Executive Chief of Staff

Role Summary: 

The companies that define the next decade will be the ones who learned to move faster, decide smarter, and execute with precision, with AI at the core. OfficeSpace Software is building that company now, and the Executive Chief of Staff is a vital leader helping us get there. 

You'll report to the CEO and work directly with her and the Executive Leadership Team on the initiatives that move growth, efficiency, and the future of work forward. You'll own the operating rhythm that keeps the business in motion, lead AI activation across every function, and handle all of it with the judgment that comes from being trusted with things that matter. 

The work moves fast and stays visible. We need someone who can take a complex problem, run it down to a decision on their own, and come back with a clear answer. If that's the environment where you do your best work, we'd like to meet you. 

What You’ll Do 

Independent Initiative Ownership 

• Own strategic initiatives from scoping and alignment through execution and measurable results. 
• Turn executive priorities into clear, AI-enabled execution plans across functions. You'll have the room to make calls and move without waiting for direction. 
• Spot execution risks early and work the mitigations using predictive insight and scenario modeling. Bring the ones that matter forward, and clear what you can before it lands with the CEO. 
• Design and track KPIs that tie initiatives directly to revenue, efficiency, and profitability. You own the accountability for results, not just the reporting that describes them. 

AI Activation Leadership Across the Company 

• Be a highly visible internal champion for AI adoption. Work with the ELT to find where AI can shorten cycle times, take low-value work off people's plates, and push up what each function can deliver. 
• Partner with functional leaders to embed AI into core workflows, translating opportunity into adoption. 
• Build the playbooks, prompts, and patterns that turn one-off AI experiments into something the whole company uses. Define what AI-native operating looks like here. 
• Treat AI activation as a business outcome. Track adoption, productivity lift, and cycle-time gains across functions, and hold the organization to the progress those numbers describe. 

Operating Cadence & Cross-Functional Execution 

• Own the company's operating cadence: QBRs, executive rhythms, leadership forums, and everything in between that keeps a fast-moving business aligned and accountable. 
• Get cross-functional teams shipping faster, with tighter feedback loops and visibility in real time. You are the force multiplier that unblocks decisions and moves work forward. 
• Build the AI-powered operating systems (dashboards, copilots, workflows) that raise the speed and quality of decisions across the ELT. 

What You’ll Bring 

• 5–7 years in strategy consulting, SaaS operations, private equity value creation, or similarly demanding environments, with a record of owning outcomes rather than supporting someone else who did. 
• A track record of taking complex, ambiguous workstreams from problem definition through to a clear decision, independently, without waiting for someone to build the structure around you first. 
• Strong judgment. You know what needs to go up the chain, what you can handle yourself, and what stays with you.  
• Change management skills. You understand that transformation is at least as much about people and sequencing as it is about strategy, and you've helped organizations work through hard decisions, not just write them up. 
• Operator's mindset. You advise and you execute, owning outcomes the whole way.  
• Real AI fluency. You've used GenAI, automation tools, and data systems to make workflows faster and decisions sharper. You build with AI; you don't just open it up to ask questions. 
• Sharp analytical thinking. You turn data into clear decisions and you can run a financial model, a SaaS metric, and an executive narrative in parallel without losing the thread on any of them. 
• Executive presence. You're clear when you talk, you can move senior stakeholders, and you build trust fast even when there are people in the room with twenty more years of experience. 
• Strong financial and SaaS metric literacy. You can talk about how a decision moves ARR, NRR, EBITDA, and enterprise value, and you know what those numbers mean for this business specifically. 
• A 'Love to Win' attitude. You're pulled toward what success looks like more than you're pushed by fear of failing. Pace, optimism, and resilience are how you show up to hard problems. 
• Comfort in ambiguity. You bring structure, speed, and focus to complex problems, and you don’t wait to be told what comes next.