Staff IT Engineer

Ironclad; Chicago (IL); On-site; USD 160,000 - 185,000; Full time

Benefits offered by this job

Health coverage (medical, dental, and

Dental coverage

Vision coverage

Parental leave

401(k) with employer match

Job summary

Ironclad is seeking a Staff Systems Engineer, Automations & Integrations to lead enterprise-wide automations, AI-assisted workflows, and governed data integrations across Ironclad’s tech stack. You will partner with Biz Tech and GTM/EPD/G&A teams to build observable automation frameworks and scalable patterns.

You will design resilient architectures, mentor automation engineers, and drive governance, reliability, and rapid delivery for cross-functional projects that accelerate business velocity.

Qualifications

• 5+ years in automation, integration, or data engineering roles owning complex systems.
• Strong Workato design, API integrations, and error handling practices.
• Experience with Glean or similar AI knowledge platforms integrated into processes.
• Familiarity with Salesforce, NetSuite, BambooHR, and identity platforms.
• Proficient in ETL/ELT, data modeling, and at least one scripting language.

Responsibilities

• Design and build robust automations and integrations across business systems with focus on reliability and observability.
• Lead cross-functional integration projects end-to-end for GTM, EPD, and G&A stakeholders.
• Operationalize AI-powered workflows by integrating AI tools into systems in a governed way.
• Establish standards for automation design, testing, monitoring, and security; drive adoption of patterns.
• Implement strong error handling, runbooks, routing, and remediation to minimize user impact.
• Model and promote engineering best practices in Workato and related stacks.
• Translate business problems into technical designs and roadmaps; balance quick wins with scalable architecture.
• Mentor automation engineers and analysts; lead design reviews and enablement sessions.
• Continuously explore innovations in automation patterns and AI agentic capabilities with governance.

Skills

Automation design

System architecture

Stakeholder engagement

Mentoring“

Tools

Workato

Glean

Salesforce

NetSuite

Okta

Job description

Ironclad is the leading AI contracting platform that transforms agreements into assets. Contracts move faster, insights surface instantly, and agents push work forward, all with you in control. Whether you’re buying or selling, Ironclad unifies the entire process on one intelligent platform, providing leaders with the visibility they need to stay one step ahead. That’s why the world’s most transformative organizations, from Rivian to the World Health Organization and the Associated Press, trust Ironclad to accelerate their business. We’re consistently recognized as a leader in the industry: a Leader in the Forrester Wave and Gartner Magic Quadrant for Contract Lifecycle Management, a Fortune Great Place to Work, and one of Fast Company’s Most Innovative Workplaces. Ironclad has also been named to Forbes’ AI 50 and Business Insider’s list of Companies to Bet Your Career On. We’re backed by leading investors including Accel, Y Combinator, Sequoia, BOND, and Franklin Templeton. For more information, visit www.ironcladapp.com or follow us on LinkedIn.

About The Role

As a Staff Systems Engineer, Automations & Integrations, you will be a hands-on technical leader designing and delivering enterprise-wide automations, AI-assisted workflows, and governed data integrations across Ironclad’s business technology landscape. You’ll work across Biz Tech and partner teams (GTM, EPD, G&A, and more) to build resilient, observable automation frameworks and integrations that materially improve employee and customer experiences and business velocity. You’ll combine deep technical expertise in tools like Workato, Glean, and our core SaaS/identity stack with strong systems thinking to create reusable patterns, robust error handling, and governed data flows that scale safely and reliably. This is an individual contributor role with broad scope and influence: you will partner closely with stakeholders and engineering peers, mentor other automation engineers, and set technical direction for high-impact initiatives in automations, integrations, and AI.

What you’ll do:

• Design and build robust automations and integrations across our business systems (e.g., Salesforce, NetSuite, BambooHR, identity, engineering and ticketing tools), with a focus on reliability, observability, and reusability in Workato and adjacent platforms.
• Lead complex, cross-functional integration projects end-to-end: requirements, solution design, implementation, testing, deployment, and hyper-care for GTM, EPD, and G&A stakeholders.
• Operationalize AI-powered workflows and agents (e.g., knowledge retrieval, intelligent triage, automated approvals, autonomous and prompted user workflows) by integrating Glean and other AI tools into systems and processes in a governed way.
• Establish and evolve standards for automation design, testing, monitoring/observability, documentation, and security/compliance; drive adoption of shared patterns, components, and best practices across Biz Tech and partner teams.
• Implement best-in-class error handling and alerting for automations, including clear runbooks, routing, and remediation patterns to minimize impact on end users and business operations.
• Model and champion high-quality engineering practices in Workato and related stacks (version control, peer reviews, CI/CD for recipes, configuration-as-code where appropriate).
• Partner with stakeholders and executives to translate business problems into technical designs and roadmaps, balancing quick wins with scalable architectures and measurable outcomes.
• Mentor and uplevel other engineers and analysts through design reviews, pairing, documentation, and internal enablement sessions, helping grow our automation and AI capabilities across the company.
• Continuously explore and introduce innovation in automation patterns, AI agentic capabilities, and integration approaches while maintaining appropriate governance and reliability.

What we’re looking for:

• 5+ years of experience in automation, integration, or data engineering roles, with a strong track record of owning and delivering complex, business-critical systems (preferably in SaaS/B2B environments).
• Expertise with Workato as a primary automation platform, including recipe design, API integrations, SDK/custom connectors, error handling, and operational best practices; Workato Automation Pro certification is a plus.
• Hands-on experience with Glean (or similar AI knowledge platforms), including administration, API usage, and integrating AI retrieval/agentic workflows into business processes.
• Deep familiarity with core enterprise systems, such as Salesforce, NetSuite, BambooHR, Okta/identity, and engineering/ticketing systems, and how data and processes flow across them.
• Strong architectural and automation design skills, able to define patterns, reference architectures, and reusable components for integrations and workflows.
• Solid background in ETL/ELT, data modeling, and SQL/T-SQL, plus proficiency in at least one scripting or programming language (e.g., Python, Ruby, or similar) to build integrations, utilities, and tooling as needed.
• Proven experience operationalizing automation workflows and AI models for enterprise use cases, including monitoring, observability, governance, and lifecycle management.
• Excellent stakeholder engagement and communication skills, with the ability to translate business problems into technical designs and to articulate trade-offs and recommendations clearly to both technical and non-technical audiences.
• Comfortable leading by influence: driving standards, guiding solution design, and mentoring peers without direct people management responsibilities.

Base Salary Range

$160,000 - $185,000

+Bonus + Equity

The base salary range represents the minimum and maximum of the salary range for this position based at our San Francisco headquarters. The actual base salary offered for this position will depend on numerous factors, including individual proficiency, anticipated performance, and the location of the selected candidate. Our base salary is just one component of Ironclad’s competitive total rewards package, which also includes equity awards (a new hire grant, along with opportunities for additional awards throughout your tenure), competitive health and wellness benefits, and a commitment to career growth and development.

US Full-Time Employee Benefits at Ironclad

• 100% health coverage for employees (medical, dental, and vision), and 75% coverage for dependents with buy-up plan options available
• Market-leading leave policies, including gender-neutral parental leave and compassionate leave
• Family forming support through Maven for you and your partner
• Paid time off - take the time you need, when you need it
• Monthly stipends for wellbeing, hybrid work, and (if applicable) cell phone use
• Mental health support through Modern Health, including therapy, coaching, and digital tools
• Pre-tax commuter benefits (US Employees)
• 401(k) plan with Fidelity with employer match (US Employees)
• Regular team events to connect, recharge, and have fun
• And most importantly: the opportunity to help build the company you want to work at
• UK Employee-specific benefits are included on our UK job postings

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.

Compensation Range: $160K - $185K