Remote opportunity at
CaylentForward Deployed AI Lead
Caylent is seeking a Forward Deployed AI Lead to act as the strategic and architectural head on client artificial intelligence engagements. In partnership with a Forward…
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About This Role
Caylent is seeking a Forward Deployed AI Lead to act as the strategic and architectural head on client artificial intelligence engagements. In partnership with a Forward Deployed Engineer handling implementation, this professional owns the entire lifecycle of an engagement from initial discovery through executive handoff. The company functions as an AI-first cloud services provider and an AWS Premier Tier Services Partner, operating as a fully remote global organization with team…
Job Description
Caylent is seeking a Forward Deployed AI Lead to act as the strategic and architectural head on client artificial intelligence engagements. In partnership with a Forward Deployed Engineer handling implementation, this professional owns the entire lifecycle of an engagement from initial discovery through executive handoff. The company functions as an AI-first cloud services provider and an AWS Premier Tier Services Partner, operating as a fully remote global organization with team members distributed across the United States, Canada, and Latin America.
This position demands a cross-functional approach that connects artificial intelligence initiatives to concrete business results for various clientele, including private equity portfolio companies, growth-stage software firms, and enterprise corporations. The person in this role runs structured discovery sessions, designs AI operating models, establishes outcome maps tied to business value, and leads workshops for technical and executive audiences. Additionally, the lead directs engineering tasks related to tooling and prompt architecture while driving account expansion and contributing reusable frameworks to the internal practice.
The ideal candidate possesses extensive software development and technical architecture background, combined with leadership experience and the capability to communicate effectively with both engineering teams and C-suite executives. Candidates must possess authorization to work in the hiring country, as visa sponsorship is unavailable.
Responsibilities
- Manage AI engagements end-to-end from discovery to executive handoff alongside an implementation engineer
- Conduct structured discovery sessions across different business lines to evaluate organizational context, AI readiness, and goals
- Design AI operating models that govern how businesses adopt and scale artificial intelligence
- Establish outcome maps connecting technology initiatives to measurable business gains such as efficiency, revenue, risk reduction, and time-to-value
- Lead maturity assessments and build near-term and long-term adoption roadmaps tied to Anthropic platform capabilities
- Facilitate executive workshops, enablement sessions, and presentations for audiences ranging from engineering teams to C-suite leaders
- Direct engineering work on prompt architecture, workflow automation, and Claude Code tooling
- Identify account expansion opportunities and cultivate long-term client partnerships
- Contribute reusable strategy frameworks and methodology improvements back into the practice
Requirements
- Over eight years of software development or technical architecture experience across diverse technology stacks and hyperscaler environments
- Minimum of three years in engineering leadership, solutions architecture, technical consulting, or a combined background
- Demonstrated capability to communicate across lines of business with both technical personnel and operational executives
- Experience designing or advising on digital transformation programs, technology adoption strategies, or AI operating models
- Hands-on familiarity with Claude Code or equivalent AI-assisted development tooling
- Experience running structured stakeholder interviews and facilitated workshops
- Strong executive communication skills with a history of writing and presenting to technical and business leaders
- Background in delivering professional services engagements with ownership over scope and deliverables
- Working knowledge of DevOps practices, CI/CD pipelines, and modern software development workflows
- Current legal authorization to work in the country where the position is located
Qualifications
- Certified Claude Architect designation
- Experience framing executive-level ROI by mapping artificial intelligence initiatives to business outcomes
- Familiarity with private equity portfolio company environments and board-level communication
- Background in enterprise technology strategy, platform engineering, or solutions architecture
- Experience with agentic AI workflow design, LLM prompt engineering, or AI product development
- Direct familiarity with the extensibility model of Claude Code
- Understanding of workforce analytics or software development lifecycle maturity frameworks
- Experience designing workshops for mixed audiences of engineers, product managers, and business stakeholders
Core Skills
Benefits
- Equitable Life Hybrid Plan with 100% premium coverage for employees and dependents
- Competitive phantom equity and revenue-based earning incentives
- Long-Term Disability coverage
- Four percent employer pension match
- Unlimited vacation time and sick leave
- Paid holidays and parental leave
- Financial coverage for exams and professional certifications
- Peer bonus awards
- State-of-the-art laptop, tools, and an equipment and office stipend
- Individual professional development plan and annual learning stipend
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
What is the remote work policy for this role?
Caylent operates as a fully remote global company, though this role may require up to 50 percent travel depending on business needs, including on-site attendance for the final Catalyst block.
What is the salary range for the Forward Deployed AI Lead position?
The expected base salary range is between CAD $228,000 and $253,000 per year, determined by experience and qualifications, with additional compensation components that may include bonuses, commissions, and equity.
Does Caylent offer visa sponsorship for this position?
No. The posting specifies that candidates must have current legal authorization to work in the country where the position is located, as visa or work permit applications cannot be sponsored at this time.
What level of experience is required?
Candidates must have over eight years of software development or technical architecture experience across varied stacks, along with at least three years in engineering leadership, technical consulting, solutions architecture, or a combination of these fields.
Sample Interview Questions
AI-generated questions tailored to this specific role — a preview of the full practice set.