Forward Deployed AI Strategist

Caylent

5h•Remote

About The Position

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.

Requirements

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

Nice To Haves

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

Responsibilities

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
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