[Hiring] Director of Strategic Operations @TRAILS

Role Description

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.

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 — build workflows in service of people, reducing repetitive tasks.
  • Track open action items, decisions, and commitments across the leadership team and drive accountability for follow-through.
  • Reinforce culture and do the invisible work of keeping a remote team connected.
• Meeting Operations (20%)
  • Own the design, facilitation, and follow-up for all leadership team meetings.
  • Manage meeting cadences across the organization to ensure time is used intentionally and productively.
  • Facilitate working sessions that drive alignment and decisions.
• Presentations & Communications (20%)
  • Project-manage the development of all high-stakes decks, including board presentations and leadership team materials.
  • Collaborate with leaders and stakeholders to gather content and manage timelines.
  • 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.
  • Build and steward documentation systems that keep institutional knowledge organized and accessible.
  • Develop and own the org's shared knowledge bases.
• Events & Retreat Logistics (10%)
  • Lead end-to-end planning and execution for staff events and leadership retreats.
  • Manage logistics budgets and timelines, ensuring seamless experiences for all attendees.
  • Anticipate and resolve logistical challenges before they become problems.

Qualifications

• 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 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.

Requirements

• A natural operator who loves building systems and streamlining processes.
• A self-starter who takes initiative and follows through.
• An anticipator who thinks proactively about what leaders need.
• A strong communicator who is clear, concise, and effective.
• Highly organized under pressure with the ability to triage and prioritize.
• Mission-driven and adaptable in fast-paced environments.
• Automation-first thinker who loves leveraging tech including AI.
• Low ego, high ownership approach.

Benefits

• Salary range: $127,155 - $134,219.
• Comprehensive benefits package including medical, dental, and vision.
• 403B with a safe harbor match.
• Short and long term disability coverage.
• Generous holiday and paid time off package.

Application Notes

• Application Deadline: The priority deadline for this role is Friday, May 1st.
• Travel required up to 20%.
• We are only considering applicants who are legally authorized to work in the United States.
• TRAILS employees may be required to undergo a background check.

Our Commitment to Diversity, Equity, & Inclusion

Addressing inequities in access to evidence-based mental health care is intrinsic to the TRAILS mission. We encourage applicants who can positively contribute to this commitment, particularly if your voice represents a historically excluded perspective.