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OfficeSpace Software

Executive Chief of Staff

Posted 12 Days Ago
Easy Apply
Remote
Hiring Remotely in United States
5-7 Annually
Senior level
Easy Apply
Remote
Hiring Remotely in United States
5-7 Annually
Senior level
The Director of Strategic Projects leads high-impact initiatives, translating executive priorities into AI-enabled plans, orchestrating teams, and designing systems for efficiency and growth.
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About OfficeSpace: 

OfficeSpace Software provides the leading AI operating system for the built world, that helps teams plan, connect, and perform in the workplace. As a performance-based, PE-backed company, we hire based on merit and a willingness to do what it takes to succeed long-term. You’re a great fit for the role if you’re entrepreneurial, passionate, motivated by building at light speed, and an Agentic AI early adopter. Our world-class teams operate in the US, Canada, and Costa Rica in a culture of trust, respect, growth, and impact.  

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 Director, Strategic Projects 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 lead the initiatives that drive growth, unlock efficiency, and shape the future of work. This is high-stakes, high-visibility, and high-impact. If that's the environment where you do your best work, we want to meet you. 

What You'll Do 

  • Lead high-impact strategic initiatives—from idea to execution to measurable business results 
  • Translate executive priorities into clear, AI-enabled execution plans across functions 
  • Orchestrate cross-functional teams to deliver faster, with tighter feedback loops and real-time visibility 
  • Build AI-powered project operating systems (dashboards, copilots, workflows) to increase speed and decision quality 
  • Partner with ELT to prepare board materials, CEO updates, and investor narratives using AI-assisted synthesis 
  • Support the storytelling of the business in a transformative year with increased AI transformation and AI Native product/company 
  • Identify execution risks early—deploy mitigation strategies using predictive insights and scenario modeling 
  • Design and track KPIs that tie initiatives directly to revenue, efficiency, and profitability 
  • Act as a strategic force multiplier—step into critical conversations, unblock decisions, and move work forward 

What You'll Bring 

  • 5–7 years in strategy consulting, SaaS operations, private equity value creation, or similar high-intensity environments 
  • Proven track record of driving complex, cross-functional initiatives to measurable outcomes 
  • Strong operator mindset—you advise and execute, owning outcomes end-to-end 
  • High AI fluency—experience using GenAI, automation tools, and data systems to accelerate workflows and insights 
  • A "Love to Win" Attitude – You operate from a desire to see success and win, not a fear of failure or loss 
  • Ability to design and orchestrate AI-assisted execution systems (not just use tools) 
  • Sharp analytical thinking—translate data into clear decisions and action 
  • Executive presence—communicate with clarity, influence senior stakeholders, and build trust quickly 
  • Strong financial and SaaS metric literacy—understand how decisions impact growth and efficiency 
  • Comfort in ambiguity—you bring structure, speed, and focus to complex problems 

 

Why OfficeSpace?

  • High-Performance Culture: At OfficeSpace, we believe in the power of accountability, focus, and drive. Our A-Player team members work together to deliver measurable, meaningful results. We recognize and reward those who push boundaries and achieve excellence.
  • Ownership and Accountability: We trust our employees to take full ownership of their roles, providing the autonomy to innovate and the support to succeed. We seek individuals who are self-motivated and thrive in an environment where they can drive impactful outcomes.
  • Technology-Forward: As a company invested in cutting-edge technology, we integrate AI and other advanced solutions across our platform to enhance productivity, customer experience, and process efficiency. Our team members are excited by the potential of AI and proactively explore ways it can drive our success.
  • Growth Mindset: Continuous learning and improvement are integral to our culture. We encourage our team to embrace challenges, seek knowledge, and develop both personally and professionally.
  • Innovation and Agility: We foster a dynamic, fast-paced environment where fresh ideas and bold solutions are celebrated. We embrace change and thrive on turning challenges into opportunities, with a team that is agile, proactive, and resilient.
  • Collaborative, Results-Driven Environment: We value purposeful collaboration that leads to shared success and stronger results. While our team members are independent, they recognize the value of working together to drive our mission forward.
  • Competitive Benefits and Rewards: OfficeSpace offers comprehensive and competitive benefits packages globally, designed to support our team’s health, well-being, and financial security. We invest in our people so they can excel.
    OfficeSpace is committed to building and promoting a diverse workforce and celebrates the unique qualities that individuals of various backgrounds and experiences offer. We are committed to basing all employment-related decisions upon valid job-related factors without regard to race, color, sex (including pregnancy, sexual orientation, and gender identity), age, religion, national origin, genetic information, military status, veteran status, physical or mental disability, or any other status protected by law. 

Top Skills

AI
Automation Tools
Data Systems
Genai

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