Role Summary: 

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

In this role, you will sit at the intersection of strategy, transformation, and execution—partnering directly with our CEO and Executive Leadership Team to drive the initiatives that accelerate growth, unlock efficiency, and shape the future of work. You will own the cross-functional operating rhythm that keeps the business moving, and you will do it with the judgment and discretion that comes from being trusted with things that matter.  

This is high-speed, high-visibility, and high-impact—and it demands someone who can take a complex problem, drive it independently through to a decision, and return with a clear output. If that’s the environment where you do your best work, we want to meet you. 

What You’ll Do 

Independent Initiative Ownership 

• Own high-impact strategic initiatives end-to-end—from scoping and alignment through execution and measurable business results. You drive the work, not the calendar. 

• Translate executive priorities into clear, AI-enabled execution plans across functions—with the autonomy to make calls and move without constant direction. 

• Identify execution risks early and deploy mitigation strategies using predictive insights and scenario modeling. Surface what matters; resolve what you can before it lands on the CEO’s desk. 

• Design and track KPIs that tie initiatives directly to revenue, efficiency, and profitability—owning the accountability loop, not just the reporting layer. 

Operating Cadence & Cross-Functional Execution 

• Own and drive the company’s cross-functional operating cadence—QBRs, executive rhythms, leadership forums, and the connective tissue that keeps a fast-moving business aligned and accountable. 

• Orchestrate cross-functional teams to deliver faster, with tighter feedback loops and real-time visibility. You are the force multiplier that unblocks decisions and moves work forward. 

• Build AI-powered operating systems—dashboards, copilots, workflows—that increase the speed and quality of decision-making across the ELT. 

Executive Partnership & Storytelling 

• Partner with the ELT to prepare board materials, CEO updates, and investor narratives using AI-assisted synthesis—turning complex data and dynamics into clear, high-stakes communications. 

• Support the storytelling of the business in a transformative year of AI-native product and company evolution. Help the CEO communicate with clarity, credibility, and confidence internally and externally. 

Change Management & Organizational Navigation 

• Act as a trusted partner to the CEO through periods of organizational change—helping design, sequence, and land transformational decisions in ways that stick. 

• Help the ELT navigate the human side of change: communication, sequencing, stakeholder alignment, and the difference between a decision that’s made and one that’s actually adopted. 

• Serve as a connective bridge across functions—building trust with leaders, surfacing misalignments before they become problems, and modeling the operating culture the company is building toward. 

Judgment, Discretion & Confidentiality 

• Exercise exceptional judgment about what to act on, what to escalate, and what to hold—recognizing that proximity to sensitive information is a trust, not a tool. 

• Handle commercially sensitive data, executive dynamics, personnel decisions, and investor-level information with the discretion expected of someone operating at the most senior level of the organization. 

• Know when to be visible and when to work quietly behind the scenes. Influence without overstepping. Move without leaving a wake. 

What You’ll Bring 

• 5–7 years in strategy consulting, SaaS operations, private equity value creation, or similar high-intensity environments—with a track record of owning outcomes, not just supporting them. 

• Demonstrated ability to take complex, ambiguous workstreams from problem definition through to a clear decision or output—independently, without requiring structure to be built around you. 

• Exceptional judgment: you know what to escalate, what to resolve, and what to hold in confidence. You’ve earned trust by being the person who handles sensitive situations with maturity. 

• Change management experience—you understand that transformation is as much about people and sequencing as it is about strategy. You’ve helped organizations navigate hard decisions, not just document them. 

• Strong operator mindset—you advise and execute, owning outcomes end-to-end. Coordination and synthesis are the floor, not the ceiling. 

• High AI fluency—experience using GenAI, automation tools, and data systems to accelerate workflows and insights. You build with AI, not just use it. 

• Sharp analytical thinking—you translate data into clear decisions and action, and you can hold a financial model, a SaaS metric, and an executive narrative in your head at the same time. 

• Executive presence—you communicate with clarity, influence senior stakeholders, and build trust quickly, even when you’re the least experienced person in the room. 

• Strong financial and SaaS metric literacy—you understand how decisions impact ARR, NRR, EBITDA, and the Rule of 40, not just in theory but in context. 

• A “Love to Win” attitude—you operate from a desire to see success, not a fear of failure. You bring pace, optimism, and resilience to hard problems. 

• Comfort in ambiguity—you bring structure, speed, and focus to complex problems, and you don’t wait to be told what to do next.