Forward Deployed AI Strategist

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, Dev Ops, 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!

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 work streams 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.

• 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 work streams; 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

• 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

• Codify transformation methodology: translate blueprint and execution patterns into reusable frameworks for the practice
• Mentor Agentic Architects on executive engagement, strategic framing and scoping

• 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,…