[Hiring] Senior Tooling and Automation Engineer @The Redesign Group

Role Description

The Senior Tooling and Automation Engineer is a hands-on builder who owns how the Managed Services tooling ecosystem works as one connected system. You will write the integrations, automations, skills, and apps that link our RMM, network monitoring, backup reporting, and service management platforms, using AI-assisted development as your primary way of producing code. You will own Jira Service Management configuration end to end, own the alerting lifecycle so the team acts only on meaningful signals, and serve as the senior escalation point when any piece of tooling fails.

Each core platform has an administrator who runs it day to day; you own the connective layer between them and the standards for how they alert, integrate, and roll out to customers, and you work with each administrator on changes inside their tool. Where the stack has a gap, you lead the build-or-buy decision from business justification through evaluation and rollout. We will ask you to show working code you have built with AI assistance, because that is how this job gets done.

Qualifications

• Demonstrated fluency with AI-assisted coding tools (Claude, Cursor, Replit, or similar) to produce working, maintainable code, with examples you can walk us through.
• Hands-on experience building integrations using REST APIs, webhooks, and structured data (JSON, XML), including common authentication methods.
• Scripting and development capability in a language such as Python, PowerShell, or JavaScript, with working use of Git for source control.
• Experience administering Jira Service Management or a comparable ITSM platform, including workflows, request types, and automations.
• Working knowledge of RMM, network monitoring, and backup tooling, and experience tuning alerting to cut noise.
• Solid understanding of ITIL and change management, with the ability to execute within a structured framework.
• Strong troubleshooting skills across platforms, integrations, and automation, and a clear, customer-facing communication style.

Requirements

• Design, build, and maintain integrations between platforms using APIs, webhooks, and email, writing the connecting code, skills, and apps with AI-assisted development tools.
• Own Jira Service Management configuration, including screens, workflows, custom ticket and request types, automations, and queues.
• Identify noise across the alerting cycle, human and system, and tune the stack so only actionable alerts reach the team.
• Serve as the senior escalation point for tooling failures, including broken integrations, misbehaving automation, authored scripts, and alerts firing on false positives.
• Set and enforce the standards for how core tooling integrates and alerts, working with each platform's administrator on changes inside their tool.
• Identify gaps in the tooling stack and lead the build-or-buy decision, including business justification, evaluation, and end-to-end rollout of new tools.
• Ensure every customer's tooling is fully rolled out and tuned to their environment, including custom OS patching and observability alerting policies agreed with the customer.
• Explain our tooling to customers in plain terms: what it does, how it installs, and its impact on their environment.
• Produce service level objective, utilization, and operational reporting for delivery leadership from tooling data.
• Execute all work within an ITIL-aligned change management framework and keep integrations, automations, and configuration documented so the environment is auditable and not dependent on one person.

Preferred Qualifications

• Direct experience with NinjaOne, Auvik, Bocada Cloud, or Jira Service Management.
• Experience leading tool evaluations and vendor selection, including proof-of-concept work and business justification.
• Familiarity with workflow-automation or iPaaS platforms.

Background

• 5+ years in an MSP or enterprise IT environment focused on tooling, automation, or systems integration, in roles where you built and owned the integrations rather than only used the tools.
• Experience as the first or only person responsible for a whole tooling stack, since each of our core platforms already has an administrator and you will set the standard rather than inherit one.
• Bachelor's degree in information technology or a related field, or equivalent hands-on experience.

Benefits

• Medical, Dental, and Vision Insurance
• 401(k) retirement plan with company match (annual dollar cap applied)
• Flexible time off plan
• 15 paid holidays
• Sick leave (amount varies by state requirements and is at least the minimum required by any state)
• Short-term and long-term disability
• Life insurance
• Paid parental leave