Strategic Account Executive, Expansion
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:
You own growth at the highest level. As a Client Executive – Enterprise, 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.
What You Will Do
- 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 OfficeSpace 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 OfficeSpace 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.
What You’ll Bring:
- 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 a