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 helping brands like Reformation, Gorjana, and many more, turn real customer relationships into growth powered by intuitive software and thoughtful design. As Endear grows, we’re building the operating foundation to scale. We’re looking for a hands-on Business Operations leader to take ownership of the systems behind our customer journey, improve how work moves across teams, and surface the next operational problems we should solve.
Position Overview The Director, Business Operations will inherit and improve the systems that connect signed contracts to implementation, billing, and the handoff to Customer Success. You’ll own high-impact work across legal and contracts, billing operations, Customer Experience, and the cross-functional processes that help Endear serve customers well. This is a hands-on Director-level player-coach role. You’ll learn how current processes work, identify friction and risk, recommend practical improvements, and drive them through to results. You’ll bring priorities and tradeoffs to Leigh, Endear’s CEO, for approval while owning the plan, coordination, and follow-through within agreed direction and budget. You’ll lead the Customer Experience (CX) live-chat team and own operational workflows across contracts, implementation, and billing. Customer Success (CS), including onboarding and account management, remains a separate function; you’ll improve the handoffs with that team. This is not a HubSpot or CRM administrator role, and it is not a sales-only Revenue Operations role. You’ll work with the existing CRM owner, manage contractors or agencies end to end, and know when a problem calls for engineering or other technical help. Visibility into sales margin and revenue quality will support better decisions, alongside the broader operating work.
What You’ll Accomplish In your first 6 months, you’ll…
- Learn the current systems and map the customer path from signed agreement and Schedule A through implementation, billing, and the handoff to Customer Success; bring Leigh a prioritized set of problems and recommended improvements.
- Take ownership of the legal and contracting workflow, improving how agreements are reviewed, approved, documented, and translated into clear customer commitments.
- Understand and improve the billing and plans system, including the operating processes that support accurate setup, invoicing, and resolution of exceptions.
- Lead and develop the live-chat Customer Experience team, strengthening service quality, team ownership, performance visibility, and coordination with Customer Success.
- Own contractor and agency work from scope and selection through coordination, delivery, and follow-up; manage spend within agreed budgets and raise needs for approval.
- Establish practical workflows, clear owners, and reliable follow-through across Sales, Product, Engineering, CX, billing, and CS handoffs.
- Use AI thoughtfully and build visibility across functions to improve the overall efficiency and performance of the org, including tracking contract terms, pricing, onboarding effort, support costs, billing, sales margin, and revenue quality.
In your first year, you’ll…
- Build a dependable Business Operations foundation for the full customer journey, with clear ownership from contract signature through implementation and billing to the Customer Success handoff.
- Develop the CX live-chat team and operational partnerships; identify which sort of resources (agency, contractor, FTE)can improve outcomes and make clear recommendations about investment.
- Embed improved contracting and billing processes with useful documentation, controls, and clear escalation paths that reduce executive follow-up and customer friction.
- Give leadership timely, decision-ready visibility into revenue quality and sales margin, connecting commercial terms and service costs to operational choices, while continuing to improve and grow the customer support/CX team by evolving from purely inbound to more outbound and proactive support.
- Create repeatable cross-functional ways of working with Sales, Product, Engineering, CX, and CS while keeping responsibilities clear across teams.
- Expand your ownership as Endear grows by spotting the next operational constraint, proposing a practical solution, and delivering results within the direction and budget approved by Leigh.
You’ll Thrive in This Role If… You Have Experience With
- Experience in Business Operations, Strategy & Operations, Customer Operations, or a broad adjacent role at a Series A company or a similarly early-stage, venture-backed startup.
- A record of inheriting operating systems, finding what needs to improve, and implementing changes that make the business work better.
- Hands-on experience improving legal or contract operations and billing operations, including the judgment to connect contract terms with implementation and billing requirements.
- Experience managing a live-chat, customer experience, or comparable frontline service team, including distributed teammates and day-to-day performance.
- Experience improving cross-functional workflows from a customer commitment through delivery, billing, and ongoing service, with clear handoffs to a separate Customer Success team.
- Experience owning contractors, agencies, or other outside resources end to end; can set scope, manage delivery, and recognize when to bring in technical expertise.
- Comfort using operational data to understand revenue quality and sales margin; exposure to tools such as Fin, HubSpot, Stripe, and Shopify. Deep HubSpot administration is not required.
- Practical AI fluency: you use AI tools in your work and can explain where they improve an operating workflow, with appropriate review and accountability.
- Strong execution and judgment: you balance the details with the broader business need, surface problems proactively, recommend a path, and deliver within agreed priorities and budget.
Align With What We Value At Endear, we live by five core principles. Here’s how they translate into what we’re looking for in this role:
Customer First:
Connects operational choices to merchants’ and sales associates’ experience. Builds reliable contracting, implementation, billing, and live-chat support practices, with smooth handoffs to Customer Success.
Take Ownership:
Takes responsibility for outcomes, not just assigned tasks. Learns how a system works, identifies what should change, brings a clear recommendation to Leigh, and drives the approved improvement through completion.
Enable Autonomy:
Creates clear workflows, documentation, and ownership so CX, Sales, Product, Engineering, and Customer Success can do their work with confidence while keeping CRM ownership with its designated team.
Under Promise, Over Deliver:
Communicates priorities, risks, tradeoffs, and timing early. Makes thoughtful recommendations about contractor, agency, and technical resources, then follows through on approved plans.
Innovate & Deliver Value Quickly:
Acts quickly on meaningful operational improvements, using systems and AI where they help. Measures whether changes improve customer experience, revenue quality, or team execution. About the Team
You’ll partner most closely with:
- Leigh and the Executive Team: Bring forward operational problems and recommendations, seek approval on priorities and spend, and own execution and results within the agreed direction.
- Customer Experience: Lead the live-chat team and improve its workflows, service quality, and operating model.
- Customer Success: Partner on the handoff from implementation and billing into onboarding and account management; CS remains a separate function.
- Sales and the CRM owner: Improve the operational path from commercial commitments to customer launch and accurate billing, coordinating with the existing HubSpot/CRM owner as needed.
- Product & Engineering: Explain operational problems clearly, bring in technical resources when useful, and coordinate practical improvements to internal systems and workflows.
We’re a small team with big ambitions - collaborative, customer-obsessed, and deeply excited about helping retail teams build better customer relationships.
Our Hiring Process
- Recruiter Screen
- Behavioral Interview with Hiring Manager & Co-Founder
- Work Product / Operational Case Study
- Panel Interview with key cross-functional team members
- Final Conversation with Co-Founder + Executive Team
- Offer 🎉
Compensation & Benefits
- Base Salary: $175–215K
- Equity Eligible
- Fully remote team
- Comprehensive healthcare: medical, dental, and vision
- Co-working or home-office stipend
- Flexible PTO and unlimited vacation
- Opportunity to build the operating foundation for a fast-growing, category-defining company
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.