Chief of Staff

Lanai • Palo Alto, CA

11d • Onsite

About The Position

Lanai is building the missing infrastructure layer for the AI era. Our Enterprise AI Observability and Governance Platform gives enterprises real-time visibility into how AI is actually being used across the organization—at the prompt level, across every tool—solving the critical challenge blocking AI ROI: you can't scale what you can't see. Think: Databricks for AI workflows. Founded by technical leaders who built core infrastructure at Google, VMware, Meta and Splunk, we've raised capital from Lux Capital (Hugging Face, Databricks), Juxtapose, F7 Ventures, and BAG Ventures. Fortune 1000 companies are deploying our platform to discover the AI usage leadership doesn't know exists, scale what's working, and govern the transformation safely. Living our values enables us to foster trust, take risks, and achieve extraordinary results together: Curiosity: Question openly, learn quickly, share knowledge Community: Celebrate diversity, unite in purpose, practice empathy Commitment: Maintain high standards, honor promises, focus on impact Clarity: Communicate directly with care, bring focus to ambiguity Located in Palo Alto, our highly-technical, nerdy (and nice!) small team brings together enterprise leaders from SignalFx, VMware, Google, and Meta. We're advised by industry leaders including Fredrick "Flee" Lee (CISO at Reddit), Raghu Raghuram (former VMware CEO), and Yvonne Wassenaar (former CIO of New Relic). The Opportunity This is a rare seat at the table during the most critical phase of a startup's journey: the path from Seed to Series A and beyond. You'll be the strategic partner to Lexi Reese, the co-founder and CEO, building the revenue engine and operational foundation that will fuel our next round of growth. If you've been in consulting or banking and are ready to see strategy through to execution, or if you've been in startup ops and want to level up to true strategic partnership, this is your opportunity to own outcomes that directly impact company trajectory.

Requirements

• Top-tier MBA or equivalent experience (MBB consulting, bulge bracket banking, or Big 4 strategy)
• 3-5 years post-MBA in high-intensity environments where you learned to work fast and work smart
• 2+ years in startup operations where you got your hands dirty building systems from scratch
• Track record of completion - you've shipped real projects with measurable outcomes
• Enterprise software exposure - you understand B2B sales cycles, procurement, and enterprise buying
• Strategic synthesis and insights: You connect dots others miss and turn insights into action
• Systems thinking: You build processes that scale without breaking
• Analytical rigor: You model scenarios, pressure-test assumptions, and quantify uncertainty
• Operational excellence: You sweat the details and finish what you start
• Stakeholder management: You influence across functions and manage up effectively
• Comfortable with ambiguity: You thrive when the path isn't clear
• Anticipates the CEO's next question before it's asked
• Documents decisions so thoroughly that context never gets lost
• Flags problems early with proposed solutions, not just issues
• Finishes projects completely rather than leaving them at 80%
• Prioritizes ruthlessly based on company goals, not what's easy
• Communicates proactively about status, blockers, and tradeoffs
• Generates insights from data rather than just reporting numbers

Responsibilities

• Own pipeline dynamics: accurate forecasting, deal progression analysis, win/loss patterns
• Implement and optimize Hubspot as our revenue command center
• Develop pricing models and contract structures for enterprise deals
• Create buyer persona frameworks and competitive positioning
• Build dashboards that enable data-driven decision making
• Transform CRM from admin tool to strategic asset
• Own board materials, investor updates, and fundraising documentation
• Build and maintain financial models that guide capital allocation decisions
• Create systematic decision frameworks for resource prioritization
• Implement knowledge management systems that scale with headcount
• Drive cross-functional initiatives from strategy through execution
• Design processes that create leverage, not overhead
• Synthesize customer conversations into strategic insights
• Build competitive intelligence framework tracking 20+ vendors
• Document buying patterns: who buys, why they buy, how they decide
• Create "Voice of Customer" packages proving product-market fit
• Partner with product/engineering to translate market signals into roadmap
• Identify emerging trends before they're obvious

Benefits

• High Ownership: Design and build critical systems from the ground up versus joining established companies where core architecture decisions are already made
• Unmatched Financial Upside: Early equity in a SaaS AI governance and data analytics company with early exercise
• Exceptional Leadership Access: Work directly with co-founder/CEO Lexi Reese (Google, Gusto, Meta), co-founder/chairman Steve Herrod (original CTO of VMware, investor @ General Catalyst + Juxtapose), CTO Rajesh Raman (supported tech infra that took Meta/Google public before moving to SignalFX, Splunk) and CPO Mohit Mehta (Splunk, Nvidia)
• Health, dental, and vision insurance
• Unlimited PTO

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level