Head of Field Sales

Responsibilities

• Own end-to-end field sales operations, including hiring, training, performance management, territory design, and partner relationship management
• Build and manage high-performing field sales team across multiple retail locations, with direct accountability for application volume and partner satisfaction
• Design and implement scalable field sales infrastructure: territory planning, coverage models, visit cadence, performance dashboards, and coaching frameworks
• Establish rigorous performance management systems with clear metrics, scorecards, and data-driven feedback loops
• Develop training programs to keep field reps fluent in product knowledge, technical support, and customer service best practices
• Build strong relationships with partner leadership and store teams, acting as primary point of contact for field operations
• Analyze unit economics and performance trends to identify improvement opportunities and optimize team efficiency
• Collaborate with cross-functional stakeholders (general managers, finance, operations, tech) to address tooling gaps and operational needs
• Set and maintain high performance bar while building a culture of accountability, ownership, and continuous improvement

Qualifications

• 8–12 years of leadership experience in field sales, retail operations, or territory management, with proven track record of building teams from scratch
• Demonstrated success designing and scaling field sales operations, including territory planning, cadence design, coverage modeling, and performance infrastructure
• Strong analytical skills with experience building dashboards, scorecards, and performance reporting systems (tools agnostic)
• Deep understanding of field sales unit economics, performance metrics, and how to move numbers through coaching and process improvement
• Exceptional communication skills with ability to tailor messaging for executive stakeholders, partner leadership, and frontline team members
• Builder mindset: comfortable with ambiguity, self-sufficient, and able to create structure where none exists
• High ownership mentality: treat the function as if you own it, with personal accountability for results
• Experience managing high-travel roles and teams distributed across multiple locations
• Willing to travel 50–75% of the time to support team and maintain partner relationships

Nice-to-Haves

• Experience in fintech, payments, or financial services (especially credit card partnerships or retail banking)
• Background at companies with strong retail presence or field sales models
• Experience managing performance in commission-based or variable compensation environments
• Familiarity with coaching and developing geographically distributed teams

Perks & Benefits

• Competitive compensation and equity packages
• Leading configured work computers of your choice
• Flexible paid time off
• Fully covered, high-quality healthcare, including fully covered dependent coverage
• Additional health coverage includes access to One Medical and the option to enroll in an FSA
• 20 weeks of paid parental leave for the primary caregiver and 8 weeks for all new parents
• Access to industry-leading technology across all of our business units