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Open nowPosted 74 days ago

Forward Deployment Strategist (Canada)

Workable (global search)108,016 open roles

Where
Toronto, ON, Canada
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Your applicationOpen nowForward Deployment Strategist (Canada)Workable (global search) · Toronto, ON, Canada

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7.9% of postings close within 7 days. Measured by our own scanner across the market. Workable (global search) postings stay open a median of 7 days.

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  2. 3.6%3 days
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  4. 14.9%14 days
  5. 34.0%30 days
This job: posted 74 days ago

Workable (global search) median: 7 days open

The posting

Rockstar is recruiting for the agentic AI platform for enterprise accounting. The company's three co-founders scaled finance at a major data security company from $5M ARR to a $15B NYSE IPO, built the reconciliation and billing systems behind a leading streaming company's $32B in annual revenue, and built AI infrastructure serving two billion monthly users at a major social media company. They have raised $41M from Redpoint Ventures, Kleiner Perkins, and Audacious Ventures, and have processed more than $400B across 350M transactions at 100.00% accuracy for customers including Scale AI, Rippling, Glean, Zendesk, Handshake, Zip, and Decagon.

Location: Toronto (On-site) Employment Type: Full time Department: Engineering & Product

About the Client

The client is the agentic AI platform for enterprise accounting. Its agents do the accounting work itself — journal entries, transaction matching, reconciliations, and flux analysis — continuously and with a full audit trail. Accountants review and approve, and nothing posts without a person signing off; the client removes the grind, not the human.

The client's three co-founders scaled finance at a major data security company from $5M ARR to a $15B NYSE IPO, built the reconciliation and billing systems behind a leading streaming company's $32B in annual revenue, and built AI infrastructure serving two billion monthly users at a major social media company.

The client has raised $41M from Redpoint Ventures, Kleiner Perkins, and Audacious Ventures, joined by former industry executives and finance leaders from well-known tech companies. To date, the client has processed more than $400B across 350M transactions at 100.00% accuracy, for customers including Scale AI, Rippling, Glean, Zendesk, Handshake, Zip, and Decagon.

The Role

Deployment is where the client proves itself. The client is looking for a Forward Deployment Strategist to guide enterprise customers through complex implementations and make sure they get measurable results, working directly with CFOs, controllers, and accounting operations teams to deploy the platform, automate their close, and deliver efficiency gains they can point to.

The role is cross-functional by nature. The Forward Deployment Strategist will work daily with Engineering, Product, Sales, and Customer Success, shape the deployment methodology itself, lead implementations, and be the bridge between what customers need and what the product does. Success looks like faster deployments, stronger adoption, and field insight turned into repeatable playbooks.

What the Forward Deployment Strategist Will Do

  • Own technical and operational delivery for multiple enterprise implementations, so each customer reaches its automation and close-efficiency goals
  • Act as the primary interface between customers, Product, and Engineering, translating accounting workflows into well-defined implementation plans
  • Manage deployment timelines, dependencies, and milestones, removing blockers and coordinating technical resources
  • Create standardized frameworks, tools, and templates for deploying the client's platform across customers and industries
  • Support pre-sales scoping and discovery to define requirements, feasibility, and implementation plans for enterprise prospects
  • Bring field insight into roadmap priorities, capacity planning, and future platform capabilities
  • Identify patterns across deployments, capture best practices, and improve delivery velocity and customer outcomes

What the Client Is Looking For

  • 3 or more years in enterprise customer-facing technical roles such as solutions engineering, forward deployed engineering, or technical implementation
  • A track record of leading complex, high-stakes software deployments at large enterprises
  • Strong understanding of financial systems such as NetSuite, SAP, Oracle, or Workday, or experience working in or with finance operations teams
  • Ability to translate between technical and non-technical audiences, guiding engineers and finance stakeholders toward a common solution
  • Excellent project management, communication, and problem-solving skills
  • Experience designing scalable processes and standardizing workflows
  • Comfortable in a fast-paced, ambiguous environment with a high degree of ownership
  • Curiosity about AI and what it can do for enterprise operations

Why Join

  • Team and culture: The client is early and moving fast. The playbook here gets written, not inherited, and the person closest to the work makes the call. The client looks for people who build from first principles and hold themselves accountable for what actually lands — people who'd rather build the category than join it.
  • The work: Agentic accounting is a category being defined right now, and the client is one of the companies defining it. The product does the accounting work itself, so what the Forward Deployment Strategist builds, sells, or deploys shows up in a customer's books.
  • The people: Founders who ran finance orgs at major tech companies and built the close systems at top streaming and social platforms. Engineers from well-known tech companies. Controllers and accountants on the team who have closed books themselves. Small teams in San Mateo and Toronto that work in the same room, say what they think, and hold a high bar.
  • The process: A person reads every application, and candidates are told where they stand at every stage.

A Note on AI

The client builds AI and expects candidates to use it. Candidates are encouraged to use AI to research the client and to prepare. In live conversations, the client wants candidates' own thinking in their own words, and if a candidate uses AI on a take-home exercise, they should note where it helped.

Benefits

  • Competitive salary
  • 401(k) for U.S. employees
  • Unlimited PTO
  • Lunch in the office
  • Commuter benefits
  • In-office schedule: four to five days a week in the client's downtown Toronto office, near Union Station

Equal Opportunity

The client is an equal opportunity employer and does not discriminate on the basis of race, color, ethnicity, ancestry, national origin, religion, sex, gender, gender identity, gender expression, sexual orientation, age, disability, veteran status, genetic information, marital status, or any other legally protected status. Candidates who need an accommodation at any point in the process are encouraged to let the client know so it can be arranged.

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