Director of Strategic Operations
TRAILS
full-time
Posted on:
Location Type: Remote
Location: United States
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Salary
💰 $127,155 - $134,219 per year
Job Level
About the role
- Serve as a strategic partner to the CEO, anticipating needs and removing friction before it surfaces
- Manage the CEO's priorities, follow-up items, and key decisions — ensuring nothing gets lost
- Build and maintain organizational systems that support the leadership team's effectiveness
- Automation & Systems Design — this person builds workflows — in service of people, not instead of them and reduces repetitive tasks.
- Track open action items, decisions, and commitments across the leadership team and drive accountability for follow-through
- Own the design, facilitation, and follow-up for all leadership team meetings — setting agendas, running the meeting rhythm, and capturing clear next steps
- Manage meeting cadences across the organization to ensure time is used intentionally and productively
- Facilitate working sessions that drive alignment and decisions, not just status updates
- Project-manage the development of all high-stakes decks, including board presentations, all-staff meetings, and leadership team materials
- Collaborate with leaders and stakeholders to gather content, ensure narrative clarity, and manage timelines from first draft through final delivery
- Design and maintain the organization's systems for tracking data, OKRs, and key metrics across teams
- Build and steward documentation systems that keep institutional knowledge organized, accessible, and up to date
- Lead end-to-end planning and execution for staff events (1-2 times per year), and leadership retreats (2-3 times a year) — from venue selection and vendor coordination to run-of-show and post-event wrap-up
- Anticipate and resolve logistical challenges before they become problems
Requirements
- 5+ years of experience in operations, chief of staff, executive support, program management, or a related role
- Experience in a high-growth startup or scale-up environment
- Proven ability to manage complex projects with multiple stakeholders and tight timelines
- Strong proficiency with productivity and collaboration tools (Google Workspace, Notion, Airtable, Slack, or similar)
- Experience building and maintaining organizational systems — information architecture, tracking dashboards, documentation — from the ground up
- Demonstrated experience in planning and leadership team events or off-sites
- Comfort working directly with and managing up to senior leaders, and working across all levels of an organization.
Benefits
- medical, dental, and vision
- 403B with a safe harbor match
- short and long term disability
- generous holiday and paid time off package
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
project managementworkflow automationsystems designdata trackingOKRsinformation architecturedocumentation managementevent planningstakeholder managementnarrative clarity
Soft Skills
strategic partnershipanticipation of needsaccountabilityfacilitationalignmentcommunicationproblem-solvingorganizational effectivenesscollaborationlogistical planning