Business Development Manager

4 days ago

Chicago IL, Cook County, IL; Illinois, United States Total Parking Solutions, LLC. Full-time

We're hiring a Business Development Manager to own sales at Total Parking Solutions. You'll be our only dedicated salesperson, working directly with the CEO to grow our footprint of municipal, institutional, and government customers. Your core territory is the Midwest, with remote coverage of our Florida market and the flexibility to pursue new markets and opportunities as they come up. You'll run the full sales cycle for parking terminal installations and cross-sell associated products —WebOffice software, service & maintenance agreements, and partner-enabled offerings like mobile payment apps and digital parking permits — primarily into new accounts. This role is a fit for someone with 2–5 years of B2B or B2G sales experience — you don't need a background in parking or municipal government specifically, but you should be comfortable navigating longer sales cycles (RFPs, board approvals, procurement processes) and building trust with public-sector buyers. We'll train you on our products, our municipal sales process, and the parking industry. Because you're the only dedicated sales hire, you'll need to be comfortable working independently — managing your own pipeline, priorities, and travel schedule without a sales team around you, while staying closely aligned with the CEO on strategy and results. This is a ground-floor opportunity for someone who wants to build a career with a small, growing business: you'll have real input into how we build out our sales process and tools, and the chance to grow into a sales leadership role as Total Parking Solutions scales.

Key Responsibilities
Own sales for TPS as the company's only dedicated salesperson, managing your own territory, pipeline, and priorities Manage a flexible, multi-state territory — core markets across the Midwest, our Florida book of business, and new markets as opportunities arise Run the full sales cycle: prospecting, cold calling/outreach, needs assessment, proposal development, RFP response support, contract negotiation, and close Sell new parking terminal installations and cross-sell associated products — WebOffice software, service & maintenance agreements, and partner-enabled offerings such as mobile payment apps and digital parking permits Build and maintain relationships with municipal decision-makers (public works, finance, parking authorities, city administrators) Partner with the operations and service teams to ensure smooth handoff from signed contract to installation Maintain accurate pipeline, forecast, and account records in the company CRM Represent TPS at municipal association conferences, trade shows, and industry events as needed Stay current on product updates, competitive landscape, and municipal procurement trends Provide accurate, timely pricing and proposal documents in coordination with the CEO Help shape TPS's sales process, tools, and — eventually — team as the business grows What We're Looking For Required: 2–5 years of sales experience, ideally B2B, B2G, or another relationship-driven, longer-cycle sales environment Track record of managing a pipeline and closing deals against a quota Comfortable working independently as the company's only dedicated salesperson — self-directed, organized, and able to manage a multi-month sales cycle without close daily supervision Comfortable with public-sector sales processes (RFPs, procurement, board/council approvals) — or a fast learner if new to this Strong written and verbal communication skills; able to present confidently to municipal officials and boards Valid driver's license and ability to travel regularly across a multi-state territory (including occasional overnight travel for conferences) Proficiency with CRM tools, Microsoft Office/Google Workspace, and basic proposal/pricing documents Nice to Have: Experience selling to municipalities, government agencies, or other institutional/public-sector buyers Background in parking, transportation, smart city infrastructure, or related equipment/technology sales Existing relationships with Midwest or Florida municipal contacts Familiarity with recurring-revenue or SaaS-attach sales model Interest in growing into a sales leadership role as the team expands Compensation Compensation is structured to reward new equipment sales, the recurring revenue you build in your territory, and cross-sold partner products: $55,000 – $70,000, based on experience On-Target Earnings (OTE) $80,000 – $100,000+ (base + commission at target performance) Commission is not capped Other Mileage/gas reimbursement for field travel; standard employee benefits (including healthcare and 401k) Final compensation plan details, quota, and territory are formalized in the employment offer and commission agreement. Training and Support Structured onboarding covering our product lines, municipal sales process, and CRM/tools Shadowing with the CEO and the service/operations team