Head of GTM Systems & AI

Introduction to the Team & Role

What if your team was the one that got to build the future of how a company runs — and tried it on itself first?

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.

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.

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.

This is a high-impact role for someone who loves working at the intersection of product, systems, AI and go-to-market strategy.

Key Responsibility Areas
Own the internal AI operating model for GTM — the library of skills, agent evals, cost, adoption and ROI — in partnership with Data and Enablement.
Keep the team a step ahead as customer zero for AI, turning what works into patterns other functions adopt.
Own the long-term design of the GTM stack — CRM, marketing automation, CS tooling — deciding what to build vs. buy.
Help the company prioritize by identifying the best solution to each business problem and sizing its cost and feasibility.
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.
Run vendor management end to end: evaluations, the quarterly keep-or-kill review, and renewals.
Partner as a peer to the leaders of Data, Enablement, Security, Finance and every commercial function.
Drive adoption and change management for new GTM capabilities across distributed teams.

What You'll Do

Within 1 month, you will:

• Know the team, the stack, and the cross-functional leaders and teams you’ll partner with
• Understand the main business challenges and opportunities for each GTM function
• Own the team's current quarterly objectives and the routines that keep them visible.

Within 3 months, you will:

• Have taken one major cross-functional change from plan to done
• Own the full vendor-renewal cycle across the commercial stack
• 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.

Within 6 months, you will:

• 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.
• 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.
• Have a 12-18 month roadmap, setting the high-level vision across our systems infrastructure, ways of working, and AI portfolio

Within 12 months, you will:

• Show, in numbers, the capacity the commercial organization reinvested because of what the team built.
• Have a development path agreed with each member of the team.
• Have the team recognized as the company's reference for AI-native operations

The Skill Set

• 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.
• 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.
• 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.
• 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.
• You define KPIs, run experiments, and use data to prioritize where to invest and to measure real impact on pipeline, conversion, efficiency and revenue.
• You drive strategic alignment and executive communication — conclusion first, tradeoffs named, complex topics made simple — and you drive change through to adoption.
• Thrive in ambiguous, fast-moving environments where the first version of the strategy has to be shaped, tested and improved quickly.
• Run vendor evaluations end to end
• Set and hold standards for documentation, testing and deployment without slowing the team down, and coach senior ICs …