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Forward Deployed AI Lead

1 month ago
Canada
Full-time
Lead
AI (Artificial Intelligence)
Artificial Intelligence and Machine Learning
AWS CI/CD Generative AI Microservices
Apply Now
Caylent

Caylent

Caylent is a cloud native services company that simplifies AWS cloud adoption with a user-friendly DevOps platform for scalable cloud environments.

IT Services
251-1K
Founded 2015
$16M raised
View All Jobs 27

Description

  • Own AI engagements end-to-end as the strategic lead, from discovery through executive handoff, in partnership with a Forward Deployed Engineer.
  • Run structured discovery with engineering, product, and business stakeholders to assess context, readiness, and goals.
  • Design AI operating models that define how organizations adopt, govern, and scale AI across the business.
  • Map AI initiatives to measurable business outcomes such as efficiency gains, revenue impact, risk reduction, and time-to-value.
  • Lead AI maturity assessments and build near-term and long-term adoption roadmaps aligned to Anthropic’s platform capabilities.
  • Facilitate executive workshops, enablement sessions, and presentations for technical and business audiences.
  • Direct FDE work on Claude Code tooling, prompt architecture, and workflow automation.
  • Identify expansion opportunities and shape follow-on scope throughout the engagement.
  • Build executive relationships that position Caylent as a long-term AI strategy partner.
  • Contribute reusable frameworks, delivery artifacts, and methodology improvements back into the practice.

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 with both technical and business stakeholders.
  • 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.
  • Strong executive communication skills, including writing and presenting to CTOs, VPs of Engineering, and business leaders.
  • Experience delivering professional services engagements with scope management, deliverable ownership, and client advisory.
  • Working knowledge of CI/CD pipelines, DevOps practices, and modern software development workflows.
  • 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 such as DORA or DevEx (preferred).

Benefits

  • 100% remote work.
  • Equitable Life - Hybrid Plan.
  • 100% premium coverage for the employee and dependents.
  • Competitive phantom equity.
  • Long-Term Disability coverage.
  • 4% pension match (employer contribution).
  • Unlimited vacations, plus sick leave and paid holidays.
  • Parental leave.
  • Paid exams and certifications.
  • Peer bonus awards.
  • State-of-the-art laptop and tools, plus equipment and office stipend.
  • Individual professional development plan and annual learning and development stipend.
  • Base salary range of CAD $228,000 to $253,000 per year.
  • Additional compensation may include bonuses, commissions, equity, and other incentives.
  • Up to 50% travel, depending on business needs.

Interested in this position?

Apply directly on the company website

Apply Now

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