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ashby

Chief of Staff, Engineering

Cyberhaven
Remote, USA
Full-time
Senior · 7+ years experience
Remote
USD 200000-220000 yearly / year
Discovered 1 months ago
JiraNotionGitHubSlack

Full Job Posting

Strategic Partnership and Executive Support

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

Program and Project Management

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

Data and Metrics-Driven Operations

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

AI-Forward Automation

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

Who you are

7+ years of experience in a role combining program management, project management, and executive or leadership support

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

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

Joining Cyberhaven means joining the team building Data Security for the Agentic Enterprise. Traditional tools fall short. Cyberhaven traces the full lifecycle of your data, adapting protection to changing context, so protection moves with the way people actually work, not against it. AI Changed Work. We Protect It. Backed by $250M from leading investors like Khosla and Redpoint, our team includes leaders who built industry-defining technologies at CrowdStrike, Palo Alto Networks, Meta, Google, and more. This role lets you shape the future of data security, working alongside people driven to protect workflows, not just data, for customers who cannot afford to slow down to stay safe.

AI Tools Disclosure: As part of Cyberhaven's hiring process, we use recruiting tools that include AI-powered features to help with tasks like scheduling, note-taking, workflow automation, and other recruiting activities ("AI Tools"). The AI Tools may process information you provide during the application and interview process. When AI-assisted interview note taking is used, candidates are notified in advance and have the option to opt out of the AI-assisted interview note taking.

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.

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