About this role.
Toast is seeking a senior AI operations leader to connect its Toast IQ agentic-AI strategy with cross-functional execution, market launches, and customer adoption. The role owns portfolio visibility, operating rhythms, dependencies, launch readiness, strategic insights, and the translation of technical capabilities into commercial value. It partners closely with product, engineering, design, marketing, sales, and support while working directly with the VP of Product. Success requires strong product and go-to-market judgment, executive-ready communication, analytical rigor, and comfort personally driving ambiguous work to completion. This is a high-impact leadership role focused on scaling an AI product portfolio for restaurant and local-business customers.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would establish a shared portfolio cadence with a concise view of each initiative's customer problem, owner, stage, dependencies, risks, launch date, success metrics, and key decisions. I would pair this artifact with recurring decision-focused reviews so leaders can resolve tradeoffs quickly rather than merely receive status updates.
I would define a measurement framework before launch covering readiness, activation, adoption, engagement, customer outcomes, operational quality, and commercial impact. I would segment results by customer type and use qualitative feedback alongside telemetry to identify whether gaps are in positioning, enablement, product experience, or underlying model performance.
I start with the operator's workflow, pain point, and measurable desired outcome rather than the technical implementation. I then articulate the capability in plain language, validate it with customer evidence, and equip go-to-market teams with demonstrations, proof points, objections handling, and clear boundaries on what the product can reliably do.
In an ambiguous initiative, I first align stakeholders on the decision to be made, the intended outcome, and a small set of evidence needed to proceed. I create a practical workback plan, assign accountable owners, surface tradeoffs early, and maintain momentum through short decision-oriented checkpoints until the outcome is delivered and measured.
I would monitor customer workflow pain points, adoption and retention data, competitive launches, agent reliability patterns, model capability and cost changes, regulatory developments, and feedback from sales and support. I would synthesize those inputs into explicit strategic implications, such as where to invest, what to package differently, and which use cases require stronger evaluation or guardrails.
Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.
About the Role:
Toast IQ is our agentic platform for local business: a growing set of specialized AI agents and capabilities designed to take real work off an operator’s plate, from driving demand and managing labor to optimizing the back office. As we expand this portfolio across multiple lines of business, we need to ensure that what we build comes together as a coherent platform, reaches the market effectively, and produces meaningful customer and business impact.
The AI Operations Lead will help build and run the operating system that connects AI strategy to execution and market impact. You will help shape how our AI portfolio comes together, is launched, and adopted, building the operating engine that brings this experience to life, and turning customer, market, and technology signals into better product and commercial decisions.
This is a highly cross-functional, hands-on leadership role. You will work directly with the VP of Product for Toast IQ, partnering across product, design, engineering, marketing, sales, and support to bring the vision of Toast IQ to life. Success will require strong judgment, exceptional communication, and the ability to personally drive ambiguous work to completion.
A day in the life (Responsibilities)
- Create visibility across Toast’s broader AI efforts and run portfolio ops. Connect work happening across the agent portfolio and other AI initiatives. Share learnings, identify opportunities to reuse capabilities, and surface key decisions. Maintain visibility into ownership, sequencing, dependencies, key decisions, risks, progress, and enablement.
- Build Toast’s AI presence. Partner with product, design, engineering, and marketing to make Toast’s AI products, technical insights, customer outcomes, and talent more visible through launches, customer stories, product and engineering content, and social channels both internally and externally.
- Turn high-impact ideas into action. Identify opportunities to accelerate Toast’s AI strategy, develop a strong point of view on what we should do, and have the ownership to run at the best ideas, bringing the right people together and driving the work from concept to tangible outcome
- Help shape the AI portfolio strategy. Partner with product and business leaders to define target customers, priority use cases, positioning, packaging, sequencing, and launch plans across Toast’s AI portfolio.
- Build an AI-powered engine that gets smarter over time. Use AI to continuously synthesize customer insights, product performance, market shifts, and changes in the underlying technology, turning signals from across the business into actions that improve our products, priorities, and how we bring them to customers.
- Turn a fast-moving AI market into an advantage. Stay up on what’s happening in AI and help translate emerging patterns into implications for Toast’s strategy
What you’ll need to thrive (Requirements)
- Fluent with AI products, including how they work and what patterns are leading within B2B and consumer markets.
- 5+ years of experience in product operations, business operations, go-to-market strategy, or product marketing, with experience working alongside product and engineering teams.
- Demonstrated ownership of complex or emerging products from development through launch, internal enablement, customer adoption, and ongoing market learning.
- Exceptional written and verbal communication, including the ability to turn complex information into a clear narrative for customers, go-to-market teams, and senior leaders.
- Track record of building repeatable, cross-functional operating models.
- Strong product and commercial judgment, with the ability to translate technical capabilities into clear customer value and compelling market narratives.
- Ability to move fluidly between strategy and execution, from shaping a portfolio narrative or launch plan to improving a demo, creating enablement, resolving a readiness gap, or synthesizing customer feedback.
- Strong analytical skills and experience defining the measures that indicate whether a launch is working.
- High judgment and comfort operating in ambiguity. You recognize what matters, make defensible decisions, surface the right questions, and personally drive work to completion
What will help you stand out (Nonessential Skills/Nice to Haves)
- Experience bringing AI/ML, agentic, platform, or other rapidly evolving technical products to market.
- Experience building a launch, commercialization, or adoption motion.
- Experience in a startup or high-growth environment where the role required significant range and adaptability.
- Experience developing customer proof, product demonstrations, or technical thought leadership.
- Vertical SaaS, SMB, or restaurant and hospitality technology experience.
- Familiarity with AI product evaluation and the commercial considerations associated with AI products.
- BA/BS or equivalent practical experience
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 base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.
Zone A
$181,000—$290,000 USD
Zone B
$157,000—$251,000 USD
Zone C
$142,000—$227,000 USD
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. We ask that you complete interviews and assessments on your own, without real-time AI tools, recording, or transcription bots, unless we tell you otherwise in advance. To learn more: https://careers.toasttab.com/ai-in-hiring
Our Approach to Hybrid Working
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 hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast
People Are the Secret Ingredient in Our Recipe for Success
At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry brings together people with a wide range of backgrounds, experiences, and perspectives, and we value that same breadth at Toast. We strive to build a culture grounded in authenticity, respect, and humility, where every Toaster has a real opportunity to grow, contribute, and do their best work—raising the bar in delivering exceptional experiences for our customers and each other.
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 candidateaccommodations@toasttab.com.
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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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