Deployment Strategist: Onboard & Scale with AI Equity

Lassie

Toronto

On-site

CAD 241,000 - 298,000

Full time

14 days+

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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.