TRAILS

Operations

• 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

Director of Strategic Operations