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Senior Manager, Software Engineering - Toast IQ

Toast · Remote · R & D : Engineering : Commerce

Posted Sep 29, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you built or rebuilt an engineering team. How did you decide who to hire?

What they are checking: Whether they hire deliberately for the gaps on the team rather than for generic seniority.

How do you work with Design and Product to make AI experiences feel crafted rather than bolted on?

What they are checking: Whether they collaborate as a true partner on experience quality, not just as the team that builds what's specified.

Tell me about a time you had to deliver hard feedback to a senior engineer.

What they are checking: Whether they address performance issues directly and fairly instead of avoiding them.

How do you keep a team healthy when working at the frontier means a lot of ambiguity and changing direction?

What they are checking: Whether they protect morale and focus during constant change rather than passing the churn straight to the team.

What would you do

The posting talks about tending the platform for internal teams: documentation, feature lifecycle and evaluation. What would you fix first?

What they are checking: Whether they understand platform work as a product for other engineers and can prioritize what unblocks them.

An agent automates a back-office task for restaurants and occasionally gets it wrong. How do you decide what level of error is acceptable?

What they are checking: Whether they weigh the cost of mistakes to the operator and design safeguards like review steps.

Your team is pulled between new AI features and stabilizing what's already shipped. How do you decide?

What they are checking: Whether they balance growth and reliability with clear reasoning they can explain to leadership.

About the work

How would you shape the technical vision for Toast IQ when the underlying LLM capabilities change every few months?

What they are checking: Whether they can set direction that holds up as models shift, rather than betting everything on today's capabilities.

How do you evaluate whether an agentic workflow is good enough to put in front of every Toast customer?

What they are checking: Whether they treat evaluation as an engineering discipline with real test sets and thresholds, not demos.

How do you manage the cost and latency of LLM calls at the scale of every Toast customer?

What they are checking: Whether they think about the economics and performance of AI features, not just accuracy.

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The full job description

As published by Toast.

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. At Toast, we’re transforming how restaurants operate and grow. Our platform combines intuitive technology with a deep focus on customer success. From streamlining operations to delivering standout guest experiences, we empower restaurants to thrive through smart design and data-driven innovation. As a Senior Engineering Manager for Toast IQ, you will fundamentally redefine the value and partnership Toast can offer to businesses. You and your team will build at the frontier of LLMs and agentic workflows, with a heavy focus on automating and improving the unglamorous work so that our customers’ daily focus can be more of what they actually love about the hospitality industry. You will work closely with Design and Product to chart a course for thoughtfully designed and carefully crafted AI experiences that unify and expand the Toast ecosystem.  A day in the life (Responsibilities) • Shape and steer the technical vision and execution for Toast IQ, a high-growth and high-potential AI offering for every Toast customer. • Thoughtfully garden-tend the platform for internal teams to build and expand on top of. Better documentation, better feature lifecycle management, and better evaluation. • Break down large platform and product initiatives into clear, incremental milestones, then deliver measurable outcomes with consistency and quality. • Establish and uphold AI toolchain standards, architecture patterns, and best practices across the organization. • Coach and mentor engineers and managers, helping them grow technically and as leaders. • Operate effectively in a fast moving environment where experimentation, iteration, and platform stability must coexist. • Champion the use of AI tools and practices to accelerate development, improve team velocity, and pioneer new ways of building - setting the bar for what it means to be an AI-first engineering organization. What you'll need to thrive (Requirements) • 5+ years of experience leading high performing engineering teams in production environments. • Strength in modern backend architecture: thoughtfully designed API surfaces, microservices that scale safely, and performance that improves consistently. • Fluency in modern mobile and web architecture, including component libraries, build systems, CI/CD, and microfrontend patterns. • Experience owning or contributing to internal developer platforms that support multiple product teams. • Interest and investment in where LLMs and agents can be the right tool for a customer need and rigor/principles around where they may not be. • Demonstrated success partnering with product and design stakeholders to deliver highly crafted experiences that map novel interaction patterns directly to a customer need. • Ability to translate broad strategic goals into clear technical roadmaps and execution plans. • Strong communication and leadership skills with experience influencing senior technical, product, and design leaders. • Track record of mentoring engineers and building inclusive, high ownership teams. Bonus Ingredients (Nice to Have) • Strength and familiarity with the toolchain that drives modern LLM and agent experiences: system prompts, harnesses, skills, tools, and evals. 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 . #LI-REMOTE 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 . ------ 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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