At Backcountry, our mission is to connect people to their passions. Our four online stores—Backcountry, Competitive Cyclist, MotoSport and, SteepandCheap—aim to supply our customers with the gear, knowledge, and inspiration necessary to get out there and chase down life’s greatest moments. We do this by providing the biggest and best assortment of premium outdoor products, superior shopping experience, personalized Gearhead expertise, lightning-fast and accurate fulfillment, and inspirational, informative, and community-centered content.
Backcountry is building the most trusted, expert-guided destination for outdoor gear—and doing it with speed, discipline, and clarity. We’re looking for an Executive Assistant, Strategy & Operations to support the President and select executives as a trusted partner, operational amplifier, and systems thinker.
This is not a traditional administrative role. It’s a Chief of Staff–lite position for someone who sees around corners, uses AI and automation to eliminate friction, and helps leaders focus their time on what drives the most impact. You’ll work at the center of the business—supporting execution against our strategy while raising the operating bar across leadership workflows.
If you’re energized by ownership, structure, and building smarter ways to work in a high-growth environment, this role is for you.
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.
We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.
The CSC family of brands provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, provincial, state or local laws.
The CSC family of brands is committed to providing reasonable accommodations for qualified individuals with disabilities in our job application procedures. If you need assistance or an accommodation due to a disability, please contact [email protected].
