Head of GTM Systems & AI (m/f/d)

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.

• 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.

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

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 with care.

Fluent English (US/UK) / B2 level or equivalent (FR).

Enthusiasm for our working environment explained here: https://bit.ly/Convexity360L

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360Learning enables companies to upskill from within by turning their experts into champions for employee, customer, and partner growth. With our LMS for collaborative learning, Learning & Development teams can accelerate upskilling with the help of internal experts instead of slow top-down training. 360Learning is the easiest way to onboard and upskill employees, train customer-facing teams, and enable customers and partners–all from one place.

360Learning powers the future of work at 1,700 organizations. Founded in 2013, 360Learning has raised $240 million with 400+ team members across North America and EMEA.

In concert with our culture, 360Learning believes learning includes everyone and that means embracing the strengths of diversity, connectedness, and inclusion. Through conscientious efforts, our global footprint celebrates cultures, perspectives, and experiences from all over the world to support our platform that is built for all regardless of race, ethnicity, gender identity or expression, sexual orientation, religion, age, neurodiversity, disability status, citizenship, veteran status or any other aspect which makes an individual unique or protected by laws and regulations in the locations where we operate. Thus, 360Learning is proud to be an equal opportunity workplace, and we commit to continue this throughout our processes for recruitment, compensation, benefits, performance, promotion, and all other conditions and terms of employment. We want to learn from and with you!