We are looking for a Director of Technical Program Management to own end-to-end planning and execution across Cyberhaven's most complex, cross-organizational product initiatives. This role is accountable for release predictability, execution visibility, and operating discipline across the entire engineering organization, not a single team or program, but the system of programs that make up Cyberhaven's roadmap. This is an individual contributor role: influence and impact are driven through expertise, judgment, and cross-functional leadership rather than headcount or direct reports. The person in this role is expected to operate as a peer to engineering leadership, shaping strategy and operating cadence at the organizational level while still being hands-on with the planning, tracking, and execution work itself. This role also serves as the primary architect of engineering leadership's monthly and quarterly business reviews, providing decision support, surfacing risk, and driving follow-through across the company's highest-priority engineering programs. This role goes well beyond traditional program management. It requires deep technical fluency to engage credibly with senior engineering leaders and architects, strong executive presence and organizational judgment to shape leadership priorities, and systems-level thinking to turn fragmented operational signals into the metrics, reporting, and AI-enabled automation that let Cyberhaven scale how it plans, tracks, communicates, and reviews technical work. **What you'll do** **Program Leadership and Executive Support** - Own end-to-end planning, execution, and coordination across Cyberhaven's most complex, multi-team, cross-organizational programs, partnering directly with engineering and product leadership - Set the strategy for how Cyberhaven improves predictability in its release model, including how scope changes, readiness risks, and cross-team dependencies are tracked and escalated - Architect and run the engineering operating cadence, including monthly and quarterly business reviews, by consolidating team updates, preparing leadership readouts, and driving follow-through on action items at the executive level - Partner with engineering leadership to translate company and organizational strategy into clear execution plans, success criteria, reporting standards, and operating mechanisms across the entire engineering org - Define and standardize org-wide success metrics across quality, release health, and velocity, driving greater predictability company-wide while enabling team-specific metrics where needed - Build and own the review cadences, status reporting, leadership readouts, and action follow-up systems used to surface execution risk and intervention needs across all teams and programs - Establish data hygiene and governance standards in systems like Jira and related planning artifacts so that release, ownership, status, and progress signals are reliable at scale - Lead the most ambiguous, highest-priority engineering initiatives that require additional structure, executive visibility, and follow-through, often stepping in where no clear owner exists - Act as a thought partner and mentor to other program managers and engineering leaders, raising the bar on operating discipline, accountability, and reporting consistency across the org, without formal management authority **AI-Enabled Automation** - Set the direction for AI-assisted dashboards and reporting workflows that give leadership visibility into program health, release scope, delivery risk, and team performance - Design and build automations that connect tools like Jira, Notion, GitHub, and Slack to surface planning, execution, release, and other delivery signals across the org - Automate recurring program management processes such as status collection, follow-up tracking, review preparation, and stakeholder reporting at scale - Use these workflows to transform release reporting, business review inputs, leadership updates, and recurring status reporting, materially reducing manual status chasing across engineering **Who you are** - 10+ years of experience in Technical Program Management, Release Management, Engineering Operations, or a similar technical cross-functional role, with a track record of operating at Director-level scope as an individual contributor - Demonstrated experience owning end-to-end planning and execution for the most complex engineering initiatives, spanning multiple teams and organizations - Strong technical fluency and systems thinking, especially in engineering process, release workflows, operational reporting, and execution management - Proven ability to drive accountability, coordination, and follow-through across an entire engineering organization without direct authority - Track record of defining success metrics, tracking execution health, and turning operational signals into clear, executive-level reporting and decision support - Excellent written and verbal communication skills, including experience owning monthly and quarterly business reviews, executive-facing updates, and cross-functional status reporting - Deep familiarity with Jira-based workflows, reporting, and process hygiene at scale - Strong judgment in prioritization, escalation, and leadership support in ambiguous or fast-moving situations, with the credibility to influence senior stakeholders - Comfort using automation and AI to improve reporting quality, operating efficiency, and recurring workflow execution - Experience owning QBRs, executive reporting, and engineering metrics programs at the org or company level - Familiarity with DORA-style metrics, SLO/SLA thinking, release hygiene, and delivery scorecards - Experience building AI-assisted dashboards, automations, or reporting systems - Experience working in security, SaaS, endpoint, platform, or infrastructure-heavy environments - Experience supporting globally distributed engineering organizations - Prior experience operating at Director or Principal level as an individual contributor (not a people manager)