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, including data capture design, analysis, and structured synthesis back to Sales, Product, and Marketing
- Familiarity with sales engagement platforms (Outreach, Salesloft) and how to connect coaching insights into sequence strategy and messaging iteration
- Background working closely with Sales Managers on performance management frameworks — rep scorecards, pipeline inspection rituals, or QBR prep tooling
- Experience in a high-growth SaaS or fintech environment where you've scaled enablement infrastructure across a rapidly growing sales team
AI at Toast
At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.
Our Total Rewards Philosophy
We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.
The starting pay rate for this role is below. Please note that there is no range for this role; the rate listed below is the only rate. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.
How Toast Uses AI in its Hiring Process
Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. To learn more: https://careers.toasttab.com/ai-in-hiring
Diversity, Equity, and Inclusion is Baked into our Recipe for Success
At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.
We Thrive Together
We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast.
Apply today!
Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact [email protected].
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For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.
Toast Boston, Massachusetts, USA Office
Toast’s headquarters is located in the heart of the Seaport District. Toasters are surrounded by art, culture, and delicious cuisine in one of the most bustling neighborhoods in Boston.
Early Careers
Toast's Early Careers program is designed to launch students' careers by integrating them into the company's vibrant culture and impactful work. Interns and co-ops are treated as full-time Toasters from day one, given meaningful projects, and provided with mentorship from industry professionals. The program emphasizes hands-on learning, collaboration across teams, and the autonomy for students to develop and showcase their skills, supported by consistent feedback. Toast offers opportunities across various departments, including technical roles like Software Engineering and Data Science, as well as non-technical roles such as Human Resources and People Operations.
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