Top Tech Jobs & Startup Jobs in Chicago, IL

Own net-new enterprise sales across public-sector organizations in the Western United States. Develop territory strategy, generate pipeline, engage senior government executives, navigate complex procurement and contracting processes, and close strategic software agreements valued at $500,000 or more annually. Sell UKG’s cloud-based HCM and workforce management solutions while coordinating internal teams and partners, managing long sales cycles, maintaining accurate forecasts, and achieving revenue targets.

Serve as a trusted technical advisor to customers and prospects by uncovering business needs, designing tailored HR technology solutions, delivering product demonstrations and presentations, and partnering with sales teams. The role requires expertise in UKG’s HR, payroll, and workforce management products, strong consultative communication skills, project prioritization, and travel of up to 25%.

Drive net-new logo sales of HCM and payroll SaaS solutions to mid-market and enterprise organizations. Exceed quotas, prospect within an assigned territory, present solutions to decision-makers, develop proposals, understand customer business outcomes, and maintain knowledge of HCM technology, competitors, and industry trends. The role requires proven success selling HRMS/payroll solutions and strong strategic sales, communication, and presentation skills.

Leads new-logo sales by managing Account Executives, coaching performance, supporting sales strategy, driving quota attainment, developing talent, and fostering a positive team environment. Partners with sales leadership to improve processes, motivate representatives, and achieve team goals. Requires demonstrated quota achievement as an individual contributor and at least 2–5 years of closing-sales experience, with payroll/HCM SaaS experience preferred.

Provides independent employee relations guidance to leaders and HR partners, managing matters involving performance, conduct, corrective actions, separations, and workplace concerns. Advises on risk-informed employment decisions, coaches leaders through difficult situations, partners with Legal and HR stakeholders, supports organizational changes, and identifies trends to improve processes, consistency, compliance, and employee experience.

Serves as the primary finance partner to GTM and Marketing leadership. Leads headcount planning, budgeting, forecasting, expense management, and financial modeling. Analyzes performance against plan, provides strategic recommendations, supports annual planning and monthly close, and improves reporting processes. Partners with Corporate FP&A, Sales Finance, HR, and business leaders on resource allocation, cost optimization, and operational alignment.

Develops customer-specific business cases that quantify the value and ROI of UKG workforce management and human capital management solutions. Conducts research, interviews, surveys, discovery sessions, and data analysis; translates operational insights into value assessments and recommendations; presents findings to customers, prospects, executives, and internal teams; and collaborates with Sales, Marketing, Product, and Customer Success.

Leads FP&A activities for G&A functions, including annual planning, forecasting, financial reviews, long-range planning, financial modeling, investment analysis, and executive reporting. Partners with business leaders to evaluate resource allocation, risks, opportunities, and strategic initiatives. Drives process improvement through automation, AI-enabled tools, and Power BI while delivering actionable insights and supporting data-driven decisions.

Manages multiple HR projects, primarily related to mergers and acquisitions. Responsibilities include defining scope, building timelines, coordinating cross-functional teams, monitoring progress and risks, leading meetings, communicating updates, measuring performance, and contributing to HR PMO best practices.