Head of Customer Success

About Cassi

At Cassi, we’re building the AI operating system for home operations — a single system that brings together everything required to run a home, including assets, documents, maintenance, service coordination, and operational history.

We’re starting with property managers responsible for owner-occupied homes, where operational complexity is high and fragmented systems are most painful. But this is just the entry point. Our goal is to create the standard platform that any homeowner or operator relies on to understand, maintain, and manage a home over its entire lifecycle.

Cassi replaces disconnected tools, inboxes, spreadsheets, and tribal knowledge with structured, searchable, and actionable home records that stay up to date as work happens. By reducing the cognitive and administrative burden of home operations, we enable our partners to operate more consistently today — while building the foundation for how homes are managed everywhere tomorrow.

We’re looking for an exceptional customer success leader who can be the face of Cassi to our partners. This isn’t a typical CS role – you’ll have the chance to help build customer success function from scratch by defining what white-glove service means and directly driving revenue through retention and expansion within our partner base.

You’ll own the entire post-sale customer experience from implementation and onboarding through continued relationship management, quarterly business reviews, renewals, and upsells. This gives you the chance to work directly with Cassi’s founding team and executives of luxury residential builders and top-tier service firms.

• 4+ years in customer success, customer support, or account management roles, including 2+ years in a leadership or player-coach role
• Revenue generator:
  Proven track record of driving strong logo retention and net revenue retention
• White-glove support:
  Demonstrated ability to lead world-class implementation and onboarding for high-touch and high-expectation partners
• Ability to build rapport:
  Exceptional interpersonal skills and ability to inspire trust with C-level executives
• Data-driven:
  Track record of making decisions backed by numbers and managing through KPIs
• Self-starter:
  History of taking initiative and not afraid to build processes from the ground up
• Wear many hats:
  We’re a seed-stage startup – the prospect of lending a hand across various departments and work streams is exciting to you
• Bias for Action:
  Comfortable moving fast, iterating, and self-correcting. We’re not afraid of failure, we’re afraid of slow pace

• Technical chops:
  Experience with APIs, integrations, and data structures to act as the liaison between our partners and the Cassi engineering team
• Prior experience as Solutions Engineer, Forward Deployed Engineer, or similar role

• Create and document a scalable implementation and onboarding playbook that can support our aggressive growth targets
• Create and lead an A+ Customer Success function
• Own partner onboardings with limited founder involvement
• Conduct Quarterly Business Reviews and take a data-driven approach to ensuring healthy partner relationships
• Trusted voice of Cassi for luxury partners
• Complete ad-hoc projects as needed

• Competitive compensation
• Equity in early-stage startup
• Full medical, dental, and vision coverage
• 401(k)
• Flexible PTO policy
• Opportunity to work on a high-performing, scrappy team that likes to have fun

Our office is in New York, NY near Penn Station. This is an in-office position, though we offer flexibility for occasional remote work when needed

Cassi is an equal opportunity employer and does not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Employment decisions are based solely on merit, qualifications, and business needs.