Strategy & Operations Project Manager

Dragos

4d•$145,000•Remote

About The Position

Dragos is seeking a Senior Project Manager, Strategy & Operations to join the Office of the CEO, reporting directly to the Chief of Staff. This role is the execution engine of the Office of the CEO, responsible for ensuring that strategic decisions, leadership commitments, and cross-functional initiatives are executed with discipline, visibility, and accountability. The Senior Project Manager owns the operational machinery that makes the CEO office run: managing complex initiative portfolios, driving cross-functional coordination, maintaining executive-grade visibility, and ensuring nothing in the portfolio slips, stalls, or loses visibility. The Chief of Staff owns the strategy, relationships, and leadership of the Office of the CEO. The Senior Project Manager owns deep operational accountability across the portfolio, responsible for tracking and execution excellence across all active initiatives. This is a high-ownership, high-impact IC role that frees the Chief of Staff and Executive Leadership team to focus on strategy and decisions, rather than operational overhead. The Senior Project Manager drives outcomes through execution excellence, proactive risk management, flawless coordination, and ensuring that strategic decisions translate into measurable business results. The ideal candidate is a senior, highly structured operator with proven success in managing complex, concurrent enterprise initiatives. They take deep ownership of execution excellence, thrive in ambiguity, can manage multiple high-priority workstreams simultaneously, and have strong judgment about what matters. They're proactive problem-solvers who understand how to unblock cross-functional work, influence without authority, and drive outcomes through operational excellence rather than organizational authority.

Requirements

6–8+ years of experience managing cross-functional projects in a fast-paced enterprise environment, with a demonstrated track record of delivering complex initiatives on time and within scope.
Proven ability to develop and maintain comprehensive project plans, roadmaps, action logs, and status reports that drive executive-level visibility.
Strong stakeholder management skills — able to hold people accountable, surface blockers, and influence across organizational boundaries without direct authority.
Proficiency with project and collaboration tools, including Jira, Confluence, Slack, and Microsoft 365 (Teams, SharePoint, Excel).
Exceptional organizational discipline — this role manages many concurrent workstreams simultaneously and must keep every one of them current.
Strong written communication skills with the ability to translate complex project status into clean, concise executive summaries.
Comfortable operating in ambiguity with minimal direction; able to structure and manage work that is not always neatly defined at the outset.
An AI-native working style is highly important — this role operates inside one of Dragos’s most active AI enablement programs, and the ideal candidate doesn’t just tolerate AI tools but defaults to them. Comfort using AI for research, drafting, synthesis, status reporting, and project tracking is expected from day one.

Nice To Haves

Experience supporting M&A integration, organizational change, or executive-level programs is highly preferred.
PMP, CSM, or equivalent certification preferred.
Experience working in a cybersecurity, SaaS, or high-growth technology company is a strong plus.

Responsibilities

Own project tracking and milestone management for active M&A integrations, including cross-functional workstream coordination, action item tracking, and executive status reporting.
Establish and maintain integration calendars, risk logs, and decision registers that give the Chief of Staff real-time visibility into progress and blockers across all active integrations.
Coordinate with People, Finance, Legal, IT, and GTM teams to surface integration dependencies and drive resolution on open items — escalating to the Chief of Staff when decisions or unblocking require leadership involvement.
Develop standardized intake templates and integration playbooks to accelerate future acquisitions, capturing lessons learned from each integration cycle.
Track all action items and commitments generated from ELT meetings and leadership forums, maintaining a current, complete log that the Chief of Staff can rely on without having to chase status themselves.
Build and maintain project plans for cross-functional initiatives that the Chief of Staff is driving, ensuring timelines, owners, and milestones are documented and current.
Proactively surface risks, timeline slippage, and items at risk of falling through the cracks — bringing them to the Chief of Staff’s attention before they become problems.
Own project execution for company-wide programs managed through the Office of the CEO, for example AI initiatives, cross functional technical projects, etc.
Produce executive-grade status updates, decision trackers, and project dashboards that give leadership clear portfolio visibility without requiring them to chase information.
Manage project intake across the Office of the CEO portfolio: triage incoming requests, assess scope, assign ownership, and ensure every commitment has a plan and an owner.