Chief of Staff, Engineering

This is a fully remote position, open to applicants in Florida, +2 more states.

📋 Description

• Serve as a trusted advisor and thought partner to engineering leadership.

• Convert strategic priorities into actionable plans, defining success criteria and operational frameworks.

• Manage the operating cadence for engineering leadership, including staff meetings, monthly and quarterly business reviews, organizational planning, and leadership offsite events.

• Develop agendas, prepare necessary materials, and ensure follow-through on decisions and action items.

• Advocate for engineering leadership priorities throughout the organization.

• Coordinate alignment among engineering, product, and go-to-market teams on significant initiatives.

• Create communications for executives, prepare content for board and all-hands meetings, and provide cross-functional updates.

• Assist with headcount planning, organizational design, and prioritization trade-offs.

• Plan, execute, and harmonize complex programs and strategic projects across multiple teams.

• Monitor changes in scope, readiness risks, and dependencies across teams.

• Establish review cadences, status updates, and systems for tracking actions.

• Enhance Jira data hygiene and governance.

• Establish and standardize metrics related to quality, release health, team velocity, and overall team health.

• Generate data-driven reports and decision support for engineering leadership.

• Take ownership of metrics and narratives for monthly and quarterly business reviews.

• Develop AI-assisted dashboards and reporting workflows.

• Integrate Jira, Notion, GitHub, and Slack through automation.

• Automate the collection of status updates, tracking follow-ups, preparing reviews, and reporting to stakeholders.

• Enhance inputs for business reviews and leadership updates while minimizing manual status tracking.

⛳️ Requirements

• A minimum of 7 years of experience in a role that blends program management, project management, and executive or leadership support.

• Previous experience as Chief of Staff or in Engineering Leadership is an advantage.

• Possess a strong executive presence and sound judgment.

• Make data-driven and metrics-oriented decisions.

• Ability to foster accountability, coordination, and follow-through without direct authority.

• Excellent written and verbal communication skills.

• Experience managing monthly and quarterly business reviews, executive updates, and cross-functional reporting.

• Comfort with automation and AI technologies.

• Good judgment in prioritization, escalation, and providing leadership support.

• Familiarity with managing QBRs, executive reporting, all-hands content, or organizational planning processes.

• Knowledge of DORA-style metrics, SLO/SLA principles, release hygiene, and delivery scorecards.

• Experience in building AI-assisted dashboards, automation, or reporting systems.

• Background in security, SaaS, endpoint, platform, or infrastructure-heavy environments.

• Experience supporting globally distributed engineering teams.

• Technical or program management background transitioning into a Chief of Staff or executive operations position.

• Authorized to work in the United States; must be legally able to work in the United States without sponsorship now or in the future.

🏝️ Benefits

• Equity.

• Bonus plan.

• Market-competitive compensation.

• Compensation adjustments based on geographic location.

• Option to opt-out of AI-assisted interview note-taking.

• Equal opportunity employer.