Top Tech Jobs & Startup Jobs in Chicago, IL

Manage scope, timelines, costs, communications, risks, and customer expectations for multiple SaaS implementation projects. Lead deployment planning, coordinate internal and external stakeholders, establish project controls, support sales and Statements of Work, and partner with cross-functional teams to deliver successful solutions. The role also contributes to implementation methodology improvements and occasionally travels to customer sites for training and relationship building.

Lead and coach a 12-15 person SDR team as a player-coach to meet quotas, run cadence (1:1s, call reviews), hire and ramp reps, own metrics and cross-functional prospecting strategies, and develop promotions into AE/CS/leadership roles.

Lead enterprise sales for OpenGov’s government-focused product suite across an assigned territory. Responsibilities include territory planning, prospecting, relationship management, presentations, product demonstrations, demand generation, contract negotiation, complex deal closure, CRM and sales process management, and quota attainment. The role requires selling software solutions, engaging senior government executives, collaborating with marketing and pre-sales teams, and traveling up to 50%.

Own the full sales cycle from qualified lead through contract signature for OpenGov products serving state and local governments. Manage a defined territory, conduct discovery, deliver demonstrations and proposals, prospect for pipeline, manage opportunities in Salesforce, use MEDDIC, negotiate pricing, achieve quota, and collaborate with solution engineers, marketing, and cross-functional teams. Occasional travel for customer meetings and events is required.

Leads sales efforts for OpenGov products across an assigned territory, including prospecting, territory planning, presentations, relationship management, negotiations, and deal closure. Partners with ERP specialists, marketing, presales, and customer stakeholders to sell complex software solutions to government organizations. Owns pipeline and sales processes, supports demand-generation campaigns, manages executive relationships, and consistently meets or exceeds quota.

Manage end-to-end ERP and software implementation projects for government customers, including requirements gathering, data analysis, platform configuration, administrator training, and deployment support. Serve as the primary technical contact, advise customers on workflow improvements, collaborate across internal teams, gather product feedback, and contribute to implementation best practices and delivery efficiency.

Designs, delivers, and measures organization-wide learning and talent enablement programs, including leadership development, onboarding, manager training, e-learning, workshops, and role-specific education. Partners with subject matter experts, HR business partners, and leaders to identify capability gaps, create scalable learning experiences, facilitate training, manage concurrent projects, and improve outcomes through analytics. The role also applies AI-powered workflows and emerging learning technologies to accelerate content development and increase enablement impact.

Leads a team of quota-carrying Account Executives responsible for full-cycle SaaS sales. Owns bookings, pipeline generation, forecasting, inbound and outbound motions, coaching, recruiting, onboarding, performance management, and cross-functional revenue initiatives. The role emphasizes Salesforce data integrity, sales analytics, AI-enabled productivity, and developing a high-accountability sales culture. Occasional travel of up to 15% is required.

Lead post-sales operations for Professional Services, Customer Support, and Customer Success Engineering. Manage forecasting, utilization, margins, capacity, headcount, systems implementations, AI workflows, metrics, close activities, cross-functional handoffs, and customer experience improvements. Lead a small operations team while partnering with Finance, Sales, R&D, HR, and customer leadership to improve performance and operational execution.

Lead end-to-end payroll and ERP implementations for government customers, manage data requirements and platform configuration, train administrators, design solutions, collaborate cross-functionally, gather product feedback, mentor team members, and drive strategic initiatives to ensure successful deployments and customer adoption.