Retail Lead, Sales Development

Accountabilities:

• • Lead, coach, and develop a team of Retail Sales Development Representatives, helping them consistently achieve quarterly qualified meeting and sales targets.
  • Provide hands-on coaching around sales best practices, cold outreach, prospect qualification, retail trends, and eCommerce dynamics.
  • Monitor business and industry trends and translate insights into actionable coaching opportunities and sales-process improvements.
  • Track sales activity, funnel performance, and conversion metrics to identify opportunities to improve efficiency and accelerate retailer acquisition.
  • Establish and optimize activity metrics, prospecting strategies, sales processes, and collateral to help the team reach independent retailers more effectively.
  • Build and maintain relationships with high-value retailer prospects, participating directly in customer conversations and key stages of the sales cycle when appropriate.
  • Support the team in closing small-business opportunities and converting qualified prospects into long-term retail partners.
  • Partner closely with cross-functional teams to create scalable processes that strengthen retailer acquisition and support broader business growth.
  • Identify operational gaps and implement practical improvements in a fast-paced, transactional sales environment.
  • Promote a culture of accountability, continuous learning, experimentation, and high performance across the sales development organization.

  Requirements:

  • Demonstrated history of exceeding sales goals and quotas in a sales or business development environment.
  • Experience managing sales teams, or approximately 3–4 years of experience in sales or business development, preferably within eCommerce or a related technology environment.
  • Proven experience coaching, mentoring, and developing early-career sales professionals.
  • Strong understanding of sales funnels, pipeline management, activity metrics, and data-driven sales optimization.
  • Demonstrated success implementing and coaching cold-outreach strategies and improving sales-development performance.
  • Strong analytical and process-oriented mindset, with the ability to turn sales data and market trends into actionable improvements.
  • Excellent communication, coaching, collaboration, and relationship-building skills.
  • Ability to work effectively across functions and influence stakeholders in a high-growth, rapidly changing environment.
  • Creative, resourceful problem-solving approach with a strong bias toward action and measurable outcomes.
  • Experience selling to small and medium-sized businesses is highly valuable.
  • Background in retail, eCommerce, marketplaces, or technology-enabled commerce is preferred.
  • Ability to work remotely and remain effective in a flexible, distributed work environment.

  Benefits:

  • Remote-first flexibility, with employees empowered to work where they are most productive while maintaining connection through in-person team events.
  • Competitive location-based compensation.
  • Canadian base salary range of $112,500–$118,750 CAD for eligible Canadian locations.
  • Target on-target earnings (OTE) range of $149,000–$157,500 CAD, combining salary and sales incentive compensation.
  • Sales Incentive Plan with variable compensation tied to individual sales performance.
  • Eligibility for a new-hire equity grant and potential annual equity refresh grants.
  • Competitive benefits designed to support employees' overall well-being and professional needs.
  • Opportunities to work in a high-growth environment with significant ownership and cross-functional exposure.
  • Inclusive culture that values diverse perspectives, collaboration, innovation, and continuous development.