Sycle is a market-leading global SaaS company with the mission of facilitating the delivery of better hearing to the world. Founded in 2001, we have grown to be the leading practice management solution for audiology (hearing care) providers, with more than 65% market share.

Position Requirements

As a vital part of the Sycle Team, the Customer Experience team strives to provide our customers with a level of support that exceeds expectations. The role involves supporting our audiology platform, helping customers learn the system, and leveraging its functionality over the phone and email. Inquiries range from base-level technical troubleshooting—such as investigating software "oddities" and connectivity issues—to complex billing and medical insurance inquiries. Someone with experience and/or certifications in the medical insurance space, coupled with a natural aptitude for technical problem-solving, is a requirement for this role. While 80% of the work is technical support the 20% that relates to medical billing support is critical to this role. 

This is a remote position that requires the applicant to work from home from one of the following states: AL, CA, CO, FL, IL, MN, NV, OR, TX or UT.

Key Competencies Required

• Customer Focused: Serve as the front line for Sycle customers, managing inquiries and helping them maximize the software's value, including supporting technical workflows and complex billing/insurance inquiries.
• Communication Skills: Ability to effectively listen and communicate technical and insurance-related concepts with Sycle customers and the internal team.
• Learning Ability: Must be a quick learner with the ability to master our core software, ancillary products, and technical diagnostic tools to effectively support users.
• Technical Detective & Teamwork: Proactively take the lead in identifying the root cause of customers' technical issues—from browser conflicts to sync errors—while partnering well with critical functions like Customer Service and Marketing.

Skills and Knowledge

• Experience with medical claims, terminology, and billing principles (CPT, HCPCS, ICD-10).
• Technical Troubleshooting: Familiarity with basic diagnostic concepts, such as checking connectivity via trace routes or identifying failures within software error logs in Windows and Mac environments.
• Browser Environment Management: Proficiency in optimizing a variety of browsers for SaaS performance, including clearing cache, setting file associations, and managing plugins/pop-up exceptions.
• Systems Literacy: Experience navigating various CRM, EMR, or EHR databases and understanding the flow of data between practice management tools and clearinghouses.

Position Responsibilities

• Understand Sycle platform functionality and communicate technical and billing information succinctly to customers.
• Build professional relationships to maintain customer satisfaction.
• Provide basic training and technical environment setup for new Sycle users.
• Manage account maintenance, including clinic additions, billing updates, and subscription renewals.
• Identify problematic workflows and investigate software "odd behaviors" to determine if they are user-error or system defects.
• Report core functionality suggestions through detailed feature requests.
• Provide browser support and troubleshoot software integration syncs.
• Understand reporting functions and remain informed on software defects to help troubleshoot with customers.
• Effectively manage cases through HubSpot and escalate complex issues with clear technical documentation (screenshots and logs).

Basic Qualifications

• 2-3+ years of technical help desk or technical billing support experience.
• Strong problem analysis and root-cause troubleshooting skills.
• High energy with a results-driven, "self-starter" personality.
• Strong verbal and written communication skills.
• Like to have: AAPC certification or CPB in Professional Billing.

Nice to Have

• Experience working with Waystar and/or Optum Intelligent EDI.
• Experience troubleshooting SFTP or bi-directional clearinghouse data flows.

This fully-remote role at Sycle offers a competitive hourly wage, internet subsidy and Sycle’s benefits plan. If you’re a strong fit for this role and live in the following US states:  AL, CA, CO, FL, IL, MN, NV, OR, TX or UT please apply. Due to the number of applications we expect to receive, only successful candidates will be contacted.

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!