Automation Engineer Jobs in Chicago, IL

Who We Are

Cobalt was founded on the belief of a fundamental human aspiration: the desire to live better and safer. It all started in 2013, when our founders realized that pentesting can be better. Today our diverse, fully remote team is committed to helping organizations of all sizes with seamless, effective and collaborative Offensive Security Testing that empower organizations to OPERATE FEARLESSLY and INNOVATE SECURELY.

Our customers can start a pentest in as little as 24 hours and integrate with advanced development cycles thanks to the powerful combination of our SaaS platform coupled with an exclusive community of testers known as the Cobalt Core. Accepting just 5% of applicants, the Cobalt Core boasts over 400 closely vetted and highly skilled testers who jointly conduct thousands of tests each year and are at the forefront of identifying and helping remediate risk across a dynamically changing attack surface.

Cobalt is an Equal Opportunity Employer and we strive to build a diverse and inclusive workforce at our company. At Cobalt we aspire to engage with diverse individuals, communities, and organizations in order to continue to nurture our unique rich diverse culture. Join our team, and be your true self to do your best work.

Description

We are looking for a Senior GTM Systems & Automation Engineer to build and own the technical infrastructure that powers our revenue engine. This role reports to the Sr. Director of Revenue Operations and partners closely with Sales, Marketing, Customer Success, and Revenue Operations leaders to scale our go-to-market organization.

As a Senior GTM Systems & Automation Engineer, you will own the systems, automations, integrations, and data foundations that enable our teams to operate more efficiently and make better decisions. You will architect scalable solutions across Salesforce, HubSpot, AI-powered workflows, and the broader GTM technology stack while ensuring the business has clean data, reliable systems, and streamlined processes.

This is a highly visible, high-impact individual contributor role for someone who combines strong technical expertise with sound business judgment and enjoys building solutions that create measurable business impact.

What Success Looks Like

Within your first 12 months, you will modernize and scale our GTM infrastructure, improve data quality and system reliability, increase automation across the revenue organization, reduce operational bottlenecks, and help establish a more AI-native operating model that enables our teams to move faster and operate more efficiently.

What You'll Own

GTM Systems & Architecture

• Own the design, administration, scalability, and reliability of the GTM technology stack, including Salesforce, HubSpot, customer success platforms, enrichment providers, sequencing tools, AI solutions, and workflow automation platforms.
• Serve as the primary technical owner for integrations, APIs, webhooks, system health, data governance, security permissions, release management, documentation, and operational continuity.
• Design and optimize scalable revenue processes across the customer lifecycle, including lead management, pipeline progression, customer onboarding, renewals, expansion, lead routing, lifecycle management, attribution, and customer data architecture.
• Evaluate, implement, and optimize GTM technologies that create measurable business impact while reducing operational complexity.
• Create and maintain documentation for systems, workflows, integrations, business rules, and operational processes to ensure scalability and business continuity.

AI, Automation & Operational Scale

• Design, build, and deploy AI-powered workflows, agents, and automations that eliminate manual work across Sales, Marketing, Customer Success, and Revenue Operations.
• Build AI-driven solutions that automate seller research, account prioritization, CRM updates, meeting follow-up, lead routing, customer engagement, and outbound prospecting.
• Develop signal-based workflows using intent data, enrichment signals, buying triggers, customer engagement data, and AI-powered insights.
• Evaluate emerging AI technologies and identify practical applications that improve productivity, scalability, and business outcomes.
• Continuously identify opportunities to redesign processes using AI and automation so teams can focus on higher-value work.
• Help establish AI best practices, governance, and adoption across the go-to-market organization.

Data Infrastructure & Governance

• Own data quality from source to activation, ensuring records remain clean, enriched, deduplicated, and trustworthy.
• Design enrichment strategies, identity resolution frameworks, and governance processes that improve data accuracy and coverage.
• Build and maintain the data infrastructure required to support automation, reporting, forecasting, and operational workflows.
• Partner with stakeholders to ensure data is structured, accessible, and reliable for decision-making.
• Run automated audits, enrichment workflows, and monitoring processes to maintain ongoing data integrity.

Cross-Functional Leadership

• Partner closely with Sales, Marketing, Customer Success, Finance, and Revenue Operations leaders to improve execution, visibility, and operational efficiency across the customer lifecycle.
• Translate business requirements into scalable technical solutions and rapidly prototype and deploy improvements.
• Act as the internal expert on GTM systems, automation, AI, and operational best practices.
• Own projects end-to-end from discovery and design through implementation, adoption, and continuous optimization.

You Must Have

• 7+ years of experience in Revenue Operations, GTM Systems, Sales Operations, Marketing Operations, GTM Engineering, or a related field.
• Advanced hands-on Salesforce administration experience is required, including Flows, automation, permissions, integrations, reporting, dashboards, and data architecture.
• Advanced hands-on HubSpot administration experience is required, including workflows, lifecycle management, lead routing, forms, attribution, automation, integrations, and reporting.
• Experience serving as a primary owner of both Salesforce and HubSpot in a scaling B2B SaaS environment.
• Demonstrated experience building automated workflows using tools such as Zapier, n8n, Python, SQL or similar technologies.
• Demonstrated experience designing, building, and deploying production-ready AI workflows, agents, or automations that delivered measurable business outcomes.
• Experience designing and managing complex system integrations using APIs, webhooks, middleware, and automation platforms.
• Strong understanding of the B2B customer lifecycle, including pipeline generation, lead management, customer onboarding, expansion, and renewals.
• Experience with data enrichment, identity resolution, deduplication, and CRM data governance.
• Demonstrated ability to independently own business-critical systems, manage competing priorities, and drive initiatives from concept through execution.
• Strong communication skills and the ability to partner effectively with both technical and non-technical stakeholders.

Nice to Have

• Experience in a high-growth SaaS, AI, or technology company.
• Familiarity with tools such as Clay, LeanData, Apollo, ZoomInfo, Gong, Outreach, Qualified, Clari, UserGems, Common Room, Planhat, or similar GTM technologies.
• Experience supporting customer success operations, renewal processes, and customer lifecycle management.
• Proficiency in Python, SQL, TypeScript, or similar technologies used to extend and automate GTM systems.
• Strong builder mentality with a passion for automation, experimentation, continuous improvement, and operational excellence.

Why You Should Join Us

• Grow in a passionate, rapidly expanding industry operating at the forefront of the Pentesting industry
• Work directly with experienced senior leaders with ongoing mentorship opportunities
• Earn competitive compensation and an attractive equity plan
• Save for the future with a 401(k) program (US) or pension (EU)
• Benefit from medical, dental, vision and life insurance (US) or statutory healthcare (EU)
• Leverage stipends for:
• • Wellness
  • Work-from-home equipment & wifi
  • Learning & development
• Make the most of our flexible, generous paid time off and paid parental leave

Pay Range Disclosure (For US openings only)

Cobalt is committed to fair and equitable compensation practices. The salary range for this role is ($135,000 - $160,000) + equity + benefits. A candidate's salary is determined by various factors including, but not limited to, relevant work experience, skills, and certifications. The salary range may differ in other states and may be impacted by proximity to major metropolitan cities.

Cobalt (the "Company") is an equal opportunity employer, and we want the best available persons for every job. The Company makes employment decisions only based on merit. It is the Company's policy to prohibit discrimination in any employment opportunity (including but not limited to recruitment, employment, promotion, salary increases, benefits, termination and all other terms and conditions of employment) based on race, color, sex, sexual orientation, gender, gender identity, gender expression, genetic information, pregnancy, religious creed, national origin, ancestry, age, physical/mental disability, medical condition, marital/domestic partner status, military and veteran status, height, weight or any other such characteristic protected by federal, state or local law. The Company is committed to complying with all applicable laws and providing equal employment opportunities. This commitment applies to all persons involved in the operations of the Company regardless of where the employee is located and prohibits unlawful discrimination by any employee of the Company.

Cobalt is an E-Verify employer. E-Verify is an Internet-based system operated by the Department of Homeland Security (DHS) in partnership with the Social Security Administration (SSA). It allows participating employers to electronically verify the employment eligibility of their newly hired employees in the United States.