Chief of Staff, Engineering

Cyberhaven • Boston, MA

11d • $200,000 - $220,000 • Hybrid

About The Position

Cyberhaven is looking for a Chief of Staff for Engineering to collaborate and perform as an operating partner and force multiplier for engineering leadership, driving operating cadence, cross-organizational execution, and data-driven decision making across the entire engineering org. This role is accountable for turning strategic priorities into clear execution plans, and for giving leadership the visibility, metrics, and follow-through they need to run engineering like a well-oiled machine.
This is a hybrid role that blends program management, project management, and executive operations: the person in this role will sit close to engineering leadership, represent their priorities across the org, and be the connective tissue between strategy and day-to-day execution. Influence and impact come from judgment, trust, and cross-functional credibility rather than direct authority.
This role also serves as the primary architect of engineering leadership's monthly and quarterly business reviews, all-hands content, org planning, and leadership offsites providing decision support, surfacing risk, and driving follow-through on the company's highest-priority engineering initiatives.
This role goes well beyond traditional chief of staff work. It requires strong executive presence to represent leadership credibly in front of the org and external stakeholders, deep comfort with data and metrics to turn fragmented signals into clear decision support, and an AI-forward mindset to automate the reporting and operating mechanisms that let Cyberhaven scale how it plans, tracks, communicates, and reviews its work.

Requirements

• 7+ years of experience in a role combining program management, project management, and executive or leadership support
• Strong executive presence and the judgment to represent leadership credibly across the org and with external stakeholders
• A data-driven, metrics-driven approach to decision making, with the ability to turn fragmented operational signals into clear reporting and insight
• Proven ability to drive accountability, coordination, and follow-through across engineering and product teams without direct authority
• Strong written and verbal communication skills, including experience owning monthly and quarterly business reviews, executive-facing updates, and cross-functional status reporting
• Comfort using automation and AI to improve reporting quality, operating efficiency, and recurring workflow execution
• Good judgment in prioritization, escalation, and leadership support in ambiguous or fast-moving situations
• Experience owning QBRs, executive reporting, all-hands content, or org planning processes
• 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 transitioning from a technical or program management background into a Chief of Staff or executive operations role

Nice To Haves

• Prior experience as a Chief of Staff or Engineering Leadership roles a plus

Responsibilities

• Act as a trusted advisor and thought partner to engineering leadership, helping translate strategic priorities into clear execution plans, success criteria, and operating mechanisms across the org
• Own the engineering leadership operating cadence, including staff meetings, monthly and quarterly business reviews, org planning, and leadership offsites, setting agendas, preparing materials, and driving follow-through on decisions and action items
• Represent engineering leadership's priorities across the organization, ensuring alignment between engineering, product, and go-to-market teams on key initiatives
• Prepare executive-facing communications, board and all-hands content, and cross-functional updates on behalf of engineering leadership
• Act as a sounding board and extension of leadership on sensitive or ambiguous organizational topics, including headcount planning, org design, and prioritization tradeoffs
• Build trust and credibility across engineering, product, and business stakeholders to effectively drive alignment without formal authority
• Own end-to-end planning, execution, and coordination across complex, multi-team programs and time-sensitive strategic projects for engineering leadership
• Improve predictability in Cyberhaven's release and planning model by tracking scope changes, readiness risks, and cross-team dependencies
• Build and maintain review cadences, status updates, and action follow-up systems that surface execution risk and areas needing intervention across teams and programs
• Support high-priority or ambiguous engineering initiatives that need additional structure, executive visibility, and follow-through, often stepping in where no clear owner exists
• Improve data hygiene and governance in systems like Jira and related planning artifacts so that ownership, status, and progress signals are reliable
• Define and standardize success metrics across quality, release health, velocity, and team health to drive greater predictability and accountability
• Turn operational signals from across the org into clear, data-backed reporting and decision support for engineering leadership
• Own the metrics and narrative behind monthly and quarterly business reviews, ensuring leadership has accurate, timely, and actionable data
• Bring a data-driven lens to org health, from delivery metrics to team sentiment, to help leadership spot risk early
• Build AI-assisted dashboards and reporting workflows that improve visibility into program health, release scope, delivery risk, and team performance
• Create automations that connect tools like Jira, Notion, GitHub, and Slack to surface planning, execution, release, and other delivery signals
• Automate recurring chief of staff and program management processes such as status collection, follow-up tracking, review preparation, and stakeholder reporting
• Use these workflows to improve business review inputs, leadership updates, and recurring status reporting while reducing manual status chasing

Benefits

• Cyberhaven is committed to creating a diverse environment and is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed