Cast & Crew•Remote - United States of America, CA

4d•$170,000 - $185,000

About The Position

This role will lead the technical implementation of complex strategic initiatives that cross multiple product, engineering, and data teams. Key initiatives of focus will be Slate and possibly Payroll Services Automation and TTC Stabilization. Cast & Crew runs a portfolio of high-priority, multi-faceted engineering initiatives that cut across product, engineering, infrastructure, and business operations teams — the kind of programs where a missed dependency or a late escalation can ripple into a missed deliverable. The Technical Program Director (TPD) is accountable for the delivery rigor of these programs: keeping scope, timeline, and budget under control; keeping information flowing across contributing teams and up to executive stakeholders; and surfacing and resolving risks before they threaten the delivery schedule. This is explicitly not a product management role. The TPD does not own product vision, roadmap prioritization, or feature requirements. Instead, the TPD partners with Product, Engineering leadership, and workstream owners to instill the program discipline — planning, sequencing, dependency management, and escalation — that lets those teams execute against a shared plan with confidence. Given the visibility of the initiatives in scope, this role reports directly to the CTO and carries executive-level exposure from day one.

Requirements

5+ years of specific, relevant experience leading complex, technical, cross-functional programs — ideally including large-scale software delivery, systems integration, platform modernization, or automation initiatives.
PMP certification (Project Management Professional), or equivalent demonstrated program management rigor.
Track record managing programs with real budget, staffing, and executive accountability — not just coordinating a backlog.
Fluency with both structured (waterfall/stage-gate) and Agile delivery models, and good judgment about which to apply where.
Demonstrated proficiency using LLM tools — Claude Cowork in particular — as a daily productivity multiplier: drafting and maintaining status reports, program plans, and executive updates; synthesizing notes and artifacts across workstreams; and pressure-testing schedules, dependency maps, and RAID logs before they go to stakeholders.
Ability to set up and manage AI projects with scheduled, automated tasks that carry recurring program work — standing status roll-ups, RAID log hygiene checks, milestone and burn-rate monitoring, pre-meeting briefing prep — paired with the judgment to review and own the output rather than forward it unchecked.
Excellent communication skills, written and verbal, with the judgment and range to tailor the same message for an engineer, a VP, and the CEO.
Comfort operating in ambiguity across multiple concurrent, high-visibility initiatives without losing rigor on any of them.
Experience standing up or maturing a PMO function or program-governance model inside an engineering organization.
Hands-on proficiency with program/PPM tooling (e.g., Jira, Confluence, Smartsheet, MS Project, or equivalent).

Nice To Haves

Experience in payroll, HR technology, entertainment/media production finance, or another regulated, operationally complex domain.
Experience managing vendor or systems-integrator relationships on technical delivery programs.
Additional certifications (e.g., PgMP, SAFe, Lean Six Sigma) are a plus but not a substitute for demonstrated delivery track record.

Responsibilities

Establish and maintain scope, schedule, and budget baselines for each assigned program, and maintain a single source of truth for status across contributing teams.
Build and maintain integrated program plans and dependency maps across engineering, product, QA, data, and operations workstreams to sequence work realistically and expose critical-path risk early.
Run the standard program-management cadence (RAID logs, steering committees, change-control processes, milestone gates) proportional to program complexity — without adding process for its own sake.
Track burn against budget and forecast variance early enough for leadership to act on it, not just report it after the fact.
Own the communication rhythm — status reports, steering committee updates, and working sessions — that keep engineering, product, and business stakeholders aligned on status, decisions, and near-term priorities.
Keep updates to the CTO and other executive stakeholders clear, honest, and actionable at every altitude — the same update landing as technical detail for an engineer, a risk-and-tradeoff summary for a VP, and a business-impact headline for the CEO.
Act as the connective tissue between teams that don't naturally talk to each other, so decisions get made once instead of re-litigated in five different meetings.
Identify risks and blockers proactively — before they become schedule or budget impacts — and drive them to resolution or a documented mitigation plan.
Escalate clearly and with the right urgency: know when a blocker needs a Teams/Slack message, when it needs a leadership decision, and when it needs the CTO in the room.
Chase down cross-team dependencies across engineering, infrastructure, vendor, and third-party dependencies before they stall a workstream.
Track program spend and resource allocation against approved budgets in partnership with engineering leadership and finance, and flag resourcing gaps before they cause slippage.
Where applicable, oversee third-party or vendor workstreams (staff augmentation, systems integrators, or specialty vendors), including timeline and deliverable accountability.
Ensure business stakeholders (Payroll Ops, Client Services, Finance, and others touched by these programs) understand what's changing, when, and how it affects their work — reducing surprises at go-live.
Run formal change management (scope changes, timeline shifts, re-sequencing) so decisions are made deliberately and documented, not absorbed silently into the plan.