Job Description

Our mission is simple: to help our customers increase their online sales.

Breadstack is built in Canada to solve the real challenges of cannabis retailers. We give dispensaries one platform that syncs inventory, manages orders, and handles payments, delivery, and fulfillment--all in real time. With seamless POS integrations, SEO-optimized storefronts, live chat, marketing tools, and powerful analytics, we remove manual work so retailers focus on customers. In a regulated market, we bake compliance into every layer--age checks, province rules, secure payments--so our clients can launch and scale confidently. Join us to simplify complexity, boost revenue, and shape the future of cannabis retail commerce.

Role Overview:

As Head of Sales at Breadstack, you own new revenue targets and lead a lean, ambitious team across Canada. You'll refine how we sell to small dispensaries and multi-store operators by building repeatable sales processes, launching high-impact outbound motions, and uniting cross-functional partners around clear messaging. Reporting to the CEO, you'll set the pace for growth, structure, and consistency in our Sales org. This remote-first role requires flexibility across Canadian time zones, with occasional travel (~20%) for client meetings and key events.

What You'll Do

Manage and mentor 2 AEs (plus SDR/BDR support as we scale). Define hiring scorecards, run interviews, and own smooth onboarding and ramp plans. Carry a personal quota. Close strategic deals, model best practices, and drive the team toward sales targets. Design a multi-stage sales methodology for cannabis eCommerce (SMB and mid-market). Build qualification frameworks, CRM automations, playbooks, objection guides, and scalable templates. Launch and optimize outbound programs for single-store and multi-location dispensaries. Partner with Marketing on ICPs, messaging, and campaigns to fuel pipeline growth. Create or collaborate on training materials: product demos, competitive battle cards, negotiation tactics. Align with Marketing on positioning and case studies that resonate. Work closely with Marketing on lead generation strategy and feedback; partner with Customer Success to ensure a seamless Sales?CS handoff; share on-the-ground insights with Product; liaise with RevOps/Finance on forecasts, compensation, and budgets. Build a reliable forecasting model with leading/lagging indicators (pipeline coverage, win rates, sales velocity). Present data-backed updates, defend assumptions, and maintain ?90% forecast accuracy. Act as a trusted advisor to prospects and customers--especially mid-market or strategic accounts. Attend events or client visits to strengthen relationships and gather market insights. Use customer feedback and market trends to guide product enhancements and go-to-market strategy, focusing on POS integrations, fulfillment workflows, and marketing tools. Balance ruthless focus on priorities with strong team morale. Innovate under constraints, stay relentless yet collaborative, and uphold excellence even under pressure.

Who We're Looking For

7+ years in SaaS sales, including 3+ years leading and scaling small-to-medium teams in a high-growth setting. Proven record closing deals relevant to dispensaries (e.g., ACV $5K+ for SMB, larger for multi-store chains) and accelerating cycles (?8-12 weeks). Demonstrated success growing new ARR from ?$1M to ?$3M in a year, with clear examples of which levers moved the needle fastest. Comfortable owning aggressive targets and building repeatable playbooks. Experience building or improving multi-stage sales processes with clear exit criteria, automations, and CRM dashboards. Strong analytics skills: cohort/CAC:LTV analysis, pipeline math, forecast modeling, using metrics weekly to guide actions. Skilled mentor: turning underperformers into quota achievers, documenting playbooks, holding teams accountable. Experienced in spotting coachability and designing structured ramp plans. Effective collaborator with Product, Marketing, Customer Success, and Finance to unblock revenue--able to secure resources or influence priorities with data-driven narratives. Executive presence: comfortable presenting to CEO, leadership team, or board; can field tough questions on forecasts and strategy; maintains forecast accuracy within 10%; able to walk through bottoms-up models in detail. Strategic thinker: can outline a 90-day plan to hit CA$3.5M ARR and map a U.S. expansion roadmap. Innovative under constraints, relentlessly focused while keeping team morale high. Bonus if you have experience or strong interest in cannabis retail tech or regulated eCommerce. Familiarity with HubSpot or Salesforce and outbound tools (Outreach, Apollo) is a plus. Highly organized, data-driven, entrepreneurial, and resilient. Excellent communicator in active voice: concise, persuasive in meetings and writing. Remote-first mindset, able to collaborate across Canadian time zones; occasional travel (~20%) for client or industry engagements.

What We Offer

On-Target Earnings:

$250K per year (depending on experience).

Commission Incentives:

Tiered structure with accelerators and no cap.

Benefits & RRSP Matching:

For full-time employees.

Flexible Work:

Hybrid or fully remote (outside Metro Vancouver) within PST or EST, with reliable internet required.

Employment Options:

Employee or contractor roles available (contractors receive retainer-style pay; some perks vary).

Ready to Join?

If you're energized by fast decision-making and eager to drive growth for cannabis retailers, we want to hear from you. Apply now with your resume/CV and a brief note on how you've generated high-quality leads and closed deals in a SaaS context. Let's shape the future of cannabis retail commerce together.

Job Types: Full-time, Fixed term contract

Pay: $130,000.00-$250,000.00 per year

Additional pay:

Bonus pay Commission pay
Benefits:

Dental care Extended health care Flexible schedule Life insurance Paid time off RRSP match Vision care Work from home
Schedule:

Monday to Friday Weekends as needed
Work Location: Remote