Forward Deployed AI Lead

Role

The Forward Deployed AI Lead is the strategic and architectural lead on AI engagements within Caylent’s Anthropic Business Unit. Paired with a Forward Deployed Engineer (FDE) who implements solutions, you own the engagement arc—from discovery, through executive enablement, to handoff—designing AI operating models and mapping initiatives to measurable business outcomes.

Key Responsibilities

Strategy & Architecture

• Own AI engagements end-to-end as the strategic lead, partnered with an FDE who drives implementation
• Run structured discovery across engineering, product, and business stakeholders to assess AI readiness and strategic goals
• Design AI operating models for adoption, governance, and scaling across business functions
• Define AI outcome maps tying initiatives to measurable results (efficiency, revenue, risk reduction, time-to-value)
• Lead AI maturity assessments and architect adoption roadmaps aligned to Anthropic’s platform
• Facilitate executive workshops and deliver presentations to CTOs, VPs of Engineering, and line-of-business leaders
• Direct FDE work on Claude Code tooling, prompt architecture, and workflow automation

Client Relationship & Business Development

• Identify expansion opportunities across lines of business and shape follow-on scope during engagements
• Build executive relationships to position Caylent as a long-term AI strategy partner
• Attend on-site for final Catalyst block: readout, workshop, and executive presentation

Internal Contribution

• Contribute reusable strategy frameworks, delivery artifacts, and methodology improvements back into the practice
• Lead cross-team AI strategy engagements and refine the architect-engineer delivery model and 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, or solutions architecture
• Ability to engage across lines of business and communicate with both technical and business audiences
• 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 and a Certified Claude Architect
• Experience running structured stakeholder interviews, discovery sessions, and facilitated workshops
• Strong executive communication skills (written and presentation)
• Experience delivering professional services engagements including scope management and client advisory
• Working knowledge of CI/CD pipelines, DevOps practices, and modern software development workflows

Preferred

• Experience mapping AI initiatives to business outcomes 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 (e.g., DORA, DevEx)
• Experience designing and facilitating workshops for mixed audiences

Who Thrives Here

• Leaders with prior engineering team or technology strategy experience inside product companies
• People who think across business functions and can converse with both COOs and engineers
• Practitioners who balance risk awareness with momentum and who drive account expansion
• Contributors who iterate on methodology and feed learnings back into the practice

Benefits

• 100% remote work
• Equitable Life - Hybrid Plan
• 100% premium coverage for employee and dependents
• Competitive phantom equity
• Long-term disability
• 4% pension match (employer contribution)
• Unlimited vacation, sick leave, paid holidays, and parental leave
• Paid for exams and certifications
• Peer bonus awards
• State-of-the-art laptop and tools; equipment & office stipend
• Individual professional development plan and annual learning & development stipend
• Work with a global team and inclusive culture

Compensation

• Base salary range: CAD 228,000 - CAD 253,000 per year (commensurate with experience)
• Additional compensation may include bonuses, commissions, equity, and other incentives

Travel & Work Authorization

• Role may require up to 50% travel depending on business needs
• Candidates must have current legal authorization to work in the country where the position is located; Caylent is not able to sponsor visas or work permits