Top Tech Jobs & Startup Jobs in Chicago, IL

Serve as primary contact for new clients during first 30-90 days, deliver virtual one-on-one training, identify needs and proactively resolve roadblocks, maintain accurate client records across platforms, and drive adoption and long-term retention through relationship-building and consultative support.

Respond to inbound leads rapidly, qualify prospects, book high-quality demos, and maintain CRM hygiene. Collaborate with Sales and Marketing to nurture leads, run re-engagement campaigns, track metrics, and iterate on messaging to convert interest into pipeline and revenue.

Own outbound prospecting and cold calling to qualify landscape, tree care, and snow removal operators for Sales Executives. Build relationships, track KPIs in CRM, collaborate with SDR Manager and sales, and represent the company at quarterly trade shows across the US and Canada.

Call into existing customers to identify and qualify upsell and cross-sell opportunities (focus on invoicing and payments), drive product adoption, book expansion meetings, run high-volume phone-first outreach supported by email sequences, track activity and pipeline in Salesforce, partner with Customer Success and Payments for warm handoffs, handle objections, and share messaging feedback to improve expansion performance.