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Salary: USD 175,000 - 215,000 / annual
Endear is building the first modern CRM for retail teams, empowering sales associates with AI-powered tools to drive customer relationships and revenue. The company works with brands like Reformation and Gorjana to transform in-store experiences.
As Director of Business Operations, you will own the systems connecting signed contracts through implementation, billing, and handoff to Customer Success. This is a hands-on, player-coach role reporting to the CEO. You'll inherit current processes, identify friction and operational risk, recommend improvements, and drive them to completion.
Key responsibilities include:
- Learning and mapping the customer journey from contract signature through implementation, billing, and CS handoff; prioritizing problems and improvements for CEO approval
- Owning legal and contracting workflows: reviewing, approving, documenting agreements, and translating terms into clear customer commitments
- Understanding and improving billing and plans systems, including setup, invoicing, and exception resolution
- Leading and developing the live-chat Customer Experience team, strengthening service quality, performance visibility, and CS coordination
- Managing contractors and agencies end-to-end: scope, selection, coordination, delivery, and budget accountability
- Establishing clear workflows and reliable follow-through across Sales, Product, Engineering, CX, billing, and CS
- Using AI thoughtfully to improve efficiency and provide leadership with visibility into contract terms, pricing, onboarding effort, support costs, billing, sales margin, and revenue quality
In your first six months, you'll map current systems, take ownership of legal/contracting, improve billing operations, lead the CX team, manage external resources, and establish cross-functional workflows. In year one, you'll build a dependable operations foundation, develop the CX team and partnerships, embed improved processes with documentation and controls, provide leadership with revenue quality and margin visibility, and create repeatable cross-functional ways of working.
You'll partner closely with the CEO and executive team, the Customer Experience team (which you'll lead), Customer Success (separate function with improved handoffs), Sales and the CRM owner, and Product & Engineering.
REQUIREMENTS:
- Experience in Business Operations, Strategy & Operations, Customer Operations, or adjacent role at Series A or similarly early-stage venture-backed startup
- Track record of inheriting operating systems, identifying improvement needs, and implementing changes that strengthen business operations
- Hands-on experience improving legal/contract operations and billing operations, with judgment to connect contract terms to implementation and billing requirements
- Experience managing a live-chat, customer experience, or comparable frontline service team, including distributed teammates and day-to-day performance management
- Experience improving cross-functional workflows from customer commitment through delivery, billing, and ongoing service, with clear handoffs to separate CS teams
- Experience owning contractors, agencies, or outside resources end-to-end: setting scope, managing delivery, recognizing 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 not required)
- Practical AI fluency: using AI tools in work and explaining where they improve operating workflows with appropriate review and accountability
- Strong execution and judgment: balancing details with broader business need, surfacing problems proactively, recommending paths, and delivering within agreed priorities and budget
