Top Tech Jobs & Startup Jobs in Chicago, IL

Own retention, adoption, renewals, growth, and outcomes for high-value mid-market SaaS accounts. Build executive relationships, lead success plans and business reviews, identify risks and expansion opportunities, and partner cross-functionally to solve customer challenges. Use AI and customer data to improve account intelligence, planning, workflows, and decision-making while validating outputs through human judgment.

Own technical and solution strategy throughout complex B2B SaaS sales cycles. Lead discovery, solution architecture, tailored demonstrations, technical evaluations, POCs, RFPs, security reviews, and integration discussions. Partner with Account Executives and internal teams to translate customer needs into measurable workplace outcomes. Use and validate AI tools for research, solution design, documentation, and workflow improvement while maintaining technical judgment and customer trust.

Own and expand a portfolio of strategic enterprise accounts through multi-year account planning, executive engagement, pipeline creation, complex deal management, and platform-level solution selling. Build relationships with C-level stakeholders, identify whitespace opportunities, shape value propositions, forecast accurately, and collaborate with Client Success, Product, and Solutions teams to drive adoption, measurable client outcomes, and commercial growth.

Owns enterprise new-logo acquisition from prospecting through contract negotiation and close. Builds pipeline, leads value-based sales cycles with senior stakeholders, delivers product demos, develops proposals and forecasts, maintains Salesforce pipeline hygiene, and partners with Marketing and Business Development. The role requires full-cycle enterprise B2B SaaS selling, quota achievement, AI-assisted sales execution, and the ability to sell workplace, facilities, HR, IT, finance, or real estate solutions.

Leads Deal Operations and GTM Systems, overseeing quoting, pricing, deal desk, renewals, order-to-contract processes, Salesforce and related technology governance, access controls, integrations, automation, and AI-assisted workflows. Partners with Finance and Sales leadership on GTM execution, cash collections handoffs, bookings accuracy, reconciliations, and operational governance. Manages teams, contractors, systems roadmaps, issue triage, and seller productivity initiatives in a remote U.S. SaaS environment.

Own the strategy, vision, roadmap, discovery, execution, and measurement of workplace management and employee engagement products. Partner with Engineering, Design, Research, Marketing, Sales, Customer Success, and Support to identify customer problems, prioritize opportunities, leverage AI-enabled workflows, deliver product capabilities, and measure customer and business outcomes.

Owns the success, retention, renewals, and expansion of strategic enterprise SaaS customers. Builds executive relationships, leads onboarding and adoption, develops success plans, conducts QBRs, analyzes customer health and business outcomes, and partners cross-functionally to resolve issues and influence product direction. Uses AI and customer success platforms to predict risk, automate workflows, identify opportunities, and improve scalable customer success practices.

Leads the B2B SaaS sales development organization, owning inbound and outbound pipeline, strategic ABX, account penetration, forecasting, capacity planning, and SDR performance. Builds and coaches SDR and Senior SDR teams, develops talent pathways, improves funnel conversion, and partners cross-functionally with Sales, Marketing, Revenue Operations, Finance, and Enablement. Designs and governs AI-enabled GTM workflows, measuring their impact on productivity, pipeline, conversion, buyer experience, and acquisition cost.

Own and grow a portfolio of high-value enterprise accounts by developing multi-year expansion strategies, creating pipeline, leading complex multi-stakeholder sales motions, partnering cross-functionally to drive adoption, and positioning OfficeSpace as a platform to deliver measurable business outcomes.

In this role, you will analyze performance across revenue and finance, create models, support forecasts, and generate insights to inform strategic decisions.