Deployment Strategist

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.

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.

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.

What you'll do

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

Run the onboarding process so every new practice can quickly and effectively implement the Lassie Agent in their practice

Hold regular business reviews with practice owners, intervene early on churn risk, and identify expansion opportunities

Build and refine the implementation, account management, and retention playbooks that future CS hires will run

Drive a structured feedback loop with product, sales, and marketing. Your learnings shape the product, and our go-to-market strategy

What we'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

Joining us

To start, you'll have a handful of conversations with our team and founders. If there is mutual excitement, we'll invite you to the office where you'll work on a small project and meet the team.