Chief of Staff / Strategic Operations Lead

Palo Alto, CA - Hybrid 

Bolo AI is building the next-generation agentic AI platform for heavy industry, making it faster, safer, and better. Our intelligent context layer unlocks heavy industry's operational data and institutional knowledge, making it usable, actionable, and accurate enough for the decisions the world depends on.  

Our early customers are seeing real results — from catching critical equipment failures hiding in plain sight to automating production optimization workflows that were previously done in spreadsheets. We are backed by leading venture investors. As we grow, we are building a company that can move fast, serve demanding enterprise customers, and maintain a high bar for quality. We are AI-native: we use AI agents internally across every function, and we expect everyone on the team to work that way. 

Role Overview: 

We're at an inflection point. The product is proven, customers are seeing real results, and the pipeline is moving faster than we expected. This role sits in the CEO's office, with ownership across execution, AI tooling, and customer-facing work. You will drive follow-through on the company's highest-priority commitments, build the lightweight AI workflows that make the team more productive, and help keep customer engagements on track. It is high-trust, hands-on, and spans the full breadth of the business. 

CEO Leverage & Strategic Execution 

• Turning CEO priorities into clear workstreams, owners, timelines, and follow-through. 

• Creating meeting briefs, follow-up plans, decision memos, and operating artifacts. 

• Identifying blockers early and helping resolve them without unnecessary escalation. 

AI Tooling and Workflows 

• Identify the highest-leverage automation opportunities across GTM, customer delivery, and internal ops. 

• Build, test, and iterate on AI-assisted workflows scrappily and quickly. 

• Maintain and improve what you build as the company's needs evolve. 

GTM & Strategic Support 

• Maintain visibility into account priorities, deal status, and pipeline health. 

• Help run structured hiring processes for high-priority roles — scorecards, interview loops, candidate follow-up. 

Must-Haves 

• 5+ years of professional experience, with meaningful time in a startup or high-velocity tech environment. 

• Highly proactive and execution-oriented: you move fast with attention to detail. 

• Strong written communication: from raw notes to exec-quality output quickly. 

• Comfortable in ambiguity and complexity: you can take a vague prompt, figure out what matters, and produce something useful. 

• Scrappy and resourceful: you have built or shipped things end-to-end, even if imperfectly. Hands-on with AI tools 

• Based in the Bay Area and willing to work hybrid from Palo Alto, with travel as needed. 

Nice-to-Have 

• MBA or equivalent business training. 

• Consulting, investing, or enterprise GTM background. 

• Exposure to Energy, industrials, infrastructure, or complex B2B software. 

You will work directly with the CEO on the company's most important work while having outsized impact on how we operate and scale. You will see how enterprise customers are won, how product direction is shaped by real-world deployments, and how a company builds operating infrastructure at the moment it matters most. For the right person, this role has no ceiling. It is designed to evolve into operations, product, customer delivery, or something we haven't created yet, based on where the company needs most and what you are best at. 

What We Offer:  

• Competitive Compensation: A strong base salary plus performance-based commission.  

• Ownership & Impact: Equity options so you can share in our success as we grow and shape the future together.  

• Hybrid Work Environment: Enjoy a flexible hybrid schedule—collaborate in person and work from home.  

• Growth & Opportunity: Join us at a pivotal stage where your contributions will have a direct impact on our journey. As we grow, so will your opportunities.  

• Culture of Respect & Collaboration: We live by humility, respect, and low ego. You’ll be part of a team that values your ideas and celebrates wins together.