Enterprise Account Executive, Expansion (Remote)

OfficeSpace Software•Chicago, IL

6d•Remote

About The Position

OfficeSpace Software is seeking an Enterprise Account Executive, Expansion, to own growth across a portfolio of high-value strategic accounts. The role develops and executes multi-year expansion strategies aligned with clients’ business priorities, creates new opportunities within existing accounts, and closes complex enterprise deals. The position focuses on selling platform-level solutions and measurable business outcomes, while building executive relationships and coordinating internal and client stakeholders to drive adoption, expansion, and commercial results.

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, including creating and closing large, multi-stakeholder deals.
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 capability, including translating ambiguous client needs into expansion strategies and value propositions.
Experience selling platform or multi-product solutions with a focus on outcomes, ROI, and long-term transformation.
Exceptional discovery and multi-threading skills, with an ability to build relationships across functions and levels.
High ownership and accountability, with a bias toward action and results.
Ability to collaborate across functions and work with Client Success, Product, and technical teams to drive adoption and expansion.
Comfort operating in a high-change, performance-driven environment with expectations around pipeline creation, deal quality, and quota attainment.
Intellectual curiosity and business acumen to understand client industries and connect strategic opportunities to platform value.

Responsibilities

Own and grow a portfolio of high-value strategic accounts through multi-year expansion strategies aligned with client priorities.
Develop strategic account plans with actionable expansion plays, value hypotheses, timelines, and deal strategies.
Proactively create and close pipeline within existing accounts by identifying whitespace and opportunities beyond renewal cycles.
Lead complex, multi-threaded sales motions and build consensus with economic buyers and stakeholders across business, finance, and operations.
Position OfficeSpace as a mission-critical platform that drives measurable business outcomes, rather than selling product features.
Partner with Client Success, Product, and Solutions teams to coordinate account strategy, unlock use cases, and support adoption that fuels expansion.
Lead executive conversations connecting OfficeSpace capabilities to initiatives such as cost optimization, workforce productivity, and real estate strategy.
Manage pipeline and deals with rigor, maintaining opportunity quality, accurate forecasts, and clear progression toward close.
Expand deal scope and platform adoption across workplaces, assets, and employee experience.
Coordinate internal and client stakeholders to deliver client impact and commercial outcomes.