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. We value craft, intellectual rigor, and direct communication. first Deployment Strategists, 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.

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

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 recent staff as practices grow. 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. Understand customer concerns, address the underlying challenges, manage cancellation requests. 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. Building onboarding or customer success playbooks from scratch is a plus.

You bring warmth, enthusiasm, and curiosity to conversations and enjoy building lasting customer relationships. You connect product capabilities to business outcomes, navigate objections, and guide customers through change with patience and confidence. in our San Francisco office or Toronto Office. 170,000 - $210,000 USD plus a generous pre-IPO equity package. 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 - Intel (Winnipeg)
🏢 Lassie
📍 Winnipeg