GTM Enablement Engineer

Toast creates technology to help restaurants and local businesses succeed in a digital world, powering business owners to operate, increase sales, engage customers, and keep employees happy. The Revenue Productivity team is looking for a GTM Enablement Engineer to ensure our GTM tool investments actually land in the field. You'll own rep onboarding and ramp infrastructure, tool adoption measurement, playbook development, and the coaching systems that help managers develop their teams faster. This role sits at the intersection of sales process, AI tooling, and rep productivity — and is accountable to adoption rates, ramp velocity, and measurable hours returned to selling. A day in the life (Responsibilities) Prototype new automation and intelligence workflows based on direct field feedback — move fast from "reps are losing deals here" to a working proof-of-concept that can be tested, measured, and scaled Execute rigorous A/B testing across various vendors and agentic configurations to determine which capabilities truly accelerate revenue; apply a data-backed methodology to every stack decision to ensure measurable field impact Own the GTM enablement technology roadmap: set strategy for which tools, integrations, and AI capabilities to build or buy next, prioritized by rep productivity impact and grounded in data from adoption metrics, call analysis, and win/loss patterns Develop AI-assisted templates and playbooks for outreach, meeting prep, and post-call follow-up that reps and managers actually use Embed with the sales team — ride deals, listen to calls, and map every stage of the buyer journey to understand where reps win, stall, or lose and why Partner with Sales Enablement and frontline managers to surface AI-generated coaching recommendations from call data, so managers are reviewing flagged moments rather than full recordings Build rep scorecards and deal health dashboards using conversation intelligence and engagement data to give managers real-time visibility into rep performance and deal risk Measure automation adoption and time savings; report on hours returned to the field per quarter and iterate based on what's working Engineer tight feedback loops from post-call notes, win/loss data, and customer conversations into structured inputs that improve playbooks, messaging, and product roadmap Architect and maintain GTM stack integrations with clean, validated data flows and minimal manual touch Serve as internal SME and trainer ensuring reps and managers extract full value from automated workflows — and feed learnings back into the roadmap What you'll need to thrive (Requirements) 4+ years in Sales Enablement, Revenue Operations, or GTM Engineering, with at least 2 years owning rep-facing tooling, coaching infrastructure, or workflow automation in a sales environment Hands-on experience with conversation and revenue intelligence platforms (Gong, Revenue.io, Chorus, or similar) — you've built scorecards, coaching workflows, or deal health views, not just administered the tool Demonstrated ability to embed deeply with sales teams and translate what you hear in the field into systems, playbooks, and automation that change rep behavior Agent building: Demonstrated experience designing, building, and deploying AI agents and agentic workflows that transformed real work — not just using AI, but building with it Experience building and owning adoption measurement frameworks — you track what gets used, report on impact, and use that data to iterate Strong communicator and facilitator who can train non-technical audiences, run enablement sessions, and build buy-in for new tools and workflows across sales leadership and frontline reps Systems thinker who can connect tools, trace data flows, and maintain integrations across the GTM stack — comfortable with APIs, Salesforce flows, and no-code/low-code automation tooling What will help you stand out (Nonessential Skills/Nice to Haves) Experience building win/loss programs end-to-end,