Head of GTM Systems & AI

<h3><strong>Introduction to the Team &amp; Role</strong></h3> <div>&nbsp;</div> <div>What if your team was the one that got to build the future of how a company runs — and tried it on itself first?</div> <div>&nbsp;</div> <div>GTM Systems owns the tech stack behind 360Learning's commercial engine — Salesforce, Marketo, data enrichment and AI tooling across sales, marketing, customer success and services. Our mission is to be a force multiplier for the business: making go-to-market faster, smarter and more effective.</div> <div>&nbsp;</div> <div>We already have a high-performing team, mature systems, extensive documentation, and an ambitious AI vision. Now we need someone to build on that foundation and take it to the next level.</div> <div>&nbsp;</div> <div>You'll work closely with GTM leaders, operators, data teams and engineering to turn ambiguous business problems into reliable, scalable products. You'll partner with each team to define the target state — where AI can take work off their plate, and where the human touch matters — then build the systems and agents that get them there.</div> <div>&nbsp;</div> <div>This is a high-impact role for someone who loves working at the intersection of product, systems, AI and go-to-market strategy.</div> <div>&nbsp;</div> <h3><strong>Key Responsibility Areas</strong></h3> <div> <ul> <li>Own the internal AI operating model for GTM — the library of skills, agent evals, cost, adoption and ROI — in partnership with Data and Enablement.</li> <li>Keep the team a step ahead as customer zero for AI, turning what works into patterns other functions adopt.</li> <li>Own the long-term design of the GTM stack — CRM, marketing automation, CS tooling — deciding what to build vs. buy.</li> <li>Help the company prioritize by identifying the best solution to each business problem and sizing its cost and feasibility.</li> <li>Lead and coach five senior ICs across Salesforce, marketing/BDR, CS systems and web ops. Set a high bar for documentation, testing and deployment — and hold it without slowing the team down.</li> <li>Run vendor management end to end: evaluations, the quarterly keep-or-kill review, and renewals.</li> <li>Partner as a peer to the leaders of Data, Enablement, Security, Finance and every commercial function.</li> <li>Drive adoption and change management for new GTM capabilities across distributed teams.</li> </ul> </div><br><strong>What You'll Do</strong><br><div><strong>Within 1 month, you will:</strong> <li>Know the team, the stack, and the cross-functional leaders and teams you’ll partner with</li> <li>Understand the main business challenges and opportunities for each GTM function</li> <li>Own the team's current quarterly objectives and the routines that keep them visible.</li> <br><strong>Within 3 months, you will:</strong> <li>Have taken one major cross-functional change from plan to done</li> <li>Own the full vendor-renewal cycle across the commercial stack</li> <li>Have co-written the next quarter's objectives with the performance and enablement teams, each one stating the business problem, the current state, the expected impact and the plan.</li> <br><strong>Within 6 months, you will:</strong> <li>Have co-written the next quarter's objectives with the performance and enablement teams, each one stating the business problem, the current state, the expected impact and the plan.</li> <li>Have shipped at least one AI agent that watches business data and reaches people on its own, with a named business owner and outcome measures agreed before launch.</li> <li>Have a 12-18 month roadmap, setting the high-level vision across our systems infrastructure, ways of working, and AI portfolio</li> <br><strong>Within 12 months, you will:</strong> <li>Show, in numbers, the capacity the commercial organization reinvested because of what the team built.</li> <li>Have a development path agreed with each member of the team.</li> <li>Have the team recognized as the company's reference for AI-native operations</li> </div><br><strong>The Skill Set</strong><br><div> <li>5+ years across GTM systems, agentic/AI workflow products, revenue technology, enterprise SaaS — or an adjacent path like technical product management or consulting where you designed and shipped real systems with a strong AI mandate.&nbsp;</li> <li>Turn ambiguous business problems into reliable, scalable tooling — you read a process, tell whether it's any good, spot where AI creates value, and judge when to automate (and when not to), across the full revenue engine.</li> <li>Have fluency in modern GTM systems: Salesforce, marketing automation, enrichment, routing, attribution, lead-to-quote, billing or customer lifecycle tools. Deep Salesforce fluency is a strong plus.</li> <li>Have built with modern AI tooling: agents, plugins or skills on top of LLMs, connectors to business systems, and evals that tell you whether an agent is good.</li> <li>You define KPIs, run experiments, and use data to prioritize wher