Forward Deployed AI Lead

Responsibilities

• Strategy and Architecture
• 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
• Client Relationship and Business Development
• 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
• Internal Contribution
• 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

Requirements

• Required
• 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 m

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 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.

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