Senior GTM Systems & AI Specialist

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 500 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 & AI Specialist 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. This is a highly cross-functional individual contributor role for someone who combines deep GTM systems expertise with a strong understanding of how modern B2B SaaS revenue organizations operate. You won’t just administer tools — you’ll partner with Revenue Operations, Marketing, Sales, Customer Success, and Analytics to translate business needs into scalable technical solutions and identify opportunities to leverage automation and AI to improve how our GTM teams operate. Success in this role means our GTM teams have reliable systems, connected and trustworthy data, scalable automation, and an increasingly AI-enabled technology ecosystem that helps the business operate more efficiently. 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, with the ability to understand business requirements and translate them into scalable technical solutions. • Strong experience with GTM data enrichment and governance, including enrichment providers, matching and mapping logic, deduplication, normalization, data quality monitoring, and CRM data management. • Experience designing and maintaining cross-platform integrations using APIs, webhooks, middleware, or workflow automation platforms. • Experience building scalable workflow automation using native GTM platforms and tools such as n8n, Zapier, Make, or similar technologies. • Experience administering or integrating Customer Success platforms and supporting post-sale customer data and workflows. • Experience applying AI and automation to GTM workflows, with an understanding of where AI can create meaningful business value and where traditional automation is the better solution. • Demonstrated ability to independently own business-critical GTM systems, troubleshoot complex issues, and drive technical initiatives from requirements through deployment. • Strong communication and partnership skills, with the ability to work effectively with Revenue Operations, Marketing, Sales, Customer Success, Analytics, and technical and non-technical stakeholders. Nice to Have • Experience with GTM technologies such as Apollo, Clay, LeanData, ZoomInfo, 6sense, Gong, Outreach, Qualified, Clari, UserGems, Planhat, or similar platforms. • Experience designing signal-based GTM workflows using intent, engagement, enrichment, product, or customer data. • Experience building or deploying AI-powered workflows or agents within GTM systems. • Working knowledge of SQL, Python, JavaScript, TypeScript, or similar technologies used to extend and automate GTM systems. • Experience supporting a scaling SaaS organization through systems transformation, technology consolidation, or process redesign. 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 (