Forward Deployed AI Lead

Caylent

4d•$210,000 - $232,500•Remote

About The Position

Caylent's Anthropic Business Unit is a dedicated AI services practice built in partnership with Anthropic. The Forward Deployed AI Lead is the strategic and architectural lead on AI engagements. Paired with a Forward Deployed Engineer (FDE) who handles hands-on implementation, you own the engagement arc: shaping AI strategy, designing operating models, mapping AI outcomes to business value, and guiding executive stakeholders through adoption. You lead the room — the FDE builds what you architect. This is a cross-functional role. You engage across lines of business, not just engineering, connecting AI initiatives to the outcomes that matter to each part of the organization. Every engagement is anchored to Anthropic’s platform and focused on real AI adoption outcomes. Your clients span PE portfolio companies, growth-stage software businesses, and enterprise organizations. You are the strategic face of Caylent from kickoff through handoff.

Requirements

8+ years of software development or technical architecture experience across varied stacks, including hyperscaler environments
3+ years in engineering leadership, technical consulting, solutions architecture, or a combination
Demonstrated ability to engage across lines of business. You can talk to a VP of Engineering about CI/CD and a COO about operational efficiency in the same week
Experience designing or advising on AI operating models, technology adoption strategies, or digital transformation programs
Hands-on familiarity with Claude Code or equivalent AI-assisted development tools — you don’t need to configure them daily, but you need to speak the language credibly and direct an FDE’s work
Certified Claude Architect
Experience running structured stakeholder interviews, discovery sessions, and facilitated workshops with both technical and business audiences
Strong executive communication: writing and presenting to CTOs, VPs of Engineering, and line-of-business leaders
Experience delivering professional services engagements, including scope management, deliverable ownership, and client advisory
Working knowledge of CI/CD pipelines, DevOps practices, and modern software development workflows

Nice To Haves

Experience mapping AI initiatives to business outcomes (revenue, efficiency, risk, time-to-value) with executive-level ROI framing
Familiarity with PE portfolio company environments and board-level communication
Background in solutions architecture, platform engineering, or enterprise technology strategy
Experience with LLM prompt engineering, agentic AI workflow design, or AI product development
Direct experience with Claude Code’s extensibility model
Familiarity with SDLC maturity frameworks or workforce analytics (DORA, DevEx)
Experience designing and facilitating workshops for mixed audiences — engineers, product managers, and business stakeholders

Responsibilities

Own AI engagements end-to-end as the strategic lead, from discovery through executive handoff, partnered with an FDE who drives implementation
Run structured discovery across engineering, product, and business stakeholders to map organizational context, AI readiness, and strategic goals across lines of business
Design AI operating models that define how the organization adopts, governs, and scales AI. Not just within engineering, but across the business
Define AI outcome maps that tie initiatives to measurable business results: efficiency gains, revenue impact, risk reduction, and time-to-value
Lead AI maturity assessments and architect near-term and long-term adoption roadmaps aligned to Anthropic’s platform capabilities
Facilitate executive workshops and enablement sessions for audiences ranging from engineering teams to C-suite leaders
Deliver executive presentations to CTOs, VPs of Engineering, and line-of-business leaders covering current-state findings, ROI projections, and strategic recommendations
Direct FDE work on Claude Code tooling, prompt architecture, and workflow automation. You set the technical direction, the FDE executes
Identify expansion opportunities across lines of business. AI strategy work naturally surfaces adjacent needs in departments beyond the initial engagement
Shape follow-on scope throughout the engagement: by Week 1, you should have a working hypothesis for the next engagement; by the final on-site block, you present it
Build executive relationships that position Caylent as a long-term AI strategy partner, not a one-time vendor
Attend on-site for the final Catalyst block: readout, workshop, and executive presentation
Contribute reusable strategy frameworks, delivery artifacts, and methodology improvements back into the practice at engagement close
Lead AI strategy engagements spanning multiple teams, platforms, and business functions
Collaborate with FDEs to refine the architect-engineer delivery model and improve handoff patterns