Forward Deployed AI Lead

Posted 15 hours ago

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About the role

  • Forward Deployed AI Lead shaping Anthropic AI strategies and operating models for Caylent cloud-services clients. Directing FDE implementation, executive workshops, adoption roadmaps, and account expansion.

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
  • Design AI operating models defining how organizations adopt, govern, and scale AI across the business
  • Define AI outcome maps tying initiatives to measurable business results
  • Lead AI maturity assessments and architect adoption roadmaps aligned to Anthropic’s platform capabilities
  • Facilitate executive workshops and enablement sessions
  • Deliver executive presentations covering current-state findings, ROI projections, and strategic recommendations
  • Direct FDE work on Claude Code tooling, prompt architecture, and workflow automation
  • Identify expansion opportunities across lines of business
  • Shape follow-on scope throughout engagements
  • Build executive relationships positioning Caylent as a long-term AI strategy partner
  • Attend onsite for the final Catalyst block, including readout, workshop, and executive presentation
  • Contribute reusable strategy frameworks, delivery artifacts, and methodology improvements
  • Lead AI strategy engagements spanning multiple teams, platforms, and business functions
  • Collaborate with FDEs to refine the architect-engineer delivery model and handoff patterns

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
  • 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
  • Certified Claude Architect
  • Experience running structured stakeholder interviews, discovery sessions, and facilitated workshops with technical and business audiences
  • Strong executive communication, including 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
  • Current legal authorization to work in the country where the position is located; Caylent cannot sponsor visa or work permit applications
  • Preferred: Experience mapping AI initiatives to business outcomes with executive-level ROI framing
  • Preferred: Familiarity with PE portfolio company environments 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 Claude Code’s extensibility model
  • Preferred: Familiarity with SDLC maturity frameworks or workforce analytics (DORA, DevEx)
  • Preferred: Experience designing and facilitating workshops for mixed 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
  • Paid 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
  • Work with an amazing worldwide team and in an incredible corporate culture
  • May require up to 50% travel, depending on business needs

Job title

Job type

Full Time

Experience level

Senior

Salary

CA$228,000 - CA$253,000 per year

Degree requirement

No Education Requirement

Tech skills

SDLC

Location requirements

RemoteCanada

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