Director of Strategic Operations

TRAILS

Director of Strategic Operations managing organizational systems and support for TRAILS' leadership team. Anticipating needs and driving efficiency in a rapidly scaling environment with a commitment to equity.

Posted 4/14/2026full-timeRemote • 🇺🇸 United StatesLead💰 $127,155 - $134,219 per yearWebsite

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

medical, dental, and vision
403B with a safe harbor match
short and long term disability
generous holiday and paid time off package

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

project managementworkflow automationsystems designdata trackingOKRsinformation architecturedocumentation managementevent planningstakeholder managementnarrative clarity

Soft Skills

strategic partnershipanticipation of needsaccountabilityfacilitationalignmentcommunicationproblem-solvingorganizational effectivenesscollaborationlogistical planning