Senior Lead Systems Engineer (AI & Automation)

Location: Chicago, United States

Salary: $111,000–$174,000 per year, plus potential bonus or commission and equity.

Company

hirify.global is a customer engagement SaaS platform that helps brands deliver personalized, cross-channel customer experiences using composable intelligence and AI.

What you will do

• Design and build intelligent automation across enterprise platforms to reduce manual effort and improve employee productivity.
• Develop scalable integrations, APIs, middleware, and event-driven workflows connecting Slack, Okta, Workday, Atlassian, GitHub, Google Workspace, and other SaaS applications.
• Build conversational IT and self-service experiences that reduce reliance on ticket-based workflows.
• Design resilient enterprise platform architectures with strong maintainability, extensibility, reliability, and operational maturity.
• Evaluate and implement AI technologies, large language models, MCP integrations, and agent frameworks.
• Provide technical leadership, contribute to long-term platform strategy, and mentor engineers.

Requirements

• 8+ years of experience designing enterprise-scale integrations and automation across modern SaaS environments.
• Strong software engineering experience building APIs, integrations, automation, or platform services.
• Proficiency in Python, Go, TypeScript, or JavaScript.
• Experience with REST APIs, webhooks, OAuth, SCIM, GraphQL, and modern authentication standards.
• Experience with enterprise platforms such as Okta, Workday, Slack, Atlassian, GitHub, or Google Workspace.
• Ability to design scalable architectures and collaborate with engineering, security, infrastructure, and business teams.

Nice to have

• Experience implementing AI agents, MCP integrations, LLM-powered workflows, or enterprise AI platforms.
• Experience with Terraform, infrastructure as code, cloud automation, event-driven architectures, message queues, or serverless technologies.
• Experience with AWS, GCP, Azure, internal developer platforms, or enterprise integration frameworks.
• Experience supporting high-growth SaaS organizations.

Culture & Benefits

• Hybrid ways of working with a curated in-office experience.
• Equity, retirement and employee stock purchase plans, and flexible paid time off.
• Medical, dental, vision, life, disability, fertility, and equal paid parental leave benefits, varying by location.
• Professional development through career pathing, learning platforms, and a yearly learning stipend.
• Employee Resource Groups, community volunteering, donation matching, and a collaborative culture.

Hiring process

• AI-assisted tools may analyze application materials and support interview scheduling, recording, and note summarization.
• Recruiting teams remain responsible for hiring decisions; candidates may have rights to request manual review or opt out depending on location.