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:

- Lead onboarding and deployment. Understand each practice’s workflows, configure AI agents to meet its needs, and guide customers through kickoff, setup, and customer training.

- Deliver value quickly. Drive activation during the critical first eight weeks, improving onboarding time, launch rates, and time to full agent productivity.

- Own customer relationships end to end. Serve as the primary point of contact from kickoff through adoption and renewal. Monitor account health, answer questions, and train current staff as practices grow.

- Account Management: Own and manage a book of +250 SMB accounts spanning the full customer lifecycle, scaling with our path to thousands of customers

- Drive retention: Understand customer concerns, address the underlying challenges, manage cancellation requests.

- Build repeatable processes.



Improve onboarding and account management playbooks, establish cross-functional workflows, and automate recurring tasks.

- Turn customer insights into action. Build a structured feedback loop with Product, Sales, and Marketing, using what you learn from customers to shape product improvements and our go-to-market strategy.

What we're looking for:

- You put customers first. You take ownership of customer problems, follow through to resolution, and take pride in delivering an exceptional experience.

- You have early-stage startup experience. You’ve operated in a fast-moving environment, ideally working directly with founders. Building onboarding or customer success playbooks from scratch is a plus.

- You’re energized by people. You bring warmth, enthusiasm, and curiosity to conversations and enjoy building lasting customer relationships.

- You learn quickly. You can get up to speed on new products and workflows and become a trusted resource for small business owners.

- You communicate value clearly. You connect product capabilities to business outcomes, navigate objections, and guide customers through change with patience and confidence.

- You use AI in your daily work. You already use AI tools to build, automate, and solve problems, and you’re comfortable troubleshooting how AI agents work in practice.

Location: This is an in-person role, 5 days a week in our San Francisco or downtown Toronto office. We value the connection, collaboration, and shared learning that come from working together.

Compensation and Benefits

- Compensation: $170,000 - $210,000 on-target earnings (OTE) on a 80/20 split plus a generous pre-IPO equity package.

- Individual offers will reflect your experience, relevant skills, and the scope of the role.

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.

📌 Deployment Strategist (Toronto)
🏢 Lassie
📍 Toronto