Head of SMB Retail Sales

Shopify's Retail business is one of the fastest growing parts of the company,. In SMB, there is an existing sales motion in market today, but it needs to be optimized, scaled, and pressure-tested against some big open strategic questions. This person will own the acquisition engine for SMB retail, leading a team that is expected to grow in the near term. You will operate as a second-line leader managing a group of frontline managers. If you have spent time selling POS and retail solutions and want to bring that expertise to a platform with massive reach and ambition, this is the role. Key Responsibilities Own the full SMB retail acquisition number and hold yourself accountable for hitting it Lead and develop a team of 4-5 frontline sales managers and approximately 40-50 individual contributors Define the growth plan for the team, including headcount modeling, territory design, and ramp timelines Optimize the existing sales motion by identifying bottlenecks, fixing conversion gaps, and raising the bar on execution Partner cross-functionally with product, marketing, and partnerships to shape the retail go-to-market Build the operating cadence for the team: forecasting, pipeline reviews, coaching rhythms, and performance management Qualifications Experience leading sales teams in the retail technology or POS space; you have sold to SMB merchants before Operated as a second-line sales leader managing frontline managers, not just individual contributors Built or scaled a sales team through a period of meaningful growth, not just maintained one Strong strategic thinking — able to take ambiguous, open-ended business questions and turn them into a plan Comfortable with data — you use pipeline and funnel metrics to diagnose problems and drive decisions Nice to have Experience standing up a field sales or in-person sales motion from scratch Experience operating in a high-growth environment where the playbook was still being written