DWX - Site Reliability & Automation Engineer

Group 1001 is a consumer-centric, technology-driven family of insurance companies on a mission to deliver outstanding value and operational performance by combining financial strength and stability with deep insurance expertise and a can-do culture. Group1001’s culture emphasizes the importance of collaboration, communication, core business focus, risk management, and striving for outcomes. This goal extends to how we hire and onboard our most valuable assets – our employees.

Why This Role Matters:

We're hiring for a role that doesn't exist on our team yet — and that's the point. Our Senior Solutions Engineers and Operations Engineers are exceptional. They build, they ship, they support, and they keep the business running. But they're carrying heavy workloads, and when you're heads-down delivering, you don't always have the space to step back and ask: should this be automated? Could AI do this safely? Where is the biggest leverage point in our environment?

That's the role. We need a dedicated DWX Site Reliability & Automation Engineer whose entire lens is automation, efficiency, and AI enablement — someone who frees our creators up to create. You won't be just another engineer in the queue. You'll be the engineer who looks at the queue and asks why it exists.

How You'll Contribute:

Across DWX, we have brilliant engineers solving complex problems — but too much of their time goes to repeatable work that shouldn't require a human. Manual provisioning steps. Recurring incident patterns that get patched instead of engineered out. Reporting that gets built by hand every quarter. Onboarding and offboarding flows with too many touchpoints. AI tools that could be helping the team, but aren't — because nobody has the bandwidth to figure out how to deploy them safely.

You will be the engineer dedicated to changing that. Your success will be measured in engineering hours given back, incidents prevented, and capabilities unlocked — not tickets closed.

What You'll Own:

You will own the automation and AI-enablement charter for DWX. That means:

Identifying the highest-leverage opportunities. You'll embed with our Solutions and Ops Engineers, observe the work, mine the ticket data, and find the patterns. You'll know where the toil lives and which automation will give the biggest return. You'll bring an SRE's instinct for measurement — toil quantification, error budgets, SLOs — to a function that's traditionally operated on gut and queue.

Building the automation. You'll engineer end-to-end automated workflows using modern IaC (Terraform, Bicep), CI/CD (Azure DevOps, GitHub Actions), configuration-as-code patterns, and orchestration platforms (Logic Apps, Power Automate, ServiceNow flows, custom services). Your code will be production-grade, version-controlled, peer-reviewed, observable, and resilient.

Enabling AI across the team, safely. You'll be the engineer responsible for figuring out how AI tools — Copilot, Claude, internal LLM platforms, agentic systems — get deployed across DWX in a way that's secure, compliant, and genuinely useful. That means defining patterns for AI-assisted troubleshooting, AI-augmented runbooks, prompt libraries, agent workflows, and the guardrails that make all of that defensible to Cybersecurity, Legal, and Compliance.

Driving reliability as a discipline. You'll bring SRE practice to DWX: meaningful SLIs and SLOs for the services that matter, observability that surfaces problems before users feel them, post-incident learning that produces durable fixes, and chaos/resilience thinking applied to the digital workplace. You'll partner with our Senior Support Manager on problem management — turning recurring incidents into automation backlog instead of ongoing pain.

Partnering broadly. You'll work alongside Solutions Engineers, Operations Engineers, the Microsoft Engineer, Cybersecurity, Networks, Architecture, Product Management, and Business Technology — not as a service provider but as a force multiplier. Your job is to make every one of them more effective.

What We're Looking For:

You've spent 7+ years in SRE, platform engineering, or DevOps roles, ideally with time in regulated environments — L&A, insurance, or financial services preferred. You've built and run real automation at scale, not just scripted around the edges. You can point to systems you've made measurably more reliable, processes you've eliminated through engineering, and teams you've made faster through tooling.

You bring expert-level command of:

• Infrastructure-as-code — Terraform, Bicep, ARM, or equivalent
• CI/CD pipelines — Azure DevOps, GitHub Actions, with real-world experience in testing, gating, and progressive delivery
• Scripting and development — PowerShell, Python, and at least one general-purpose language you'd ship production code in
• Git — branching strategies, code review discipline, repo hygiene
• Cloud platforms — Azure deeply; AWS or GCP a plus
• Observability — Azure Monitor, Log Analytics, KQL, Application Insights, or comparable stacks
• API and integration work — Graph API, REST, webhooks, event-driven patterns

You bring genuine, current depth in AI and automation:

• Hands-on experience deploying LLM-powered workflows in enterprise environments
• Understanding of agentic systems, MCP, retrieval-augmented patterns, and AI safety practices
• A point of view on which AI use cases are real and which are hype
• Experience with AI governance — prompt safety, data classification, output validation, audit trails

You bring the digital transformation mindset: you've helped organizations move from ticket-driven to product-driven operations, from runbook-driven to code-driven, from reactive to proactive. You can build the business case as well as the system.

Above all, you have the lens. You walk into an environment and see automation opportunities the way an architect sees load paths. You find fulfillment in making other engineers' lives better. You measure your day by the toil you eliminated, the AI capability you safely shipped, the reliability you quietly improved, and the user experience that got a little more seamless because of work no one will ever directly see.

Preferred Qualifications:

• Experience implementing SRE practice from scratch in an organization that didn't previously have it
• Background in platform engineering — building internal developer platforms, golden paths, paved roads
• AI/ML engineering experience beyond prompt-level work — fine-tuning, evaluation, RAG architectures, agent frameworks
• Certifications: Azure Solutions Architect Expert, Azure DevOps Engineer Expert, HashiCorp Terraform Associate, or equivalent
• Experience with ServiceNow scripting and flow designer at a meaningful depth
• Background contributing to or maintaining open source automation or SRE tooling
• Experience in regulated industries with appreciation for the compliance constraints around AI and automation

DWX is how our business experiences technology every day, and our engineers are the people making that real. But our engineers shouldn't be spending their best hours on work a system could do for them. We're investing in this role because we believe the next era of DWX is built on automation and AI — done thoughtfully, deployed safely, and grounded in genuine engineering craft.

We're looking for a true technologist who finds joy in this work. Someone who reads the latest on agentic AI on a Saturday morning, who has opinions about which automation pattern is right for which problem, who cares as much about the engineer experience as the end-user experience — because they understand those two things are the same problem viewed from different angles.

If that's you, we want to talk.

Compensation:  

Our compensation reflects the cost of labor across several U.S. geographic markets. The base pay for this position ranges from $180,000/year in our lowest geographic market up to $230,000/year plus bonus in our highest geographic market.  Pay is based on a number of factors including market location and may vary depending on job-related knowledge, skills, and experience.

Benefits Highlights:  

Employees who meet benefit eligibility guidelines and work 30 hours or more weekly, have the ability to enroll in Group 1001’s benefits package. Employees (and their families) are eligible to participate in the Company’s comprehensive health, dental, and vision insurance plan options.  Employees are also eligible for Basic and Supplemental Life Insurance, Short and Long-Term Disability. All employees (regardless of hours worked) have immediate access to the Company’s Employee Assistance Program and wellness programs—no enrollment is required.  Employees may also participate in the Company’s 401K plan, with matching contributions by the Company.

Group 1001, and its affiliated companies, is strongly committed to providing a supportive work environment where employee differences are valued. Diversity is an essential ingredient in making Group 1001 a welcoming place to work and is fundamental in building a high-performance team. Diversity embodies all the differences that make us unique individuals.  All employees share the responsibility for maintaining a workplace culture of dignity, respect, understanding and appreciation of individual and group differences.