Deployment Strategist

Lassie; Toronto; On-site; CAD 241,000 - 298,000; Full time

Job summary

Lassie is seeking a Deployment Strategist to guide hundreds of small businesses from signup to their first automated workflow. You will own customer health across an expanding book of accounts, configuring agents and leading teams through onboarding, change management, and renewal.

You will shape how customer success works at Lassie and develop playbooks for implementation, account management, and retention.

Qualifications

• Customer-first mindset with ownership of issues.
• Experience in early-stage startups, with founders.
• Strong communication and relationship-building skills.
• Fast learner who adapts to new products and workflows.
• Ability to articulate product value to customers and stakeholders.
• Proficient with AI tools to automate tasks and troubleshoot agents.

Responsibilities

• Lead onboarding and deployment. Understand each practice’s workflows, configure AI agents to meet its needs, and guide customers through kickoff, setup, and training.
• Deliver value quickly. Drive activation during the first eight weeks, improving onboarding time and time to full agent productivity.
• Build repeatable processes. Improve onboarding and account management playbooks and automate recurring tasks.
• Own customer relationships end to end. Serve as the primary contact from kickoff through adoption and renewal.
• Turn customer insights into action. Build a feedback loop with Product, Sales, and Marketing to shape improvements.
• Drive retention. Understand concerns and address cancellation requests.

Skills

Customer focus

Startup experience

People skills

Learn quickly

Value communication

AI tool usage

Tools

AI tools

Job description

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.

• Build repeatable processes. 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 new 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.

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

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 office or Toronto Office.

Compensation and Benefits

• Compensation: $170,000 - $210,000 USD 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.