Director of Sales

Location: Remote (U.S.-based)

Team: Revenue

Type: Full-Time, Employee

Our Story

At Endear, we’re building the first modern CRM for retail teams—starting with the frontline. Our software empowers sales associates to have more personal, effective conversations with customers through AI-powered tools that drive measurable revenue.

Despite retail being 6x larger than eCommerce, most platforms overlook the in-store experience. We’re changing that. We’re here to help brands like Gorjana and Reformation turn real customer relationships into growth powered by intuitive software and thoughtful design.

Position Overview

As we enter our next stage of growth, we’re ready to take our sales engine from strong and steady to truly scalable, and we’re looking for a proven sales leader to lead the way.

As Director of Sales, you’ll lead Endear’s high-performing sales team and own the revenue strategy for our flagship clienteling product. You’ll inherit a well-built foundation with strong processes, a mature product, and a talented team of five, and elevate it with greater predictability, structure, and growth discipline.

Reporting directly to the CEO, you’ll manage all aspects of sales leadership, including forecasting, team performance, process improvement, and revenue ownership. You’ll also partner closely with our Head of Sales (Casey Drake), who is transitioning to a “zero-to-one” role focused on launching new product lines.

This is a leadership role without an individual quota; your team’s success measures your success. The ideal candidate is a process-oriented, hands-on leader who thrives in data, structure, and coaching.

What You’ll Accomplish

In your first 6 months, you’ll…

• Lead a team of five sales reps to consistently hit quota and maintain strong revenue performance.
• Build confidence in forecasting accuracy and establish a predictable weekly, monthly, and quarterly cadence.
• Partner with our sales consulting partner to review and refine sales processes, one-on-ones, and deal management.
• Begin quarterbacking larger, more complex deals to support team close rates.

In your first year you’ll…

• Elevate the sales team to its next level of performance through coaching, process improvements, and smart hiring.
• Fully own revenue operations, including forecasting, pipeline visibility, and conversion analysis.
• Strengthen sales reporting and analytics to provide clarity and accountability across the funnel.
• Partner with leadership to inform go-to-market strategy and future sales org design.

You’ll Thrive in This Role If You…

Have Experience With

• Leading B2B SaaS sales teams (ideally 5–10 reps) with SMB or mid-market customers.
• Managing full-cycle sales with ARR targets between $500K–$3M+ per rep or team.
• Coaching reps through structured one-on-ones, pipeline reviews, and deal strategy.
• Implementing repeatable, scalable sales processes and forecasting frameworks.
• Driving predictable performance through data-driven management and accountability.
• Collaborating cross-functionally with marketing and product to improve funnel health and conversions.
• Working in a remote-first, fast-moving SaaS environment.

Align With What We Value

At Endear, we live by five core principles. Here’s how they translate into this role:

• Customer First: Keeps the customer experience at the heart of every sales decision. Builds trust through authenticity and understanding of merchant pain points.
• Take Ownership: Treats the team’s goals as their own. Drives accountability, consistency, and pride in performance.
• Enable Autonomy: Equips the team with tools, clarity, and confidence to execute independently. Builds leaders, not dependencies.
• Under Promise, Over Deliver: Sets realistic expectations for pipeline and forecasting—and delivers with reliability and precision.
• Innovate & Deliver Value Quickly: Continuously refines systems, playbooks, and processes that drive measurable improvement.

About the Team

You’ll partner with:

• Casey Drake (Head of Sales): Transitioning to new product development—providing historical context and ongoing collaboration.
• Matt (Marketing): Aligning marketing campaigns, lead flow, and brand positioning.
• Baku (Consulting Partner): Supporting forecasting, 1:1s, and process refinement during onboarding.
• Leigh Sevin (CEO): Reporting, strategy, and overall revenue alignment.
• Executive Team: Strategic input on forecasting and team scaling.

We’re a small, focused, and highly capable team. Everyone has high ownership and autonomy—your leadership will directly shape how Endear continues to grow.

Our Hiring Process

• Screening interview with recruiter
• Behavioral interview with Sales Leader
• Panel interview with key team members
• Take-home work product exercise
• Final interview with Co-Founders 
• Offer 🎉

Compensation & Benefits

• Base + Variable Compensation
• Fully remote team
• Comprehensive healthcare (medical, dental, vision)
• Co-working or home office stipend
• Flexible PTO and unlimited vacation
• Opportunity to shape a proven sales engine into a scalable, high-performing machine



Apply Even If You Don’t Check Every Box

If this role excites you but you’re unsure if you meet every requirement, reach out anyway. We care about skills, motivation, and how you think more than perfect resumes.