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 Senior Director, Revenue Productivity and GTM AI Solutions. Our GTM Strategy & Operations team drives accelerated growth by analyzing market dynamics, shaping strategic initiatives, and optimizing Sales & Onboarding methodologies and processes. This strategic execution directly impacts Toast's trajectory in a rapidly evolving industry.
In this role, you will build the vision to drive productivity and efficiency across our sales organization, and execute on identifying, evaluating, piloting, and launching the next generation of technology tools. You will manage a high-performing team responsible for driving sales technology adoption, performance optimization, and innovation. This is a unique opportunity to shape how our teams deliver outstanding results and an excellent customer experience, with a focus on AI solutions. 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 team unlock value with cutting-edge technology, we want to talk to you!
About this roll* (Responsibilities)
- Build a systems and process-based sales strategy and roadmap to achieve company goals
- Lead, mentor, and develop a team of strategy and operations professionals focused on sales productivity and technology adoption
- Continuously scout, identify, and evaluate new AI tools for sales and customer onboarding use cases
- Lead pilots and proof-of-concept efforts, including hands-on configuration and building of AI agents where needed
- Run comprehensive demos and facilitate tool comparisons for cross-functional stakeholders
- Develop business cases for new tools, clearly articulating ROI, effectiveness, and scalability
- Drive cross-team alignment and collaboration between GTM, Sales, Onboarding, Operations, Systems, Marketing, and R&D teams for successful AI adoption
- Design and implement operational rollout plans, including training and change management
- Create feedback loops to iterate on tool effectiveness and expand adoption where successful
- Serve as the subject matter expert on opportunities and trends for the GTM organization
- Stay actively engaged with the external sales technology and AI ecosystem, keeping the company at the cutting edge
Do you have the right ingredients*? (Requirements)
- Deep passion for and knowledge of sales technologies and AI applications in business
- 10+ 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
- Proven experience managing and developing teams, with a track record of driving results through people leadership
- 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
- Strong executive presence and ability to drive cross-functional alignment across senior stakeholders
Special Sauce* (Nice to Haves)
- Experience implementing AI tools or solutions in a GTM 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
AI at Toast
At Toast 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 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).
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.
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