Toast is driven by building the all-in-one restaurant platform that helps restaurants operate their business, increase sales, engage guests, and keep employees happy. We are searching for a forward-thinking, hands-on leader to join our GTM Strategy & Operations team as Director, GTM AI Solutions. Our GTM Strategy & Operations team drives accelerated growth by analyzing market dynamics, shaping strategic initiatives, and optimizing sales and onboarding methodologies and processes. This strategic execution directly impacts Toast’s trajectory in a rapidly evolving industry.
In this role, you will identify, evaluate, pilot, and launch the next generation of AI technology tools to drive efficiency and impact across our sales and customer onboarding organizations. This is a unique opportunity to shape how our teams use AI to deliver outstanding results and an excellent customer experience. You’ll collaborate across sales, onboarding, and systems teams, roll up your sleeves to build or demo new tools, and be a champion for innovation in our go-to-market strategy. If you’re energized by the chance to shape how world-class sales and onboarding teams unlock value with AI, we want to talk to you!
Do you have the right ingredients*? (Requirements)
- Deep passion for and knowledge of cutting-edge AI technologies and their applications in business
- 7+ years in GTM strategy, sales operations, or sales enablement, with hands-on exposure to technology adoption
- Strong understanding of sales and customer onboarding processes and KPIs
- Working knowledge of Salesforce CRM—including customizations, integrations, and reporting
- Demonstrated ability to lead cross-functional projects and collaborate with technical and commercial teams
- Experience running tool evaluations, pilots, and building business cases for new technology
- Willingness to “get in the weeds” and prototype or configure tools directly (e.g., building AI agents, testing integrations)
- Excellent communication, project management, and change management skills
Special Sauce* (Nice to Haves)
- Experience implementing AI tools or solutions in a sales or customer success environment
- Familiarity with sales tech stack including sales engagement, forecasting, and enablement platforms
- Background in consulting or product management
- Published thought leadership in the AI or GTM technology space
Our Spread* of Total Rewards
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.
*Bread puns encouraged but not required
#LI-REMOTE
The base salary range for this role is listed below. The starting salary will be determined based on skills and experience. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions, if eligible), benefits, and equity (if eligible).