AI Deployment Strategist

About Cassidy

At Cassidy, we’re building software that helps teams move faster by automating complex, high-leverage workflows with AI. Our platform enables teams to deploy AI agents and automations inside business-critical processes — not just to eliminate busywork, but to handle real operational workflows across the tools they already use.

The Role

Deployment Strategists make sure customers get real, measurable value from Cassidy. The role combines consulting, product thinking, and account ownership. You'll help customers find the right problems to solve, turn those problems into clear requirements, and lead the work through rollout, adoption, and expansion.

You'll work directly with executives and with the teams doing the work every day. You'll run discovery, assess business value, set priorities, and define what success looks like. Working alongside our Solutions & Engineering team, you'll turn those decisions into production workflows and AI agents. You own business requirements, prioritization, adoption, and the customer relationship. Your Solutions & Engineering counterpart owns technical design and build.

Success means customers rely on what we deploy, can measure how it improves their business, and keep expanding what they run on Cassidy.

This role is based in New York City and requires working from our office. We value in-person collaboration, and we expect Deployment Strategists to be on site working closely with the broader go-to-market team.

What You'll Do

• Understand how the customer works. Interview teams, map processes, and find where work gets delayed or depends on unnecessary manual effort.
• Decide what's worth building. Assess automation opportunities, estimate their business value, and build a prioritized roadmap that shows customers where to start.
• Define the work. Turn discovery into requirements, priorities, and acceptance criteria that an engineer can act on. Keep scope grounded in the customer's needs as you learn more.
• Deliver with Solutions & Engineering. Partner with the Solutions & Engineering team through recurring build cycles. You'll resolve product questions, test with users, and coordinate feedback. Build prototypes and simple automations in Cassidy yourself to test ideas and clarify requirements.
• Own adoption. Plan rollouts, train users, develop internal champions, and track usage and business results after launch.
• Own the relationship. Serve as the primary point of contact for a portfolio of customers from onboarding through renewal. Run executive conversations and explain tradeoffs. Raise problems early, and give a clear recommendation when a customer's proposed approach needs to change.
• Grow the account. Monitor customer health and outcomes to manage risk before it escalates. Find new teams and workflows where Cassidy can help to drive renewal and expansions
• Close the loop with Product. Turn customer feedback into clear, actionable insights for the Product team.
• Share what works. Turn lessons from each deployment into playbooks, templates, and best practices the team can reuse as we scale.

Examples of the Work

• For a commercial insurance broker, you might run a discovery sprint on pre-sales processes (e.g., census generations). You'd identify the highest-return workflows, present a roadmap, and deliver the first few with Solutions & Engineering.
• For an existing customer, you might run a monthly review of usage and results. From there you'd identify two new departments ready to adopt Cassidy and scope their first workflows.

What We're Looking For

• 2-6 years of experience in Management or Technology Consulting, Customer Success, Account Management or a related customer-facing role
• You've changed how a team works. You can explain what you changed, why you made those decisions, and what happened.
• You can turn an unclear business problem into requirements, priorities, and a practical delivery plan.
• You ask good questions and follow up when an answer is vague. You're comfortable learning a business from both its leaders and its frontline teams.
• You're organized enough to manage multiple accounts and workstreams at once.
• Excellent communication skills — clear, direct, and confident with both technical and non-technical stakeholders
• You take ownership of outcomes, move work forward without detailed instructions, and respond thoughtfully to feedback.
• Comfort working with technical products (APIs, integrations, automation platforms, or AI-powered tools)
• Strong organizational skills and the ability to manage multiple accounts and priorities
• A collaborative mindset and comfort working closely with Sales, Product, and Engineering
• Bias toward ownership and problem-solving in fast-moving environments

Why Cassidy

• Work on a product customers rely on for business-critical workflows
• High-impact role with visibility across the company
• Competitive compensation, equity, and benefits
• A fast-growing, in-person NYC team that values clarity and execution
• Real ownership and the chance to help define how Customer Success works as we scale