Forward Deployed AI Strategist

Responsibilities

• Transformation Strategy
• 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
• Execution Leadership
• 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

Requirements

• Required
• Significant experience across 12+ years across software development, technical consulting, or a combination, with demonstrable knowledge / experience on both SDLC and PDLC sides of a software organization
• Proven success 5+ years leading transformation, strategy, or technical advisory engagements with engineering and product organizations
• Hands-on experience with Claude Code or equivalent AI-assisted development tools in a real workflow
• Experience building and presenting technology transformation roadmaps to C-level and board audiences
• Strong working knowledge of modern SDLC (CI/CD, DevOps, cloud-native) and product development (agile delivery, roadmapping, product operations)
• Experience sizing and sequencing multi-team, multi-quarter transformation programs
• Prior professional services delivery experience with scope ownership and deliverable accountability
• Preferred
• Certified Claude Architect
• Background in PE or growth-equity-backed software companies - understand value creation timelines and board expectations
• Experience leading programs that span engineering and product simultaneously
• Familiarity with developer experience and delivery metrics frameworks (DORA, DevEx, SPACE)
• Experience designing AI governance and adoption guardrails for enterprise organizations
• Direct experience building or operating agentic AI systems in production
• 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 ge

Benefits

Additional Information

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.

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