Director of Strategic Operations - Apply by 5/1/26

THE ROLE

We're looking for a highly organized, proactive, and driven Director of Strategic Operations to serve as the organizational multiplier of our leadership team. This is a high-impact, high-visibility role at the center of a fast-scaling organization — ideal for someone who thrives in dynamic environments, loves bringing order to complexity, and takes pride in making leaders and teams more effective.

You'll work directly with the CEO and leadership team to ensure the organization runs smoothly, information flows clearly, and nothing falls through the cracks. You'll be the person who sees what's coming before anyone else does, and has already built the system to handle it.

This is not a coordinator role. You'll have real ownership, real visibility, and real impact on how the organization operates and scales. If you're the kind of person who reads a messy process and immediately starts mentally redesigning it — and then actually does something about it — we want to meet you.

THE RESPONSIBILITIES

Executive & Leadership Team Support (30%)

• 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
• Culture, Trust & Organizational Health — reinforces culture and does the invisible work of keeping a remote team connected to each other

Meeting Operations (20%)

• 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

Presentations & Communications (20%)

• 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
• Own the editing, formatting, and quality control of key documents and presentations

Information & Knowledge Management (20%)

• 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
• Develop and own the org's shared knowledge bases

Events & Retreat Logistics (10%)

• 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
• Manage logistics budgets and timelines, ensuring seamless experiences for all attendees
• Anticipate and resolve logistical challenges before they become problems

THE PERSON

Our experience suggests that the following types of professional experiences lend themselves to this work:

• 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

Our experience suggests that the following types of skills lend themselves well to this work:

• A natural operator. You love building systems, streamlining processes, and creating order from chaos. You get energy from making things run smoothly.
• A self-starter. You don't wait to be asked. You see what's needed, take initiative, and follow through — even when the path isn't fully defined.
• An anticipator. You're always two steps ahead. You think proactively about what leaders need before they know they need it, and you've already started working on it.
• A strong communicator. You're clear, concise, and effective — whether in writing, in a meeting, or managing up and across the organization.
• Highly organized under pressure. Multiple competing priorities don't rattle you. You know how to triage, prioritize, and execute.
• Mission-driven and adaptable. You thrive in fast-paced, rapidly scaling organizations and are excited to grow alongside the company.
• Automation-first thinker in the service of people. Loves leveraging tech including AI.
• Low ego, high ownership. Leans in/if something important needs doing and no one's doing it, that's enough.

TRAILS offers a comprehensive benefits package including medical, dental, and vision as well as a 403B with a safe harbor match and short and long term disability. We offer a generous holiday and paid time off package.