Top Vice President of Sales Jobs in Chicago, IL

Senior revenue leader responsible for driving national new-business growth across enterprise, RFP-driven, and strategic LTL opportunities. Owns a national pipeline, leads full sales cycles, develops deal strategies, supports office-based teams with enablement and coaching, manages RFPs, and collaborates cross-functionally to ensure competitive, executable solutions and successful onboarding.

Lead commercial growth and GTM for Automobile Physical Damage (APD) solutions, owning revenue and adoption targets. Drive enterprise sales, build and scale a specialist APD sales team, partner cross-functionally with Product, Engineering, Marketing, and Customer Success, and strengthen executive client relationships to deliver measurable cost, accuracy, and cycle-time improvements.

Lead net-new enterprise sales for Workday professional services, partnering with Workday’s sales organization on co-selling and pipeline development. Manage concurrent sales cycles, forecasting, territory leads, quota performance, estimates, statements of work, contracting, and customer relationships. Support field marketing activities, report sales progress, and coordinate internal teams while traveling up to 50% to customer and Workday locations.

Lead medium-enterprise customer-base sales across assigned industries and territories. Partner with Workday field sales teams to generate pipeline, develop co-selling strategies, manage concurrent sales cycles, maintain accurate forecasts, negotiate statements of work and contracts, estimate services, achieve annual quotas, and report sales progress. The role also supports field marketing activities and requires travel to customer and Workday locations up to 50%.

Leads Horace Mann’s national Exclusive Agent sales channel across insurance and financial services. Owns sales performance, profitable growth, retention, productivity, agent recruiting and engagement, territory strategy, channel modernization, compensation, and agency economics. Builds and develops a distributed field leadership organization, establishes performance systems, drives CRM and digitally enabled selling, and partners cross-functionally to align enterprise priorities and strengthen service to educators.

Own and scale enterprise go-to-market strategy across sales, offerings, strategic partnerships, pipeline, bookings, and revenue. Personally lead complex consulting and technology-services pursuits while building a repeatable sales motion, developing differentiated offerings, establishing partner-led strategies, improving CRM and forecasting discipline, and creating scalable operating processes. The role initially combines hands-on enterprise selling with leadership, coaching, executive reporting, and organizational design.

Lead buildout of the sales organization: configure CRM, define pipeline and outreach cadences, create sales playbook and market collateral, hire and manage sales reps, set quotas and territories, run pipeline reviews, and support deal closures and handoffs to customer success.

Lead and grow a Central-region mid-market sales organization targeting employers (50–9,999 lives). Manage Regional Directors and AEs, set and execute sales strategy, develop broker/partner relationships, hit revenue targets, collaborate cross-functionally, and ensure compliance. Coach and scale a high-performing team focused on measurable impact and adoption of AI-enabled tools.

Lead and scale West-region employer sales for mid-market accounts by managing Regional Directors and Account Executives, building broker partnerships, executing sales strategies, tracking performance, and ensuring compliance. Drive revenue growth, coach a high-performing team, and collaborate cross-functionally to meet company objectives.

Lead and manage Regional Directors and Account Executives across the East region to drive sales to mid-market employers (50–9,999 lives). Develop and execute sales strategies, build broker and partner relationships, identify new business, monitor performance, and collaborate cross-functionally to meet revenue targets while ensuring compliance and team accountability.

Leads digital advertising sales strategy and revenue growth for the Central region. Responsibilities include managing agency and brand relationships, achieving revenue targets, developing go-to-market and staffing plans, directing the sales process, hiring and motivating sales professionals, presenting marketing solutions, and collaborating with product marketing, research, operations, and account management teams.

Lead Midi Health’s commercial sales organization across payer and employer sales, alliances, client success, and sales operations. Own commercial strategy, revenue growth, retention, forecasting, pipeline rigor, and team development. Build scalable go-to-market capabilities, manage complex enterprise partnerships, engage senior healthcare stakeholders, and report performance to executive leadership and the board.

Lead North America Higher Education sales to drive bookings, new customer acquisition, account expansion, and strategic partnerships. Build and coach a high-performing sales leadership team, own forecasting and pipeline discipline, cultivate executive customer relationships, partner cross-functionally on renewals and product-market fit, and execute go-to-market strategies to scale revenue and improve customer outcomes.

Lead enterprise sales for Linqia's creator marketing platform to Fortune 1000 brands and agencies. Own full sales cycle, build $1M+ deals, develop strategic client relationships, mentor team members, drive quota achievement, and leverage data-driven insights and social best practices. Role requires travel and collaboration across functions while building pipeline and closing large multi-year contracts.

Leads the Tax division sales organization, owning revenue, growth, profitability, market share, strategy, forecasting, partner relationships, and strategic account management. Recruits and develops sales personnel, negotiates contracts, represents the company at industry events, and collaborates cross-functionally on products, customer experience, marketing, compliance, and go-to-market initiatives. Uses Salesforce, performance metrics, and market insights to improve pipeline visibility and advise senior leadership.

Lead US sales and expansion efforts as a hands-on player-coach: build predictable pipeline, personally close strategic deals, grow Net Revenue Retention with CSMs, align Sales with Product/Engineering/CS, scale partner-led opportunities, and continuously optimize sales processes. Frequent travel and cross-functional influence in a matrix organization required.

The VP of Franchise Sales is responsible for driving franchise sales growth, managing the sales process, negotiating agreements, and maintaining relationships with franchisees.

Lead and scale the mid-market sales organization for a high-growth SaaS HR platform. Develop and execute sales strategies, manage and coach account executives and sales leaders, drive pipeline management and forecasting, partner cross-functionally to expand accounts, and represent the company at industry events to meet revenue targets.

Lead P&L for Sales & Marketing, build and coach a senior quota-carrying sales team, execute aggressive go-to-market and product launches for ambulatory EHR, embed AI across commercial operations, drive data-driven pipeline and forecasting, own marketing/brand strategy, and partner with product for beta programs and customer feedback.

Senior leader owning broker and consultant distribution for Pivot Health: build and scale sales and account management teams, drive new business with agents/FMOs, establish SLAs and performance metrics, improve broker retention and experience, align distribution strategy with product and operations, and report pipeline and forecasts to executive leadership.

The VP, Sales & Strategic Partnerships will lead sales strategies, manage key accounts, and drive business growth through partnerships. Responsibilities include implementing sales plans, overseeing business development, improving sales operations, and collaborating with cross-functional teams to meet company objectives.

Lead GTM and market-building for Traders, Renewable Developers/IPPs, Data Centers, and Consultants across the Americas. Own segment strategy, pipeline creation, ARR targets, and forecast accuracy. Manage six Account Executives and align Customer Success for adoption and expansion. Build value propositions, partner ecosystems, sales playbooks, and drive new-logo acquisition and net revenue retention through cross-functional execution.

Lead U.S. commercial sales and go-to-market strategy for CAR-T therapies. Build and scale a specialty sales organization, drive launches and market penetration, manage field teams, collaborate cross-functionally on access and site readiness, and use analytics to monitor KPIs and optimize performance.

The role involves leading sales strategies and generating business with fintech organizations, focusing on closing significant deals and managing sales pipelines.

Leads global enterprise sales strategy across renewals, expansions, upsells, strategic accounts, and partnerships. Builds C-suite relationships, manages complex multi-country engagements, drives forecasting and revenue accountability, coaches sales teams, and improves client experience. Partners cross-functionally to connect workplace culture and employee experience solutions to measurable business outcomes. Oversees account governance, risk mitigation, negotiations, pricing, executive communications, escalations, and strategic growth opportunities.