Chief of Staff

Presto•San Mateo, CA

6d•$130,000 - $200,000•Hybrid

About The Position

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. We are looking for a Chief of Staff to the CEO 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 and an AI-native mindset, 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. You should already be using AI tools daily to amplify your own output, and you should be excited to bring that same leverage to every function at Presto.

Requirements

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 hands-on experience using AI tools (LLMs, AI coding assistants, automation platforms) to drive real output, not just theoretical familiarity.
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.
Demonstrated AI-native working style: you default to using AI for research, analysis, drafting, coding, and decision support, while applying rigorous validation and critical judgment to AI-generated outputs. You can point to concrete examples of how AI tools have multiplied your personal or team output without sacrificing accuracy.
Comfort with technical concepts like APIs, data pipelines, prompt engineering, and AI model evaluation, with the ability to bridge conversations between engineering teams and business stakeholders.

Nice To Haves

Background in startups, consulting, 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.
Experience building internal tools or automations using AI-assisted development (e.g., Claude, Cursor, Copilot, Replit, or similar).
Familiarity with the Voice AI, NLP, or conversational AI landscape.
Track record of driving AI adoption or digital transformation initiatives within an organization.

Responsibilities

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.
Champion AI adoption across the organization by identifying high-leverage opportunities to integrate LLMs, automation, and AI-powered tooling into day-to-day workflows.
Build and maintain internal tools, dashboards, and automations using AI-assisted development (e.g., AI coding assistants, no-code/low-code platforms, API integrations) to solve operational problems at speed.
Evaluate and recommend emerging AI products, frameworks, and workflows that can accelerate Presto's operations, go-to-market, and product development.
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.