Senior IT Systems Engineer, AI and Automation at Thumbtack

Challenge

As a Senior IT Systems Engineer on the IT Systems Architecture team, you’ll design and build the internal platforms, automation frameworks, and AI-enabled systems that power how Thumbtack employees work, including emerging patterns like agent-driven workflows and system orchestration. This role goes beyond traditional systems administration — you will help evolve IT Infrastructure into a scalable, automation-driven platform that enables employees and teams to operate efficiently and securely. You will play a key role in advancing automation and AI enablement across IT by integrating AI capabilities into workflows, building intelligent automations, and developing systems that reduce manual effort and improve how work gets done at scale.

You’ll partner closely with engineers, program managers, leaders, and cross-functional teams to deliver high-impact solutions across identity, SaaS platforms, cloud systems, and endpoint management. A core part of this role is designing and building scalable automation and integration frameworks — leveraging tools such as Okta Workflows, APIs, and custom connectors to create event-driven workflows and enable self-service capabilities across internal systems. You will help drive the convergence of automation and AI by identifying opportunities to streamline operations, connect systems more intelligently, and enable emerging patterns such as actions, orchestration, and system-driven workflows.

As a force multiplier, you’ll leverage your expertise in systems architecture, workflow automation, cloud services, authentication and access systems, and security to solve challenges across both day-to-day operations and longer-term strategic initiatives. You are a strong technical leader and communicator with a passion for building scalable platforms, mentoring others, and delivering high-quality, forward-looking IT services.

What you’ll do

• Design and build AI-powered internal platforms and automation frameworks that connect systems, enable self-service, and scale IT capabilities — incorporating agent-based workflows, event-driven integrations, and intelligent orchestration across the infrastructure stack
• Own and evolve core IT systems (Okta, Google Workspace, Atlassian, Slack, Fleet, Linear, Sentinel One, Palo Alto Networks, AWS and more) as a cohesive, integrated platform — building automations and integrations that connect these systems rather than managing them in isolation
• Define and implement how AI and automation interact with internal infrastructure — including agentic workflows, system-to-system orchestration, and AI-enabled processes that reduce manual effort and improve how work gets done at scale
• Partner cross-functionally with engineers, leaders, and business teams to define systems architecture, automation strategy, and AI-enabled workflows — driving execution, influencing technical direction, and mentoring teammates

Lead IT technical initiatives end-to-end — from design and stakeholder alignment through delivery and ongoing operations, along with managing vendor relationships, evaluating tools, and driving long-term architectural decisions

• Ensure security, compliance, and operational reliability across the infrastructure stack — including identity access controls, least-privilege design, system health monitoring, and scalable operational practices

In order to be successful, you must bring

• 5+ years of experience in IT systems engineering, infrastructure, or platform engineering in a distributed enterprise environment with a demonstrated track record of owning systems end-to-end, shaping technical direction, and driving cross-functional outcomes
• Deep, hands-on expertise designing and building automation and integration frameworks — Okta Workflows in production is required along with experience in tools like AWS Lambda, Workato, Jira Automations, Slack Workflows, or equivalent platforms
• Strong understanding of identity and access management systems and protocols (SAML, SCIM, OAuth2.0/OIDC, LDAP), with the ability to design scalable, secure IAM architectures across SaaS, cloud, and enterprise environments
• Applied AI and automation experience — a demonstrated track record of building AI-enabled workflows, agent-based patterns, or intelligent orchestration that reduces manual effort and improves system operations, not just familiarity with the concepts
• Scripting or programming fluency (Python, JavaScript, Shell, or equivalent) and working knowledge of AWS or other cloud platforms for building scalable, reliable automations and integrations
• Strong systems thinking, communication, and cross-functional influence — with the ability to navigate ambiguity, partner across teams, mentor others, and ensure security, compliance, and governance are embedded in every system you own

Expected salary ranges

• For candidates living in San Francisco / Bay Area, San Jose, New York City, or Seattle metros, the expected salary range for the role is currently $178,500 to $231,000.
• For candidates living in Austin, TX or Washington DC metros or in California, Massachusetts, New Jersey, or Washington states, the expected salary range for the role is currently $160,700 to $207,900.
• For candidates living in all other US locations, the expected salary range for this role is currently $152,200 to $196,900.

About the IT Infrastructure Team

The IT Infrastructure team builds and operates the systems that power how Thumbtack employees work. The team is composed of two core functions — IT Systems & Endpoint Engineering and IT Systems Architecture — delivering reliable, scalable, and secure infrastructure across identity, SaaS platforms, cloud systems, and endpoint management. We partner closely with IT Operations, Security, and other Engineering teams to provide seamless access to the tools employees need, and we own these systems end-to-end — from intake and implementation through ongoing operations and continuous improvement.