Works directly with Anthropic Claude and Claude Code; focuses on directing FDEs on prompt engineering and agentic AI workflows while leading AI strategy and rapid adoption.

About the Role The Forward Deployed AI Lead at Caylent is the strategic and architectural owner of AI engagements, partnering with Forward Deployed Engineers to shape AI strategy, operating models, and adoption roadmaps anchored to Anthropic’s Claude platform. The role is client-facing, responsible for executive communication, workshop facilitation, and driving account expansion from discovery through handoff.

Job Description 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 wide-ranging 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

Equitable Life - Hybrid Plan

100% premium coverage for employee and dependents

Long-term disability

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

📌 Forward Deployed AI Lead (Winnipeg)
🏢 Vibehackers
📍 Winnipeg