Chief of Staff to the CEO
About the role
The organization is building the future of work: the first truly converged AI workspace unifying tasks, docs, chat, calendar, and enterprise search, all supercharged by context-driven AI. This is an AI-native organization. Every team member is expected to leverage AI daily, and AI fluency is evaluated as part of the hiring process. Join to help redefine what's possible. 🚀
Chief of Staff to the CEO
This role is not about "professionalizing" operations. It's about finding a force multiplier for a highly engaged, product-obsessed CEO who operates at a high frequency. This role is distinct because the individual will be a testament to how AI transforms individual capabilities. The expectation is to be weaponized by AI, operating at a level that would have previously required a team of ten.
Why This Role Exists
The individual will serve as the connective tissue between the CEO and the rest of the organization. This role combines operator, strategist, translator, and architect of a new way of working. The goal is to make the CEO faster, the leadership team more aligned, and the organization more coherent in execution, by refusing to adhere to old methods.
Operating System Design
Establish the operating rhythms for a hypergrowth organization: weekly leadership syncs, monthly business reviews, quarterly planning, and annual strategy. Define formats, own preparation, and drive follow-through. Build these processes with an AI-first approach from day one, incorporating automated briefings, agent-driven preparation, and real-time synthesis.
AI Transformation Leadership
Partner with the CEO to challenge every function to question existing processes. Focus on total reinvention from first principles, not just optimization or automation of current workflows. Challenge leaders to decompose workflows, identify tasks for agents, eliminate unnecessary steps, and determine where human judgment is irreplaceable. Drive the organization to stay ahead in the industry-wide shift in how companies operate.
CEO Intelligence Layer
Build AI-powered systems to make it sustainable for the CEO to remain deeply involved in details at scale. Determine what the CEO sees, when, and in what format, architecting a filtering system for signal over noise. Develop the intelligence infrastructure to ensure the CEO is the most informed person in every conversation, meeting, and review.
Industry & Competitive Immersion
Build information loops, powered by agents and human curation, to keep the CEO embedded in the competitive landscape, market shifts, emerging technology, customer feedback, and analyst insights. Ensure the CEO is consistently ahead of industry trends.
Strategic Program Execution
Intake CEO-generated priorities, scope them, assign ownership, track progress, and ensure successful delivery. Serve as the accountability layer for ensuring initiatives are shipped.
Board & Investor Operations
Own the preparation cycle for board meetings, including narrative development, data assembly, materials review, and dry runs. Develop a compelling narrative that positions the organization as a defining company of the AI era.
Cross-Functional Reinvention
Act as an escalation point for inter-team work. Challenge existing processes within any function, driving them to kill and rebuild from zero based on first principles. Push teams to rethink their operations, leading to increased output.
Leadership Team Cohesion
Monitor the operating dynamic of the executive team, surfacing misalignment early and facilitating resolution. Ensure the leadership team channels pressure into momentum, not friction.
Internal Communications & Narrative
Reinforce the organization's thesis on how companies will work for the next twenty years. Shape how the CEO communicates with the organization, drafting talking points and memos. Ensure every employee understands their role in reshaping the industry.
What You're Measured On
After one year: A functioning CEO office operating on AI-native systems and cadences that are impossible to replicate manually. The CEO's calendar reflects a deliberate shift toward product, external, and strategic time, while maintaining deep detail orientation. At least 3 functions have undergone first-principles workflow redesign with measurable results, including fewer people doing more, agents handling grunt work, and leaders freed for strategic thinking. The leadership team is more aligned, less bottlenecked, and rewired to question "why" before "how." Board preparation is seamless, with a narrative positioning the organization as the defining AI-era company. At least 3 major cross-functional initiatives have shipped that would have otherwise stalled. The organization is cited externally as a case study for AI-era operations, with this role being a significant contributor.
Who Thrives Here
Prior experience operating at the right hand of a founder-CEO in a company with 500+ employees, understanding the difference between supporting a CEO and creating leverage. Proven ability to build operating cadences and structures, not just inherit them. 6+ years in strategic operations, management consulting, or a prior Chief of Staff role. 3+ years of people management experience, with a track record of building elite teams. Fluency in pre-IPO dynamics, including governance, compliance readiness, investor relations, and board management. Demonstrated AI power user status: personal workflows rebuilt around AI, daily use of agents, prompting, and automation to achieve exceptional output. This must be demonstrable live. First-principles thinking: instinct to question the existence of processes rather than just optimize them, with proven experience leading teams through reinvention. Ability to move fast without sacrificing quality, with good judgment on when 80% is sufficient and when perfection is required. High emotional intelligence and low ego, with a focus on making others look brilliant. Comfort with ambiguity and a proactive approach to challenges.
Who Should Not Apply
Individuals seeking stable, well-defined scope; the scope is dynamic and tied to the CEO's needs. Those viewing the Chief of Staff role as a stepping stone to COO; this is a distinct discipline. Individuals who only "use ChatGPT sometimes"; a fundamental alteration of professional output through AI is required. Those who feel threatened by the question "why do we do this?" Individuals who prioritize consensus over velocity. Those without experience in high-growth tech or SaaS environments.
Compensation & Details
Reports to: CEO
Location: Remote (US), with regular travel to San Diego HQ
Compensation: Competitive base salary + significant equity. Compensation philosophy rewards outsized leverage, which this role embodies.
Why You'd Want This
This may be one of the most leveraged non-founder roles in SaaS. Be at the center of the organization defining how AI reshapes organizations, not theoretically, but in production with AI agents and a CEO committed to innovation. Actively drive transformation across functions, processes, and assumptions. Gain insight into every decision before it's made, have the CEO's ear, and earn the executive team's trust. Challenge smart people to think critically about their work and push the organization to move at an unprecedented speed. Define the future of this role as other companies adopt similar positions.