Startups · AI

Deployment Strategist

Lassie · San Francisco, CA · On-site

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About Lassie

Lassie automates your admin — enrollments, payment posting, EFT reconciliation — so your team can focus on patients. Backed by a16z.

About the role

As one of Lassie's first Deployment Strategists, you'll guide hundreds of small businesses from signup to their first automated workflow and ultimately to a business that runs itself with Lassie. You'll own customer health across a growing book of accounts: setting up agents, guiding owners through change management, minimizing churn, and preparing accounts for expansion.

What they're looking for

  • You're customer-obsessed: if a customer has a problem, you find a way to make it right and take pride in exceptional customer experience
  • You've operated at an early-stage startup, preferably working directly with founders. Bonus: you've built onboarding or CS playbooks from scratch
  • You thrive on human interaction. You bring high energy into every call and are energized by building and maintaining strong business relationships
  • You're a fast learner who can quickly become a trusted expert for the small business owners of America
  • You can sell value: communicate outcomes, handle objections, and guide people through change with patience and confidence
  • You already use AI tools daily to build and operate, and you're comfortable troubleshooting how AI agents work in practice
More about this role

Our mission is to help small businesses run themselves. We’re starting with doctors’ offices, building autonomous systems that handle busywork and complete the workflows that keep the office moving every day. Our team is small, flat, and ambitious. We value craft, intellectual rigor, and direct communication.

As one of Lassie's first Deployment Strategists, you'll guide hundreds of small businesses from signup to their first automated workflow and ultimately to a business that runs itself with Lassie. You'll own customer health across a growing book of accounts: setting up agents, guiding owners through change management, minimizing churn, and preparing accounts for expansion.

You'll also help define how customer success works at Lassie. You'll build the playbooks for implementation, account management, and retention, and set the bar for customer obsession that future hires will meet. You are the voice of the customer, internally working directly with product and the founders to make sure customer needs are heard, understood, and met with excellent solutions.

Own and manage a book of accounts spanning the full customer lifecycle, scaling with our path to thousands of customers

Run...

Read the full posting on Lassie's site ↗

Customer Success

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