Lead, Forward Deployed AI

This is a fully remote position, open to applicants in United States.

📋 Description

• Take ownership of AI projects from start to finish as the strategic lead, collaborating with an FDE who manages implementation.

• Conduct structured discovery sessions with engineering, product, and business stakeholders.

• Create AI operating models that support organizational adoption, governance, and scalability.

• Establish AI outcome maps that are linked to quantifiable business results.

• Lead assessments of AI maturity and design adoption roadmaps that align with Anthropic’s platform.

• Facilitate workshops and enablement sessions for executives.

• Present findings, ROI forecasts, and strategic recommendations to executives.

• Guide FDE efforts related to Claude Code tooling, prompt architecture, and workflow automation.

• Identify opportunities for expansion across various business lines.

• Shape follow-up scopes throughout engagements.

• Build executive relationships to position Caylent as a trusted long-term AI strategy partner.

• Participate on-site for the final Catalyst block.

• Contribute to reusable strategy frameworks, delivery artifacts, and enhancements to methodology.

• Lead AI strategy initiatives that span multiple teams, platforms, and business functions.

• Work with FDEs to improve the architect-engineer delivery model and handoff processes.

⛳️ Requirements

• Over 8 years of experience in software development or technical architecture across diverse stacks, including hyperscaler environments.

• At least 3 years in engineering leadership, technical consulting, solutions architecture, or a combination of these roles.

• Capability to engage across various business lines and effectively communicate with both technical and business executives.

• Experience in designing or advising on AI operating models, technology adoption strategies, or digital transformation initiatives.

• Hands-on experience with Claude Code or similar AI-assisted development tools.

• Certified Claude Architect.

• Proven experience conducting structured stakeholder interviews, discovery sessions, and facilitated workshops with both technical and business audiences.

• Strong executive communication skills, including the ability to write and present to CTOs, VPs of Engineering, and line-of-business leaders.

• Experience in delivering professional services engagements, encompassing scope management, deliverable ownership, and client advisory.

• Working knowledge of CI/CD pipelines, DevOps practices, and contemporary software development workflows.

• Legal authorization to work in the country where the position is located.

• No visa sponsorship is available.

• Preferred: experience in mapping AI initiatives to business outcomes with an emphasis on executive-level ROI framing.

• Preferred: familiarity with private equity portfolio company environments and communication at the board level.

• 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 the extensibility model of Claude Code.

• Preferred: familiarity with SDLC maturity frameworks or workforce analytics (DORA, DevEx).

• Preferred: experience in designing and facilitating workshops for diverse audiences.

🏝️ Benefits

• Medical insurance for you and eligible dependents.

• 401k plan with a company match of up to 4% and immediate vesting.

• Competitive phantom equity.

• Company-issued laptop.

• Dental and vision insurance.

• Term disability and life insurance.

• Flexible Spending Account.

• Equipment and office stipend.

• Annual stipend for learning and development.

• Unlimited paid time off.

• 10 paid holidays.

• Revenue-based compensation for account expansion.

• Opportunities for advancement linked to delivery performance and account growth.

• Flexible remote work arrangement.