[Hiring] Forward Deployed AI Lead @Caylent

Role Description

Caylent’s Anthropic Business Unit is a dedicated AI services practice built in partnership with Anthropic. The Forward Deployed AI Lead is the strategic and architectural lead on AI engagements. Paired with a Forward Deployed Engineer (FDE) who handles hands-on implementation, you own the engagement arc:

• Shaping AI strategy
• Designing operating models
• Mapping AI outcomes to business value
• Guiding executive stakeholders through adoption

This is a cross-functional role. You engage across lines of business, connecting AI initiatives to the outcomes that matter to each part of the organization. Every engagement is anchored to Anthropic’s platform and focused on real AI adoption outcomes.

Your clients span PE portfolio companies, growth-stage software businesses, and enterprise organizations. You are the strategic face of Caylent from kickoff through handoff.

What You’ll Do

Strategy and Architecture

• 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 to map organizational context, AI readiness, and strategic goals across lines of business
• Design AI operating models that define how the organization adopts, governs, and scales AI
• Define AI outcome maps that tie initiatives to measurable business results: efficiency gains, revenue impact, risk reduction, and time-to-value
• Lead AI maturity assessments and architect near-term and long-term adoption roadmaps aligned to Anthropic’s platform capabilities
• Facilitate executive workshops and enablement sessions for audiences ranging from engineering teams to C-suite leaders
• Deliver executive presentations to CTOs, VPs of Engineering, and line-of-business leaders covering current-state findings, ROI projections, and strategic recommendations
• Direct FDE work on Claude Code tooling, prompt architecture, and workflow automation

Client Relationship and Business Development

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

Internal Contribution

• Contribute reusable strategy frameworks, delivery artifacts, and methodology improvements back into the practice at engagement close
• Lead AI strategy engagements spanning multiple teams, platforms, and business functions
• Collaborate with FDEs to refine the architect-engineer delivery model and improve handoff patterns

Qualifications

• 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
• Strong executive communication: 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

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 (DORA, DevEx)
• Experience designing and facilitating workshops for mixed audiences

Who Thrives Here

• Sat in the seat: You’ve led engineering teams or technology strategy inside a product company
• Thinks across the business: You see how AI impacts operations, product, and go-to-market
• Knows when to slow down: You surface risks before committing to an approach
• Closes the next engagement: You treat the final week of a Catalyst as a conversion window
• Makes the methodology better: You feed back learnings into the practice
• Earns trust at the executive level: Comfortable presenting to both technical and business audiences

Why This Team

• Ground floor of something real: this BU is early, well-resourced, and anchored to Anthropic
• Own the methodology: you are shaping how AI-DLC enablement gets delivered
• Proximity to the market: your clients are at the frontier of AI adoption
• Revenue upside: Forward Deployed AI Lead who drive account expansion earn on revenue generated
• AI-native by default: this team uses AI in how it works
• Outcomes, not hours: advancement tied to delivery performance and account growth

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
• This role may require up to 50% travel, depending on business needs

Base Salary Range

The expected base salary range for this position is CAD $228,000 - $253,000 per year, commensurate with experience and qualifications.

Additional Compensation Components

In addition to the base salary, the compensation package may include bonuses, commissions, equity, and other incentives. The specific components will vary depending on the role and individual and/or company performance.

Company Description

At Caylent, we are committed to fair, transparent, and inclusive hiring practices. We celebrate diversity and are committed to creating an inclusive environment for all employees.