Head of Sales - Vancouver
Job Description
Our client is a Canadian SaaS company supporting cannabis retailers with a fully integrated eCommerce platform designed to simplify operations and drive online sales. The platform streamlines inventory syncing, order management, fulfillment, payments, and compliance across provinces—all in real time. With built-in tools for marketing, SEO, live chat, and analytics, it helps dispensaries scale efficiently while staying compliant in a regulated environment.
They are seeking a Head of Sales to lead new revenue growth and manage a lean, high-performing sales team. Reporting directly to the CEO, this role is responsible for refining the sales strategy, overseeing team performance, and executing against aggressive targets in both the SMB and mid-market segments. This remote-first position requires occasional travel for client meetings and industry events.
Responsibilities:
Lead and grow the sales team, including hiring, onboarding, mentoring, and performance management
Carry a personal quota and lead by example in closing strategic deals
Design and implement a multi-stage sales process tailored to cannabis eCommerce
Develop and optimize outbound sales strategies targeting both single-location and multi-store operators
Collaborate with Marketing on ICPs, messaging, campaign strategy, and lead generation
Build and maintain training resources (playbooks, demos, objection handling, battle cards)
Work cross-functionally with Customer Success, Product, and Finance to ensure alignment and drive revenue
Create and manage a reliable sales forecast based on clear KPIs (win rates, sales velocity, pipeline coverage)
Present data-driven updates to leadership and defend forecast assumptions confidently
Attend key events and client meetings (~20% travel) to deepen relationships and gather market insights
Use customer and market feedback to guide product improvements and inform go-to-market strategy
Requirements
7+ years in B2B SaaS sales, including 3+ years leading and scaling small-to-medium teams
Proven ability to grow new ARR from ~$1M to $3M+ within a year
Experience selling into regulated industries or retail tech, ideally with ACVs in the $5K–$50K+ range
Deep understanding of sales operations: forecasting, CRM optimization, and building repeatable processes
Strong data orientation: ability to analyze CAC:LTV, pipeline health, and conversion metrics
Skilled at coaching sales teams, holding accountability, and designing structured ramp plans
Executive presence with experience reporting to CEOs or boards; confident presenting forecasts and strategic roadmaps
Effective cross-functional collaborator with experience influencing Marketing, Product, and Customer Success
Ability to travel periodically across North America and work flexibly across PST/EST time zones
Experience in cannabis tech or other regulated eCommerce verticals is a strong asset
Familiarity with HubSpot, Salesforce, and outbound tools like Apollo or Outreach is preferred
Compensation: $130,000 base salary + uncapped commission with on-target earnings (OTE) of approximately $260,000.
Please submit all resumes to Amy Hawksworth at Hawksworth@catchrecruitment.com