Chief of Staff

Presto is the leading Voice AI company for restaurant drive-thrus, operating at scale in complex, noisy, customer-facing environments. As the AI partner to more than a dozen of the most iconic American restaurant brands, Presto is building one of the most impactful real-world applications of AI that directly impacts revenue, labor efficiency, and a magical guest experience for millions of people.

AI is not a feature at Presto—it is the foundation of how we build, evaluate, and evolve our products. We operate at lightning-speed iteration cycles and are solving some of the hardest problems in Voice AI. We are backed by Remus Capital, were a Y Combinator company, and are headquartered in Silicon Valley.

This may not be the right fit for you if you are looking for a traditional 9-to-5 environment. We move at the pace of AI. Change is constant, and roadmaps evolve quickly. Presto is for builders, experimenters, and problem-solvers who thrive in ambiguity, learn continuously, and are excited to shape the future of real-world AI alongside a high-performance team.

The Role

We are looking for a Chief of Staff to the CEO located in the Bay Area, or Chicago, IL to partner closely with Presto’s leadership team and support the execution of our most strategic initiatives across engineering, product, and company operations.

This is a highly impactful role at the intersection of technology, strategy, and execution . You will work directly with the CEO and senior leadership to drive critical projects, translate technical insights into strategic decisions, and ensure alignment across teams as Presto scales its Voice AI platform.

Success in this role requires a strong technical foundation , an ability to operate across engineering and business contexts, and exceptional problem-solving and communication skills. The ideal candidate combines engineering or AI expertise with a strategic mindset and thrives in fast-moving environments where priorities evolve quickly.

What You’ll Do

• Partner directly with the CEO to drive strategic initiatives across the organization, including: engineering, product, and company operations.
• Act as a connective layer between leadership, engineering, product, and go-to-market teams to ensure alignment on priorities and execution.
• Translate complex technical concepts into clear strategic insights to support leadership decision-making.
• Lead cross-functional projects from concept through execution, ensuring milestones and outcomes are achieved.
• Support product and engineering teams by identifying operational bottlenecks and improving collaboration across teams.
• Analyze data, metrics, and technical outputs to help inform company strategy and roadmap priorities.
• Co-chair the AI and Automation Steering Committee to drive technical improvement and automation across the organization.
• Prepare strategic materials, internal briefings, and presentations for executive discussions and board meetings.
• Drive operational efficiency and help scale processes as the company grows.
• Serve as a thought partner to the CEO on organizational strategy, technology direction, and company growth initiatives.
• Act as a proxy for the CEO, ensuring proper prioritization and working with key leaders to drive organizational priorities

What We’re Looking For

• Bachelor’s degree in Business, Computer Science, Engineering, or a related technical field (or equivalent practical experience).
• 3-5 years of experience in engineering, product, strategy, or technical operations roles.
• Strong technical background with familiarity in AI, machine learning, or advanced software systems.
• Ability to understand complex technical architectures and communicate them clearly to cross-functional stakeholders.
• Proven ability to drive complex projects across multiple teams and functions.
• Exceptional problem-solving, analytical, and communication skills.
• Strong executive presence and ability to work closely with senior leadership.
• Comfortable operating in fast-moving, ambiguous environments where priorities evolve quickly.

Nice to Have

• Background in startups or high-growth technology companies.
• Prior experience supporting senior executives or working in strategy / chief of staff roles.
• Experience working with product and engineering teams to drive technical initiatives.

Why Presto

We move at the speed of AI. Change is rapid, experimentation is expected, and roles evolve alongside the technology. This is not a highly prescriptive environment—success requires curiosity, adaptability, and a desire to continuously learn and push boundaries.

You’ll work on real-world AI systems at meaningful scale, with direct impact on the company’s strategy and execution. This role offers significant visibility and ownership across the organization while partnering closely with senior leadership to shape the future of Presto’s Voice AI platform.

Location

This role is based in the San Francisco Bay Area and will operate on a hybrid schedule from our San Mateo, CA office .

Compensation for this role is equity-focused , with an on-target earnings (OTE) range of approximately $130,000–$200,000 annually , depending on experience and level.

Presto’s compensation philosophy rewards high performers and aligns incentives with long-term value creation through meaningful equity participation.

Benefits for U.S.-based employees include medical, dental, and vision insurance, a 401(k) program, and paid time off (PTO). Learn more at .

Our Commitment

We value people from all walks of life and are committed to building an inclusive, equitable work environment. We strongly encourage candidates from historically underrepresented backgrounds to apply. Presto Phoenix, Inc. is an equal opportunity employer.

If you need an accommodation to access the application or interview process, please contact View email address on click.appcast.io .