Forward Deployed AI Lead

This is a fully remote position, open to applicants in Canada.

📋 Description

• Lead AI initiatives comprehensively as the strategic authority, overseeing the process from initial discovery to executive handoff, collaborating with an FDE who manages implementation.

• Conduct organized discovery sessions with engineering, product, and business stakeholders.

• Create AI operating models that outline how organizations can adopt, govern, and scale AI across their operations.

• Develop AI outcome maps that connect initiatives to quantifiable business results.

• Oversee AI maturity evaluations and design adoption roadmaps that align with Anthropic’s platform capabilities.

• Conduct executive workshops and training sessions.

• Present findings to executives, including current-state analysis, ROI forecasts, and strategic advice.

• Supervise FDE efforts on Claude Code tools, prompt architecture, and workflow automation.

• Spot opportunities for expansion across different business lines.

• Shape subsequent scopes throughout engagements.

• Cultivate executive relationships to position Caylent as a long-term partner for AI strategy.

• Participate onsite during the final Catalyst block, which includes readouts, workshops, and executive presentations.

• Contribute to reusable strategy frameworks, delivery artifacts, and improvements in methodology.

• Lead AI strategy projects that involve multiple teams, platforms, and business functions.

• Collaborate with FDEs to enhance the architect-engineer delivery model and handoff processes.

⛳️ Requirements

• 8+ years of experience in software development or technical architecture across diverse stacks, including hyperscaler environments.

• 3+ years in engineering leadership, technical consulting, solutions architecture, or a combination thereof.

• Proven track record of engaging across various business lines.

• Experience in designing or providing advice on AI operating models, technology adoption strategies, or digital transformation initiatives.

• Practical knowledge of Claude Code or similar AI-assisted development tools.

• Certified Claude Architect.

• Experience conducting structured stakeholder interviews, discovery meetings, and facilitating workshops with both technical and business audiences.

• Excellent executive communication skills, including the ability to write and present to CTOs, VPs of Engineering, and line-of-business leaders.

• Experience in delivering professional services engagements, which includes scope management, ownership of deliverables, and client advisory roles.

• Proficient understanding of CI/CD pipelines, DevOps practices, and contemporary software development workflows.

• Must have current legal authorization to work in the country where the position is located; Caylent is unable to sponsor visa or work permit applications.

• Preferred: Experience correlating AI initiatives to business outcomes with executive-level ROI considerations.

• Preferred: Familiarity with environments related to PE portfolio companies and board-level communication.

• Preferred: Background in solutions architecture, platform engineering, or enterprise technology strategy.

• Preferred: Experience with LLM prompt engineering, agentic AI workflow design, or AI product development.

• Preferred: Direct experience with the extensibility model of Claude Code.

• Preferred: Knowledge of SDLC maturity frameworks or workforce analytics (DORA, DevEx).

• Preferred: Experience in designing and facilitating workshops for diverse audiences.

🏝️ Benefits

• 100% remote work.

• Equitable Life - Hybrid Plan.

• 100% Premium Coverage for the employee and dependents.

• Competitive phantom equity.

• Long-Term Disability.

• 4% Pension match (employer contribution).

• Unlimited Vacations.

• Sick Leave.

• Paid Holidays.

• Parental Leave.

• Coverage for exams and certifications.

• Peer bonus awards.

• State-of-the-art laptop and tools.

• Equipment & Office Stipend.

• Individual professional development plan.

• Annual stipend for Learning and Development.

• Opportunity to work with an outstanding global team in an exceptional corporate culture.

• May require up to 50% travel, depending on business needs.