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.
The Head of Group Sales is a revenue execution leader with true “rainmaker” credibility — someone who has personally closed large, complex B2B deals and now excels at scaling disciplined team performance.
This is not a strategy design role — the strategy, tools, and opportunity already exist. The mandate is execution.
You will lead and scale Backcountry’s Group Sales program by driving structured pipeline management, enforcing accountability, increasing per-rep output, and materially expanding revenue contribution across the team.
This is a player–coach role, but your primary value is translating growth strategy into measurable, repeatable execution. You will step into major deals when needed, but your core impact comes from raising performance standards, improving forecast accuracy, and ensuring consistent revenue delivery across the team. This role is challenging – above and beyond the day-to-day responsibilities, you’ll have a big role within a fast-paced team.
This position will report into the Chief Growth Officer.
What You Get to Do:
Revenue Execution & Performance Leadership
Serve as a revenue execution leader with “rainmaker” credibility — modeling the behaviors required to win large, complex B2B deals
Translate existing growth strategy into disciplined, repeatable team execution
Drive structured pipeline management and enforce CRM rigor and forecasting accuracy
Increase per-rep productivity through clear activity standards, performance tracking, and coaching
Personally step into high-value or at-risk deals when needed to secure outcomes
Raise the performance bar by setting clear expectations for outreach volume, conversion quality, and close rates
Ensure consistent enforcement of process, not just creation of process
Leadership & Team Development
Lead, coach, and develop a team of 5–8 Group Sales Account Managers
Drive a high-performance, accountable, results-oriented sales culture
Conduct structured 1:1s, pipeline reviews, and deal strategy sessions
Provide direct coaching on outbound prospecting, objection handling, pricing strategy, and closing
Hire and onboard
Revenue Ownership & Output Scaling
Own and materially increase total revenue contribution from the Group Sales channel
Drive predictable performance through structured pipeline reviews and deal inspection
Improve per-rep output through accountability, coaching, and performance management
Identify performance gaps quickly and implement corrective action plans
Ensure disciplined enforcement of sales methodology, pricing strategy, and negotiation standards
Maintain personal credibility by continuing to engage in complex, strategic deal-making
AI-Enabled Sales Execution
Implement and oversee AI-driven workflows to increase productivity and deal velocity
Write clear prompts, validate outputs, and iterate based on rep feedback
Drive consistent adoption of tools that improve quality and efficiency
Partner with leadership to scale modern, tech-enabled sales systems
Data-Driven Sales Operations
Own funnel metrics and pipeline health across the team
Improve CRM discipline, reporting consistency, and forecasting accuracy
Build scalable processes for lead routing, opportunity tracking, and follow-up
Identify opportunities to shorten sales cycles and increase conversion
Cross-Functional Collaboration
Partner with merchandising, operations, and vendor teams to support inventory planning and special orders
Ensure seamless execution and high-quality service for business accounts
Help shape long-term strategy for Group Sales within broader brand initiatives
What You Bring to the Role:
7+ years of B2B, outbound, or account management sales experience
2+ years of sales leadership experience in a quota-carrying environment
Demonstrated success closing complex, high-value strategic accounts
Proven track record of consistently meeting or exceeding revenue targets
A true player–coach mindset — you enjoy leading a team but still love to sell
Strong negotiation skills and executive-level relationship management ability
Experience building structure, process, and accountability within sales teams
Comfort operating in fast-paced, performance-driven environments
Retail, ecommerce, or outdoor industry experience preferred
Who This Role Is For:
A proven B2B “rainmaker” who has personally closed large, complex deals and now wants to scale impact through a team
A revenue execution leader who values accountability, discipline, and measurable output
Someone who thrives on performance management and raising standards — not just building ideas
A sales leader who understands that consistent enforcement drives predictable growth
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.
Our preference is for candidates who reside near our hub in Toronto.
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.
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.
Washington state applicants only: If you believe that this job posting does not comply with applicable Washington state law, please notify us by sending an email to [email protected].
It is unlawful in Massachusetts to require or administer a lie-detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.
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].
