Caylent is a cloud native services company that helps organizations bring the best out of their people and technology using Amazon Web Services (AWS). We provide a full-range of AWS services including workload migrations and modernization, cloud native application development, DevOps, data engineering, security and compliance, and everything in between. At Caylent, our people always come first. We are a global company and operate fully remote with employees in Canada, the United States, and Latin America. We celebrate the culture of each of our team members and foster a community of technological curiosity. Come talk to us to learn more about what it means to be a Caylien! About This Role Caylent's Anthropic Enablement & Engineering (AE2) practice is a dedicated AI services team built in partnership with Anthropic. We were Anthropic's first pure-play delivery partner, and are working closely with them to define the next evolution of Software Development. The Forward Deployed AI Strategist leads the work that defines what transformation looks like before a single Architect is deployed. You own blueprint engagements — comprehensive assessments of how an organization builds software across the full SDLC and PDLC, where AI can change the economics, and what a credible multi-phase roadmap looks like. You then lead the execution programs that follow, coordinating Agentic Architects across parallel workstreams and driving outcomes against the plan you set. On engagements where scope and timeline call for it, you step in part-time as an Agentic Architect. Your clients are PE portfolio companies, growth-stage software businesses, and enterprise engineering organizations where transformation decisions are made at the C-suite and board level. What You'll Do Lead AI transformation blueprint engagements: current-state assessment across SDLC and PDLC, gap analysis, and prioritized initiative roadmap Run executive discovery with CTOs, CPOs, and VP Engineering to surface strategic goals, constraints and success criteria Assess AI adoption posture across engineering and product functions — tooling, workflows, org design, delivery practices Define initiative sequencing: what to address first, what to automate, where to standardize Develop board‑ready transformation cases that connect AI investment to PE value creation metrics — revenue per head, time‑to‑feature, delivery predictability Facilitate executive alignment workshops that move stakeholders from awareness to decision Lead multi‑team AI transformation programs following blueprint delivery Coordinate Agentic Architects across parallel workstreams; translate roadmap priorities into sprint‑level milestones and delivery plans Own the executive‑sponsor relationship through delivery close Step into Agentic Architect responsibilities on engagements where hands‑on execution is required Business Development Shape follow‑on scope throughout blueprint delivery — by handoff you have a working hypothesis for the execution program Present the execution proposal at blueprint readout Surface expansion signals across the client organization and route them to the account team Internal Contribution Codify transformation methodology: translate blueprint and execution patterns into reusable frameworks for the practice Mentor Agentic Architects on executive engagement, strategic framing and scoping Who Thrives Here Thinks in roadmaps, not tasks. You see where an organization needs to be 12 months from now and can build a credible path to get there. Strategy that isn't accountable to outcomes is not strategy. Can still do the work. You use Claude for all of your work. You'll step into Agentic Architect engagements when the situation calls for it. Seniority here means broader scope, not distance from delivery. Credible at the board level. You've presented transformation cases to PE sponsors and C‑suites and know how to connect technical decisions to business value without hand‑wav­ing. Makes the methodology better. Every blueprint you run should make the next one faster. You feed patterns back into the practice rather than keeping them in your head. Multiplies Architects. You can set direction, coordinate execution and step back. You know what effective oversight looks like versus micromanagement. This is a poor fit for purely advisory profiles. You own outcomes, not just recommendations. Why This Team Ground floor of something real: this BU is early, well‑resourced and anchored to Anthropic. You're writing the playbook, not inheriting one. Define the methodology: you are shaping how AI transformation gets scoped and delivered at scale. The frameworks you build here will drive how this practice grows. Proximity to the PE channel: your clients are PE portcos and enterprise engineering orgs at the frontier of AI adoption where transformation decisions are being made now. Revenue upside: Strategists who drive account expansion earn on revenue generated, not just delivery margin. AI‑native by default: this team uses AI in how it works. Specification‑First Engineering is how we move from prototype to production fast. Outcomes, not hours: advancement tied to delivery performance and account growth, not utilization. Equitable Life – Hybrid Plan 100% Premium Coverage for the employee and dependents Long‑Term Disability Unlimited Vacations Paid Holidays Paid for exams and certifications Peer bonus awards State of the art laptop and tools Equipment & Office Stipend Annual stipend for Learning and Development Work with an amazing worldwide team and in an incredible corporate culture Base Salary Range: The expected base salary range for this position is CAD $215,000 – $235,000 per year, commensurate with experience and qualifications. Additional Compensation Components: In addition to the base salary, the compensation package may include bonuses, commissions, equity and other incentives. The specific components will vary depending on the role and individual and/or company performance. NOTE: We’re unable to provide visa sponsorship now or at any time in the future. We are proud to be an equal opportunity employer. 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