Top Tech Jobs & Startup Jobs in Chicago, IL

Investigate, evaluate, and resolve property and casualty claims end-to-end. Review policies for coverage, negotiate settlements, maintain accurate documentation, communicate with stakeholders, support legal/compliance activities, and identify process improvements to meet productivity and turnaround targets.

Build and maintain scalable backend microservices and developer-facing APIs, lead projects end-to-end, collaborate with product and engineering teams, design secure/versioned APIs, and manage cloud infrastructure using IaC.

Provide administrative and operational support to Partner Success, handle inbound tickets within SLAs, run group retrainings, schedule onboarding and partner meetings, maintain HubSpot records, perform audits, and escalate complex or high-risk issues with recommendations.

Lead multiple engineering teams and Engineering Managers to deliver scalable landlord-facing products. Drive technical strategy, architecture, execution discipline, and product partnership. Improve delivery predictability, team health, hiring, and leadership development to ensure high-impact, reliable systems that support multifamily operators and landlord workflows.

Lead mid-market multifamily sales across a large West Coast territory, acquire new logos, generate pipeline via events and outreach, build buying committees, consultatively sell and cross-sell products, forecast to quarterly OKRs, partner with account managers for rollouts, maintain HubSpot records, represent the company at tradeshows, and travel roughly one week per month.

Own full-cycle sales on a named book while driving adoption of TheGuarantors products. Deliver virtual/in-person training, support leasing teams, monitor referral pipelines, collect product feedback, analyze client performance, and collaborate with Account Management and GTM teams to increase usage and expand business.

Own full-cycle sales for a named book of multifamily property management clients: drive account engagement strategy, demos, launches, QBRs, and growth. Coordinate with Partner Success, GTM, Marketing, and Customer Success, manage pipeline and performance data, handle objections, ensure regulatory compliance, and improve pitch processes while meeting quota and delivering accurate, timely account management.

Own full-cycle B2B sales to acquire net-new multifamily property management clients: prospect, conduct discovery, build demos, close deals, support account launches, represent the company at events, track pipeline and competitive intelligence, and partner with GTM, Account Management, Marketing, and Customer Success to meet quota and improve sales processes while maintaining regulatory compliance.