Forward Deployed AI Strategist at Caylent in Canada

Caylent is a cloud native services company that helps organizations bring the best out of their people and technology using Amazon Web Services (AWS). We provide a full-range of AWS services including workload migrations and modernization, cloud native application development, DevOps, data engineering, security and compliance, and everything in between. At Caylent, our people always come first.  We are a global company and operate fully remote with employees in Canada, the United States, and Latin America. We celebrate the culture of each of our team members and foster a community of technological curiosity. Come talk to us to learn more about what it means to be a Caylien! About This Role Caylent's Anthropic Enablement & Engineering (AE2) practice is a dedicated AI services team built in partnership with Anthropic. We were Anthropic's first pure-play delivery partner, and are working closely with them to define the next evolution of Software Development. The Forward Deployed AI Strategist leads the work that defines what transformation looks like before a single Architect is deployed. You own blueprint engagements — comprehensive assessments of how an organization builds software across the full SDLC and PDLC, where AI can change the economics, and what a credible multi-phase roadmap looks like. You then lead the execution programs that follow, coordinating Agentic Architects across parallel workstreams and driving outcomes against the plan you set. On engagements where scope and timeline call for it, you step in part-time as an Agentic Architect. Your clients are PE portfolio companies, growth-stage software businesses, and enterprise engineering organizations where transformation decisions are made at the C-suite and board level. What You'll Do Transformation Strategy Lead AI transformation blueprint engagements: current-state assessment across SDLC and PDLC, gap analysis, and prioritized initiative roadmap Run executive discovery with CTOs, CPOs, and VP Engineering to surface strategic goals, constraints, and success criteria Assess AI adoption posture across engineering and product functions — tooling, workflows, org design, delivery practices Define initiative sequencing: what to address first, what to automate, where to standardize Develop board-ready transformation cases that connect AI investment to PE value creation metrics — revenue per head, time-to-feature, delivery predictability Facilitate executive alignment workshops that move stakeholders from awareness to decision Execution Leadership Lead multi-team AI transformation programs following blueprint delivery Coordinate Agentic Architects across parallel workstreams; translate roadmap priorities into sprint-level milestones and delivery plans Own the executive-sponsor relationship through delivery close Step into Agentic Architect responsibilities on engagements where hands-on execution is required Business Development Shape follow-on scope throughout blueprint delivery — by handoff you have a working hypothesis for the execution program Present the execution proposal at blueprint readout Surface expansion signals across the client organization and route them to the account team Internal Contribution Codify transformation methodology: translate blueprint and execution patterns into reusable frameworks for the practice Mentor Agentic Architects on executive engagement, strategic framing, and scoping What We're Looking For Required Significant experience across 12+ years across software development, technical consulting, or a combination, with demonstrable knowledge / experience on both SDLC and PDLC sides of a software organization Proven success 5+ years leading transformation, strategy, or technical advisory engagements with engineering and product organizations Hands-on experience with Claude Code or equivalent AI-assisted development tools in a real workflow Experience building and presenting technology transformation roadmaps to C-level and board audiences Strong working knowledge of modern SDLC (CI/CD, DevOps, cloud-native) and product development (agile delivery, roadmapping, product operations) Experience sizing and sequencing multi-team, multi-quarter transformation programs Prior professional services delivery experience with scope ownership and deliverable accountability Preferred Certified Claude Architect Background in PE or growth-equity-backed software companies — understand value creation timelines and board expectations Experience leading programs that span engineering and product simultaneously Familiarity with developer experience and delivery metrics frameworks (DORA, DevEx, SPACE) Experience designing AI governance and adoption guardrails for enterprise organizations Direct experience building or operating agentic AI systems in production Who Thrives Here Thinks in roadmaps, not tasks. You see where an organization needs to be 12 months from now and can build a credible path to get there. Strategy that isn't accountable to outcomes is not strategy. Can still do the work. You use Claude for all of your work. You'll step into Agentic Architect engagements when the situation calls for it. Seniority here means broader scope, not distance from delivery. Credible at the board level. You've presented transformation cases to PE sponsors and C-suites and know how to connect technical decisions to business value without hand-waving. Makes the methodology better. Every blueprint you run should make the next one faster. You feed patterns back into the practice rather than keeping them in your head. Multiplies Architects. You can set direction, coordinate execution, and step back. You know what effective oversight looks like versus micromanagement. This is a poor fit for purely advisory profiles. You own outcomes, not just recommendations. Why This Team Ground floor of something real: this BU is early, well-resourced, and anchored to Anthropic. You're writing the playbook, not inheriting one Define the methodology: you are shaping how AI transformation gets scoped and delivered at scale. The frameworks you build here will drive how this practice grows Proximity to the PE channel: your clients are PE portcos and enterprise engineering orgs at the frontier of AI adoption where transformation decisions are being made now Revenue upside: Strategists who drive account expansion earn on revenue generated, not just delivery margin AI-native by default: this team uses AI in how it works. Specification-First Engineering is how we move from prototype to production fast Outcomes, not hours: advancement tied to delivery performance and account growth, not utilization 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 Base Salary Range: The expected base salary range for this position is CAD $215,000 - $235,000per 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. NOTE: We’re unable to provide visa sponsorship now or at any time in the future. At Caylent, we are committed to fair, transparent, and inclusive hiring practices. As part of our recruitment process, we may use artificial intelligence (AI) tools or automated systems to assist with the screening and evaluation of applications to help match candidate qualifications with job requirements. These tools are designed to support — not replace — human decision-making. Final hiring decisions are always made by our trained recruitment professionals. If an AI or automated tool is used during your application process, it will only be in accordance with applicable laws and regulations, and your information will be handled in a secure and confidential manner. If you have any questions, please contact talent@caylent.com Caylent is a place where everyone belongs. We celebrate diversity and are committed to creating an inclusive environment for all employees. Our approach helps us to build a winning team that represents a variety of backgrounds, perspectives, and abilities. So, regardless of how your diversity expresses itself, you can find a home here at Caylent. We are proud to be an equal opportunity employer. We prohibit discrimination and harassment of any kind based on race, color, religion, national origin, sex (including pregnancy), sexual orientation, gender identity, gender expression, age, veteran status, genetic information, disability, or other applicable legally protected characteristics. If you would like to request an accommodation due to a disability, please contact us at hr@caylent.com.