Executive Assistant, Strategy & Operations

How This Role Drives Backcountry’s Strategy

• This role directly enables Backcountry’s operating system:
• Be Excellent: Create leverage through AI-driven workflows, disciplined prioritization, and operational rigor.
• Be the Starting Point & Destination: Help leaders focus time and energy on customer impact, CLTV, and end-to-end experience.
• Be Everywhere: Support scale by improving how information flows, decisions are made, and initiatives move forward.
• This position will report into the President.

Executive Partnership & Leverage

• Act as a strategic extension of the executives you support—anticipating needs, prioritizing decisions, and protecting focus.
• Own a very dynamic calendar. Manage heavy volume of meetings across time zones. Book, rebook and cancel meetings as priorities change. Communicate changes.
• Use AI and automation to increase leverage. Apply tools like ChatGPT, Claude, Gemini, and others to draft communications, summarize information, create checklists, and streamline scheduling workflows. Set up and maintain simple automations (rules, zaps, shortcuts, scripts, etc.) that reduce repetitive work and help leadership stay on track.

Strategy & Initiative Support

• Support key company initiatives by tracking priorities, milestones, and cross-functional dependencies.
• Partner on leadership planning, offsites, and board preparation with operational discipline.
• Help translate strategy into clear actions by improving visibility, follow-through, and accountability.

Information Flow & Decision Support

• Serve as a central point for inbound information—filtering, prioritizing, and escalating appropriately.
• Draft and edit executive communications and presentations with clarity and confidence.
• Ensure the right information reaches the right stakeholders at the right time.

Trust, Judgment & Ownership

• Handle highly sensitive and confidential information with discretion and sound judgment.
• Represent executive intent accurately and professionally in interactions across the business and externally.
• Operate with a high bar for quality, clarity, and accountability.

What you bring:

• 5–8+ years of experience supporting senior leaders in a fast-paced, high-growth or complex organization.
• Strong business judgment and the ability to prioritize based on impact, not urgency.
• AI curious and automation-minded. You already use AI tools (e.g., ChatGPT, Claude, Gemini, n8n, Zappier, etc.) in your work or personal life. You enjoy experimenting with new tools, setting up automations, and continuously improving your systems.
• Exceptional organizational, communication, and synthesis skills. You notice small details that prevent big problems. You handle sensitive information with confidentiality and professionalism. You communicate clearly and succinctly in writing and verbally.
• Ability to connect dots across teams, anticipate risks, and proactively solve problems.
• Calm, adaptable, and effective amid shifting priorities.
• Passion for the outdoors and alignment with Backcountry’s customer-first, expert-led mission is a plus.

What’s in it for you? Joining Backcountry isn’t just about having a seat at the table—it’s about helping redesign the table entirely. You’ll be challenged, stretched, and supported as you grow faster than you thought possible. In addition to competitive compensation, we offer:

• Executive Access: Work directly with brand CEOs and senior leadership, solving real business problems and earning mentorship from top operators. 
• AI-First Skill Building: Get hands-on with the most advanced AI tools in the market. From automation to prompt engineering, you’ll build a modern tech stack that sets you apart in any industry. 
• Accelerated Career Path: High performers are quickly entrusted with greater responsibility, new challenges, and leadership opportunities across our portfolio of brands. 
• Competitive benefits:  Paid time off policies, 401(k)/RRSP match, medical/dental/vision and a variety of supplemental policies, and employee discounts at our portfolio companies

Our interview process:

• 📞Step 1: If you align with our vision and meet the qualifications, we’ll reach out to schedule a conversation and introduce Backcountry. 
• 🧠Step 2: You’ll complete a short AI or product-building challenge so we can understand how you approach problems and execution. 
• 💬Step 3: Participate in deep-dive interviews with Backcountry leadership focused on your experience, product mindset, and operational thinking. 
• 📩Step 4: Offer. We’ll move fast for the right candidate.