other
Posted May 7Forward Deployed AI Strategist
at Caylent
United StatesOn-site
Responsibilities
- 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
- 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
- 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
- Present the execution proposal at blueprint readout
- 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
- 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
Requirements
- 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.
- Caylent's Anthropic Enablement & Engineering (AE2) practice is a dedicated AI services team built in partnership with Anthropic.
- 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.
- Assess AI adoption posture across engineering and product functions — tooling, workflows, org design, delivery practices
- 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
- experience with Claude Code or equivalent AI-assisted development tools in a real workflow •
- Strong working knowledge of modern SDLC (CI/CD, DevOps, cloud-native) and product development (agile delivery, roadmapping, product operations) •
- experience with scope ownership and deliverable accountability Preferred
- Experience leading programs that span engineering and product simultaneously
- Familiarity with developer
- Experience designing AI governance and adoption guardrails for enterprise organizations Direct
- experience building or operating agentic AI systems in production Who Thrives Here
- 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
- AI-native by default: this team uses AI in how it works. Specification-First Engineering is how we move from prototype to production fast
- 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
- 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.
Experience
- Proven success 5+ years leading transformation, strategy, or technical advisory engagements with engineering and product organizations Hands-on
Benefits
- Medical Insurance for you and eligible dependents 100% remote work
- 401k plan with company match up to 4% and immediate vesting
- Competitive phantom equity
- Dental and Vision insurance
- Term Disability Insurance Term Life Insurance
- Equipment & Office Stipend
- Annual stipend for Learning and Development
- Unlimited Paid Time Off, following a 90-day probationary period 10 Paid Holidays
- Base Salary Range: The expected base salary range for this position is $185,000 - $210,000 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.
- NOTE: We’re unable to provide visa sponsorship now or at any time in the future.
Contact
- If you have any questions, please contact talent@caylent.com
- If you would like to request an accommodation due to a disability, please contact us at hr@caylent.com.
Additional details
- 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
- We were Anthropic's first pure-play delivery partner, and are working closely with them to define the next evolution of Software Development.
- 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
- responsibilities on engagements where hands-on execution is required
- Shape follow-on scope throughout blueprint delivery — by handoff you have a working hypothesis for the execution program
- Surface expansion signals across the client organization and route them to the account team