Director, Business Operations

Endear • ,

7d • $175,000 - $215,000 • Remote

About The Position

Endear is hiring a hands-on Director, Business Operations to build and improve the operating foundation behind its customer journey. The role owns workflows connecting signed contracts to implementation, billing, and the handoff to Customer Success, with work spanning legal and contracts, billing operations, Customer Experience, and cross-functional processes. This is a Director-level player-coach position: the successful candidate will learn existing processes, identify friction and risk, recommend practical improvements, and drive approved changes through to results. Priorities and tradeoffs are brought to Leigh, Endear’s CEO, for approval; the Director owns planning, coordination, and execution within the agreed direction and budget.

The Director will lead the Customer Experience live-chat team and own operational workflows across contracts, implementation, and billing. Customer Success, including onboarding and account management, remains a separate function, and the Director will improve handoffs with that team. The position is not a HubSpot or CRM administrator role and is not a sales-only Revenue Operations role. The Director will collaborate with the existing CRM owner, manage contractors or agencies end to end, and identify when engineering or other technical support is appropriate. Operational visibility into sales margin and revenue quality will inform decisions alongside the broader business operations work.

During the first six months, the Director will map the customer path from signed agreement and Schedule A through implementation, billing, and the Customer Success handoff; prioritize operational problems and recommend improvements; take ownership of legal and contracting workflows; improve billing and plans processes; develop the live-chat CX team; manage outside resources and budgets; and establish clear cross-functional workflows and ownership. The role will also use AI thoughtfully and improve visibility into contract terms, pricing, onboarding effort, support costs, billing, sales margin, and revenue quality.

Within the first year, the Director will establish dependable ownership across the customer journey, embed improved contracting and billing processes with documentation and controls, provide leadership with decision-ready revenue-quality and sales-margin information, and develop CX operations toward more outbound and proactive support. The role will create repeatable ways of working across Sales, Product, Engineering, CX, and CS, and expand its ownership as the company grows by identifying and solving emerging operational constraints.

The role partners closely with Leigh and the Executive Team, Customer Experience, Customer Success, Sales and the CRM owner, and Product & Engineering. Endear describes itself as a small, collaborative, customer-focused team working to help retail teams build better customer relationships.

Requirements

• Experience in Business Operations, Strategy & Operations, Customer Operations, or a broad adjacent role at a Series A company or similarly early-stage, venture-backed startup.
• A record of inheriting operating systems, identifying areas for improvement, and implementing changes that improve business operations.
• Hands-on experience improving legal or contract operations and billing operations, including connecting 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 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, including scoping and delivery management, and recognizing when technical expertise is needed.
• Comfort using operational data to understand revenue quality and sales margin.
• Practical AI fluency, including use of AI tools in work and the ability to explain where they improve workflows with appropriate review and accountability.
• Strong execution and judgment, including balancing details with broader business needs, surfacing problems proactively, recommending a path, and delivering within agreed priorities and budget.

Nice To Haves

• Exposure to tools such as Fin, HubSpot, Stripe, and Shopify.

Responsibilities

• Map and improve the customer journey from signed agreement and Schedule A through implementation and billing to the Customer Success handoff.
• Identify operational friction and risk, prioritize problems, recommend practical improvements, and execute approved plans within agreed direction and budget.
• Own and improve legal and contracting workflows, including agreement review, approval, documentation, and translating terms into customer commitments.
• Improve billing and plans operations, including accurate setup, invoicing, and exception resolution.
• Lead and develop the Customer Experience live-chat team, improving service quality, ownership, performance visibility, and coordination with Customer Success.
• Manage contractors, agencies, and other outside resources from scoping and selection through coordination, delivery, and follow-up; manage spending within approved budgets and seek approval for additional needs.
• Establish clear workflows, ownership, and follow-through across Sales, Product, Engineering, CX, billing, and Customer Success handoffs.
• Use AI thoughtfully and improve operational visibility into contract terms, pricing, onboarding effort, support costs, billing, sales margin, and revenue quality.
• Develop a Business Operations foundation with clear ownership, documentation, controls, and escalation paths that reduce customer friction and executive follow-up.
• Provide leadership with timely, decision-ready visibility into revenue quality and sales margin, connecting commercial terms and service costs to operational decisions.
• Recommend appropriate agency, contractor, or employee resources to improve CX outcomes, and evolve support from primarily inbound to more outbound and proactive service.
• Partner with the existing CRM owner and coordinate with technical teams when technical expertise or system improvements are needed.

Benefits

• Base salary of $175,000–$215,000.
• Equity eligible.
• Fully remote team.
• Comprehensive medical, dental, and vision healthcare.
• Co-working or home-office stipend.
• Flexible PTO and unlimited vacation.
• Opportunity to build the operating foundation for a fast-growing, category-defining company.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed