Enterprise Account Executive, Expansion; Remote

Office Space 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.

You own growth at the highest level. As an Enterprise Account Executive
- Strategic, you build, expand, and protect strategic relationships across complex organizations with our highest value clients. You operate as a value architect, and executive partner to drive strategic and transformational client value - using data, AI, and sharp commercial discipline to grow enterprise accounts.

• Own and grow a portfolio of high-value strategic accounts by developing and executing multi-year expansion strategies aligned to each client's business priorities.
• Develop and execute strategic account plans that translate client priorities into actionable expansion plays with clear value hypotheses, timelines, and deal strategies.
• Create and close pipeline proactively - not tied to renewal cycles - by identifying whitespace, shaping opportunities, and aligning to executive-level priorities within your accounts.
• Lead complex, multi-threaded sales motions by engaging economic buyers and key stakeholders across business, finance, and operations to build consensus and urgency.
• Sell platform-level solutions, not product features, positioning Office Space as a mission-critical operating system that drives measurable business outcomes.
• Partner closely with Client Success, Product, and Solutions teams to orchestrate account strategy, unlock new use cases, and ensure successful adoption that fuels expansion.
• Drive executive conversations that connect Office Space capabilities to enterprise-level initiatives such as cost optimization, workforce productivity, and real estate strategy.
• Operate with rigor and discipline in pipeline and deal management, maintaining high-quality opportunities, accurate forecasting, and clear progression toward close.
• Continuously expand deal scope and value, moving beyond initial use cases to broader platform adoption across workplaces, assets, and employee experience.
• Act as the quarterback of your accounts, ensuring alignment across all internal and client stakeholders to deliver both client impact and commercial outcomes.

• Bachelor's degree.
• 5-10+ years of SaaS sales experience across Mid-Market and Enterprise segments
• Proven experience in complex B2B or enterprise sales, with a track record of creating and closing large, multi-stakeholder deals (not just managing renewals or transactional upsells).
• Demonstrated ability to build pipeline within existing accounts, identifying and developing opportunities independent of contract timing.
• Strong executive presence, with the ability to engage and influence C-level stakeholders (CFO, COO, CIO) through business-focused conversations.
• Strategic thinking and deal-shaping capability, including the ability to translate ambiguous client needs into clear expansion strategies and compelling value propositions.
• Experience selling platform or multi-product solutions, with a focus on outcomes, ROI, and long-term transformation rather than features.
• Exceptional discovery and multi-threading skills, consistently building relationships across functions and levels within an organization.
• High level of ownership and accountability, operating with a "CEO of the account" mindset and a bias toward action and results.
• Ability to collaborate cross-functionally, leveraging Client Success, Product, and technical teams to drive both adoption and expansion.
• Comfort operating in a high-change, performance-driven environment, with clear expectations around pipeline creation, deal quality, and quota attainment.
• Intellectual curiosity and business acumen, enabling you to understand client industries, uncover strategic opportunities, and connect them to Office Space's platform value.

At Office Space, 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…