Top Tech Jobs & Startup Jobs in Chicago, IL

Drive high-volume outbound prospecting to build and qualify an acquisition pipeline. Engage business owners and founders, schedule introductory calls, maintain CRM records, follow up across long sales cycles, gather key business information, and support deal flow. Attend industry events as needed.

The Digital Marketing Manager will oversee digital strategies and execution for HOA Sales, focusing on web presence, SEO/AEO, content distribution, and lead generation.

Manage day-to-day HR administration for ~100–115 employees: Rippling system administration, onboarding/terminations, benefits administration, multi-state payroll and compliance, audit coordination, and building automated workflows and HRIS processes to reduce manual work.

Manage multi-state business and payroll registrations, ensure regulatory compliance, maintain audit-ready records, track deadlines, support administrative tasks, coordinate vendors and property maintenance, process invoices, and assist cross-functional teams with operational and compliance initiatives.

Manage full lifecycle of 4-5 concurrent M&A deal transitions on a 60-day close cycle. Serve as primary contact for sellers and clients, drive timelines, coordinate communications, track data transformation requests with Data & Automation, maintain deal records in PM systems, escalate issues, and contribute to process and SOP improvements to scale operations.

Hands-on leader who will design and build a proprietary automation tool, own multi-system data mapping and migrations, define data standards, manage a Data Analyst, maintain a master data dictionary and integration map, QA automation output, and translate operational requirements into technical solutions to streamline deal transitions.

The ERP Systems Manager will assess and improve ERP implementations across member companies, develop playbooks, and train staff on optimized workflows.

The Business Development Representative will generate leads and nurture client relationships in the real estate market, contributing to sales goals by conducting market research and outreach.

Manage full sales cycle to win HOA and property management clients: prospecting, presentations, negotiating contracts, onboarding coordination, CRM maintenance, and meeting sales targets while collaborating with internal teams and staying current on industry trends.