Senior GTM Systems & AI Engineer - Cobalt

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.

Description

We are looking for a Senior GTM Systems & AI Engineer to own and scale the technology infrastructure that powers Cobalt’s go-to-market organization.

Reporting to the Sr. Director of Revenue Operations, this role will serve as the technical owner of our GTM technology ecosystem, with deep hands-on responsibility for Salesforce, HubSpot, integrations, enrichment, automation, and the systems supporting our customer lifecycle.

What You'll Own

GTM Systems & Architecture

• Serve as the primary technical owner and administrator of Salesforce, including architecture, objects, Flows, automation, permissions, integrations, data model, release management, reporting infrastructure, and system governance.
• Own the broader GTM technology ecosystem, including integrations and data flows between Salesforce, HubSpot, Customer Success platforms, enrichment providers, prospecting and sequencing tools, and other GTM applications.
• Partner closely with Revenue Operations to translate GTM strategy and business requirements into scalable technical solutions across Marketing, Sales, and Customer Success.
• Evaluate, implement, and optimize GTM technologies with a focus on business impact, scalability, usability, and reducing operational complexity.

HubSpot & Marketing Technology

• Serve as the primary technical owner and administrator of HubSpot, including workflows, lifecycle stages, lead scoring and routing, forms, campaign infrastructure, attribution configuration, integrations, automation, and data synchronization with Salesforce.
• Partner with Marketing and Revenue Operations to ensure our marketing technology infrastructure supports lead management, campaign execution, attribution, intent signals, funnel measurement, and Marketing-to-Sales handoffs.
• Maintain alignment between Salesforce and HubSpot data models, lifecycle definitions, routing logic, campaign data, and reporting requirements.

Data, Enrichment & GTM Signals

• Own the technical infrastructure supporting GTM data quality and enrichment, including enrichment providers, field mapping, matching logic, deduplication, normalization, data governance, and ongoing monitoring.
• Design and maintain reliable enrichment and data orchestration workflows that ensure GTM teams have accurate, complete, and actionable account and contact data.
• Build scalable processes for activating intent signals, engagement data, enrichment signals, and buying triggers across GTM systems.
• Proactively monitor data and integration health, identify gaps or failures, and implement solutions that improve data accuracy, coverage, reliability, and usability.

Customer Success Technology

• Support the administration and integration of Customer Success platforms and the data infrastructure supporting the post-sale customer lifecycle.
• Partner with Revenue Operations and Customer Success to enable processes such as customer health scoring, segmentation, account planning, renewals, expansion, churn risk, and lifecycle management.
• Ensure customer and commercial data flows reliably across Salesforce, Customer Success platforms, and the broader GTM ecosystem.

Automation, AI & Innovation

• Identify, design, and implement opportunities to automate repetitive GTM workflows across Marketing, Sales, Customer Success, and Revenue Operations.
• Build scalable workflow automation using native platform capabilities, APIs, webhooks, and tools such as n8n, Zapier, or similar technologies.
• Evaluate and implement practical AI-powered solutions that improve GTM productivity, research, data quality, prioritization, customer insights, or operational efficiency.
• Build and experiment with AI-enabled workflows and agents where they can deliver measurable business value.
• Stay current on emerging GTM and AI technologies and proactively recommend opportunities to improve how our revenue organization operates.

Systems Governance & Operational Excellence

• Own system health, integrations, permissions, release management, documentation, and technical governance across the GTM technology ecosystem.
• Establish monitoring and controls to proactively identify integration failures, data issues, workflow errors, and system risks.
• Maintain clear documentation of architecture, integrations, workflows, business rules, and system dependencies to support scalability and business continuity.
• Own technical initiatives end-to-end, from discovery and solution design through implementation, testing, deployment, and ongoing optimization.

You Must Have

• 7+ years of experience in GTM Systems, Revenue Operations, Marketing Operations, Salesforce Administration, GTM Engineering, or a related field within B2B SaaS.
• Advanced hands-on Salesforce administration expertise, including Flows, automation, permissions, integrations, data architecture, reporting, dashboards, and governance.
• Advanced hands-on HubSpot administration expertise, including workflows, lifecycle management, lead scoring and routing, forms, campaigns, attribution, automation, integrations, and reporting.
• Experience serving as a primary technical owner of Salesforce and HubSpot, including managing the integration and data flow between the two platforms.
• Strong understanding of the end-to-end B2B SaaS GTM lifecycle across Marketing, Sales, and Customer Success.
• Experience with GTM data enrichment and governance.
• Experience designing and maintaining cross-platform integrations using APIs, webhooks, middleware, or workflow automation platforms.
• Experience administering or integrating Customer Success platforms and supporting post-sale customer data and workflows.
• Experience applying AI and automation to GTM workflows.

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
• Benefit from medical, dental, vision and life insurance
• Leverage stipends for wellness, work-from-home equipment & wifi, and learning & development
• Flexible, generous paid time off and paid parental leave