Senior Lead Systems Engineer, AI & Automation

United States Digital Space LLC; Chicago (IL); On-site; USD 111,000 - 174,000; Full time

Job summary

United States Digital Space LLC is seeking a Senior Lead Systems Engineer to architect scalable enterprise integrations and automation across major SaaS platforms. You will drive AI-enabled workflows, develop APIs, and build resilient, scalable solutions that improve employee experience.

The role emphasizes collaboration with Security, Infrastructure, Product, and IT teams, while advancing the company’s strategic direction in automation, integration, and AI-powered tech.

Qualifications

• 8+ years of experience designing enterprise-scale integrations and automation across modern SaaS environments.
• Strong software engineering background with experience building APIs, integrations, automation, or platform services.
• Proficient in one or more programming languages such as Python, Go, TypeScript, or JavaScript.
• Experienced working with REST APIs, webhooks, OAuth, SCIM, GraphQL, and modern authentication standards.
• Familiar with enterprise platforms such as Okta, Workday, Slack, Atlassian, GitHub, Google Workspace, or similar SaaS ecosystems.

Responsibilities

• Architect scalable integrations across SaaS platforms and automate enterprise workflows.
• Lead complex technical initiatives from concept through delivery.
• Build integrations spanning Slack, Okta, Workday, Atlassian, GitHub, Google Workspace, and other systems.
• Collaborate with Security, Infrastructure, Product, and IT teams to deliver reliable solutions.
• Shape long-term strategy around enterprise integrations, intelligent workflows, and AI-enabled experiences.
• Develop reusable automation frameworks and internal tooling to improve delivery speed and maintainability.
• Partner with Security, Compliance, and Infrastructure to ensure governance and operational maturity.

Skills

Enterprise integration

Automation

APIs

Programming (Python/Go/JS)

Tools

Terraform

Cloud automation tooling

Job description

At the company, we have found our people. We’re a genuinely approachable, exceptionally kind, and intensely passionate crew.

We seek to ignite that passion by setting high standards, championing teamwork, and creating work-life harmony as we collectively navigate rapid growth on a global scale while striving for greater equity and opportunity – inside and outside our organization.

To flourish here, you must be prepared to set a high bar for yourself and those around you. There is always a way to contribute: Acting with autonomy, having accountability and being open to new perspectives are essential to our continued success.

Our deep curiosity to learn and our eagerness to share diverse passions with others gives us balance and injects a one-of-a-kind vibrancy into our culture.

If you are driven to solve exhilarating challenges and have a bias toward action in the face of change, you will be empowered to make a real impact here, with a sharp and passionate team at your back. If the company sounds like a place where you can thrive, we can’t wait to meet you.

WHAT YOU'LL DO

We're looking for a Senior Lead Systems Engineer who's passionate about building the next generation of enterprise technology through automation, software engineering, AI, and intelligent integrations. In this role, you'll architect scalable solutions that connect the systems powering the company while helping redefine how employees interact with IT through conversational experiences, automation, and self-service.

You'll lead complex technical initiatives from concept through delivery, building integrations that span platforms such as Slack, Okta, Workday, Atlassian, GitHub, Google Workspace, and other critical business systems. You'll partner closely with Security, Infrastructure, Product, and IT teams to build reliable, scalable solutions that reduce operational overhead and improve the employee experience.

This role goes beyond traditional system engineering. We're looking for someone who enjoys solving business problems through software, APIs, automation, and AI. You'll help shape our long-term strategy around enterprise integrations, intelligent workflows, and agentic experiences that enable employees to get work done faster and more intuitively.

You'll be part of a team that values reliability, resiliency, scalability, extensibility, and thoughtful engineering. We operate with a shared sense of ownership, continuously look for opportunities to automate manual work, and embrace emerging technologies that allow us to scale efficiently while delivering exceptional internal experiences.

If you enjoy designing enterprise architecture, building integrations, and leveraging AI to modernize how organizations operate, we'd love to meet you.

You'll lead initiatives that shape the future of enterprise technology at the company, including:

• Enterprise Automation & AI:

• Design and build intelligent automation that streamlines business processes across enterprise platforms. Leverage AI, agentic workflows, and modern integration patterns to reduce manual effort, improve operational efficiency, and enhance employee productivity

• Enterprise Integrations:

• Design and develop scalable integrations across platforms including Slack, Okta, Workday, Atlassian, GitHub, Google Workspace, and other SaaS applications. Build APIs, middleware, and event-driven workflows that create seamless employee experiences

• Conversational IT & Self-Service:

• Help evolve how employees interact with IT by building conversational interfaces and self-service experiences that reduce reliance on traditional ticket-based workflows while improving service delivery and employee satisfaction

• Enterprise Platform Architecture:

• Design scalable, resilient solutions that improve how enterprise platforms communicate and operate together. Evaluate architecture decisions with long-term maintainability, extensibility, and operational excellence in mind

• AI Platform Enablement:

• Evaluate, pilot, and implement emerging AI technologies, large language models, MCP integrations, and agent frameworks that enable intelligent automation across enterprise systems while establishing best practices for responsible adoption

• Automation & Developer Experience:

• Build reusable automation frameworks, integration services, and internal tooling that accelerate delivery, reduce operational toil, and improve the maintainability of enterprise platforms

• Governance & Operational Excellence:

• Partner with Security, Compliance, and Infrastructure teams to ensure enterprise solutions meet governance requirements while maintaining simplicity, scalability, and operational maturity. Document architecture, implementation decisions, and operational processes following governance and compliance standards

• Innovation & Emerging Technology:

• Continuously research emerging technologies, integration capabilities, and AI advancements that can improve scalability, reduce operational complexity, and create new opportunities for automation

• Strategy & Technical Leadership:

• Contribute to enterprise platform strategy and long-term technical roadmaps. Provide technical leadership on complex initiatives while mentoring engineers on automation, integration, and software engineering best practices

WHO YOU ARE

• 8+ years of experience designing enterprise-scale integrations and automation across modern SaaS environments

• Strong software engineering background with experience building APIs, integrations, automation, or platform services

• Proficient in one or more programming languages such as Python, Go, TypeScript, or JavaScript

• Experienced working with REST APIs, webhooks, OAuth, SCIM, GraphQL, and modern authentication standards

• Familiar with enterprise platforms such as Okta, Workday, Slack, Atlassian, GitHub, Google Workspace, or similar SaaS ecosystems

• Skilled in designing scalable architectures that balance business requirements, security, and operational simplicity

• Experienced collaborating across engineering, security, infrastructure, and business teams to deliver impactful technical solutions

• Passionate about leveraging AI, automation, and software engineering to solve operational challenges

• Curious, collaborative, and motivated by continuous improvement and thoughtful systems design

Bonus:

• Experience implementing AI agents, MCP integrations, LLM-powered workflows, or enterprise AI platforms

• Experience with Terraform, Infrastructure as Code, or cloud automation tooling

• Experience with event-driven architectures, message queues, or serverless technologies

• Experience integrating Workday, Okta, Atlassian Cloud, Slack Platform, GitHub Enterprise, or Google Workspace APIs

• Familiarity with cloud platforms such as AWS, GCP, or Azure

• Experience building internal developer platforms or enterprise integration frameworks

• Experience supporting high-growth SaaS organizations with complex enterprise technology environments

For candidates based in the United States, the pay range for this position at the start of employment is expected to be between $111,000 and $174,000/year with an expected On Target Earnings (OTE) between $123,000 and $193,000/year (including bonus or commission). Your exact offer may vary depending on multiple individualized factors, including market location, job-related knowledge, skills, and experience. In addition to cash compensation, this role qualifi