Enterprise Account Executive, Expansion (Remote)

OfficeSpace Software•Chicago, IL
•Remote

About The Position

OfficeSpace Software provides an AI operating system for the built world, helping teams plan, connect, and perform in the workplace. The Enterprise Account Executive, Expansion owns growth across a portfolio of high-value strategic clients. The role builds, expands, and protects complex enterprise relationships by developing multi-year expansion strategies aligned with clients’ business priorities. It requires executive-level partnership, strategic deal shaping, platform-level solution selling, and disciplined pipeline and forecast management. The role collaborates with Client Success, Product, and Solutions teams to support adoption, uncover new use cases, and drive measurable client and commercial outcomes. The position is remote.

Requirements

  • 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.
  • Demonstrated ability to build pipeline within existing accounts and develop opportunities independent of contract timing.
  • Strong executive presence and ability to engage and influence C-level stakeholders through business-focused conversations.
  • Strategic thinking and deal-shaping skills, including translating ambiguous client needs into expansion strategies and value propositions.
  • Experience selling platform or multi-product solutions focused on outcomes, ROI, and long-term transformation.
  • Exceptional discovery and multi-threading skills, building relationships across organizational functions and levels.
  • Strong ownership, accountability, and bias toward action and results.
  • Ability to collaborate cross-functionally with Client Success, Product, and technical teams.
  • Comfort working in a high-change, performance-driven environment with expectations for pipeline creation, deal quality, and quota attainment.
  • Intellectual curiosity and business acumen to understand client industries and connect strategic opportunities to OfficeSpace’s platform value.

Responsibilities

  • Own and grow a portfolio of high-value strategic accounts through multi-year expansion strategies aligned with client business priorities.
  • Develop strategic account plans with actionable expansion plays, value hypotheses, timelines, and deal strategies.
  • Proactively create and close pipeline by identifying whitespace and shaping opportunities independently of renewal cycles.
  • Lead complex, multi-threaded sales motions with economic buyers and stakeholders across business, finance, and operations.
  • Sell platform-level solutions by positioning OfficeSpace as a mission-critical operating system that drives measurable business outcomes.
  • Partner with Client Success, Product, and Solutions teams to coordinate account strategy, unlock use cases, and support successful adoption and expansion.
  • Lead executive conversations connecting OfficeSpace capabilities to initiatives such as cost optimization, workforce productivity, and real estate strategy.
  • Maintain disciplined pipeline and deal management, accurate forecasting, and clear progression toward close.
  • Expand deal scope and value toward broader platform adoption across workplaces, assets, and employee experience.
  • Coordinate internal and client stakeholders to deliver client impact and commercial outcomes.

Benefits

  • Comprehensive and competitive benefits packages designed to support health, well-being, and financial security.
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