Top Tech Jobs & Startup Jobs in Chicago, IL

Manage post-sale commercial relationships for a global SaaS customer base, driving net revenue retention through add-on adoption and upsells. Execute high-volume outbound outreach, manage pipeline and forecasting in Salesforce, lead discovery calls and demos, structure deals and renewals, and collaborate cross-functionally to inform product and GTM strategy.

Manage and grow revenue from existing Hostaway customers by selling add-ons (e.g., Dynamic Pricing, Smart Locks, QuickBooks Online). Conduct high-volume outbound outreach, run demos, qualify opportunities, handle objections, negotiate and close deals. Maintain accurate Salesforce pipeline, meet monthly/quarterly quotas, and partner with Customer Success to identify expansion opportunities.

Lead and scale a remote North America sales team of Account Executives for a SaaS vacation-rental platform. Drive revenue, set and monitor KPIs, coach reps, refine sales strategy, manage pipeline and forecasts, collaborate cross-functionally, optimize processes, and act as market expert for NAM.

Own the full outbound-focused B2B SaaS sales cycle for North America: build strategic account plans, manage relationships with decision-makers, exceed revenue targets, pursue upsell/cross-sell, keep accurate CRM records, and collaborate with marketing, product, and customer success to support regional expansion.