Manager of DevOps (Agentic)

About Sycle At Sycle, we’re transforming how audiology practices operate. Our cloud-based practice management platform powers over 20,000 users worldwide—from local clinics to enterprise retailers. We’re a growing SaaS company with startup energy, industry respect, and global reach. The Opportunity Over the last year, we’ve integrated AI agents into our DevOps workflows. We have working LLM pipelines for log triage and Terraform drafts, with a roadmap to expand into IAM auditing and self-healing systems. We are seeking a Manager of DevOps to serve as the "Right Hand" to the Director of Infrastructure. You will own the day-to-day execution of the DevOps roadmap and manage our 4–6 person engineering team, allowing the Director to focus on long-term strategy and cross-organizational platform work. What we mean by "Agentic": We use AI agents to handle the initial heavy lifting, like drafting infra changes, analyzing incidents, and writing runbooks. Our engineers always review the work and own the final results. Your role is to engineer this exact workflow. You will ensure the handoff between AI generation and human review is secure, highly reliable, and built for speed in production. Tech Stack & Tools Cloud & Infrastructure: AWS (Multi-account), Fargate, EKS/ECS (mid-migration), Terraform, Aurora MySQL. CI/CD & Ops: Bitbucket Pipelines, Cloudflare, New Relic, Sumo Logic. Agentic Tooling: Claude, Windsurf, and internal agent harnesses for log analysis, Terraform generation, and IAM policy review. Key Pillars of Responsibility Roadmap & Project Delivery: Translate the Director’s strategy into actionable quarterly roadmaps. You are a "deliverer" who holds the team to milestone dates and ensures platform work stays in sync with product release windows. Team Leadership & Coaching: Manage a distributed team of 4-6 mid-to-senior DevOps engineers. You will run 1:1s, set performance goals, and most importantly, coach the team through the cultural and technical shift from manual scripting to agent-assisted work. Cross-Functional Partnership: You are the bridge between the platform and the rest of the company: Engineering: Partner with Dev Leads on "paved road" tooling and self-service CI/CD Security/Compliance: Own audit-readiness for SOC 2 and HIPAA infrastructure controls Finance: Lead practical FinOps wins and AWS cost forecasting Customer Success: Act as the operational point of contact during Sev-1 events Agentic Program Ownership: Define the guardrails for AI usage. You own the prompts, context packs, and rules that make our agents reliable. You set the policy for human-in-the-loop reviews and ensure data privacy (HIPAA/SOC 2) in all LLM workflows. Operational Excellence: Accountable owner for production stability (99.9% uptime SLO). You oversee the on-call program, participate in the rotation, run incident reviews, and manage the corrective-action backlog. Skills & Requirements SaaS Engineering Mastery: 5-8+ years running production SaaS infrastructure on AWS, with deep hands-on expertise in Terraform and container orchestration (EKS/ECS). People Management: 2-4+ years of experience managing engineering teams. You have a proven ability to motivate technical talent and manage performance in a remote, distributed environment. Project Leadership: A clear track record of building technical roadmaps and shipping platform work to specific dates. You are honest with stakeholders and proactive about managing slips. Agentic Proficiency: Practical experience using AI agents (Claude, Windsurf, etc.) to produce real engineering output. You have a point of view on where agents help and where they require rigorous human oversight. Accountability: You take 100% responsibility for the integrity of the system, whether a change was drafted by a human or an agent. Collaborative Mindset: You enjoy working with developers and believe the best DevOps teams create "paved roads," not roadblocks. What Success Looks Like In 90 Days: You have audited all active agent workflows, built trust with engineering leads, and have a 6-month execution plan signed off by the Director. In 6 Months: Dev teams report that DevOps is "easier to work with" due to improved self-service tooling. Multiple manual workflows are now running agent-first with measurable quality gains. In 12 Months: Infrastructure delivery throughput is significantly higher than today’s baseline. The Director is fully focused on strategic work because you have full command of day-to-day execution. Benefits Comprehensive personal health plan (Medical, Dental, Vision). RRSP matching and Internet subsidy. 3+ weeks of paid time off plus paid statutory holidays. Location: Remote-first culture (Hiring in BC or ON) If you you're currently based in BC or Ontario and meet at least 80% of the requirements, please apply!