[Hiring] Head of Field Sales @Imprint

Role Description

As Head of Field Sales, you will own and scale Imprint's in-house field sales function. This is a senior leadership role with full accountability for field team performance, partner relationships, and operational excellence across retail locations.

You will lead a high-performing field sales team, building the systems, processes, and culture needed to deliver measurable results for Imprint's most important strategic partnerships, and scale the team to support new partnerships as Imprint grows. This role requires a builder mindset, deep ownership, and the ability to operate with autonomy in a high-stakes, confidential transition.

What Success Looks Like in the First 90 Days

• Established clear performance management framework with KPIs tied to application volume, merchant spend, store-level engagement, and partner feedback.
• Built trust with store teams so visits are valued and employees look forward to field rep engagement.
• Defined operating cadence including visit frequency, agenda structure, performance reviews, coaching rhythms, and escalation protocols.
• Created prioritized roadmap of operational and tooling gaps, with clear plan to leverage Imprint's full tooling suite for field team enablement.

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 Have

• 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.

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, stemming from our philosophy that we should invest in resources for our team that foster innovation, optimization, and productivity.