General Manager, Sunset Operations

About Sunset At Sunset, we’ve helped hundreds of venture-backed startups get through the end-to-end dissolution process, handling the legal, tax, and operational challenges that come with it. Over the past 3 years, Sunset has become one of the prominent providers of wind-downs in the startup community, with over 65% of our deals referred inbound from VCs, lawyers, and founders. The next challenge is to drastically scale delivery while maintaining and improving the customer experience. The Role As GM, Sunset Operations, you’ll own turning an operationally complex legal, tax, customer success, and support process into a scalable, repeatable, tech-driven service. You’ll lead the operating system for wind-down delivery, including team structure, capacity, AI-driven workflows, quality controls, and escalations. Your goal is to help us serve thousands of founders a year across industries and entity types without losing the care and judgment each case requires. You’ll be accountable for service quality, throughput, unit economics — and you’ll work closely with product, engineering, marketing, partnerships, and sales to improve the full customer journey. This is a hands-on operating leadership role. What You'll Do End-to-end delivery: Own the client journey from handoff and onboarding through legal and tax work, customer communication, support, and completion. Scale: Design an operating model that serves thousands of clients a year across new markets, industries, and entity types without growing headcount at the same rate. AI and automation: Partner with product and engineering to turn repeatable delivery work into AI-driven workflows. Team leadership: Build and lead customer success, support, legal, and tax teams with clear roles, training, quality standards, and escalation paths. Cross-functional partnership: Work with sales and marketing to improve handoffs and client expectations, and bring lessons from delivery back into the broader company. Performance: Own speed, quality, client experience, capacity, and cost to serve. How You'll Be Measured Client experience: NPS, CSAT, and performance against service-level agreements (SLAs). Unit economics: cost to serve, human hours per wind-down, and contribution margin per client. Automation: tickets deflected, tickets resolved by agents versus humans, and manual steps replaced by automation and AI. Speed and scale: time to complete a wind-down and total clients served each year. Breadth: new entity types and industries supported, while maintaining service quality and unit economics across them. Required aptitude Exceptional operator: You can turn complex, high-stakes work into reliable processes and know when a case needs individual judgment. Data-literate: You use service metrics and unit economics to spot problems, test changes, and see whether they worked. Systems builder: You can redesign workflows and put AI and automation to work yourself, with clear standards for quality and human review. Owner: You take responsibility for outcomes, from client experience to unit economics. Experience as a founder, head of operations, or GM is especially valuable. Cross-functional leader: You’ve improved how teams work together across operations, product, engineering, sales, and marketing, even when those teams did not report to you. People leader: You can hire, develop, and lead specialists and managers as the operation scales. Team: You’re excited to work in person, five days a week, from our Dumbo office. Compensation & Benefits 200K-350K base salary Meaningful equity 100% covered medical, dental, and vision Unlimited PTO Free gym + workout class memberships (via Wellhub) $500 desk allowance Up to $15,000 relocation bonus where applicable How We Hire Intro Chat (20 min): mutual fit and interests Operations Deep Dive (1 hr): walk through a complex service you built or scaled Take home: A short project designed to see how you think and work Onsite (3 hrs): discuss your approach, meet the team, and have snacks References -> Offer