Top Sales Jobs in Chicago, IL

Manage inbound homeowner leads through the full sales cycle for Hometap's home equity investment: qualify and educate homeowners, maintain pipeline in Salesforce and Hometap's Hub, coordinate with internal teams, collect documentation, close deals, and meet monthly and quarterly sales targets while ensuring regulatory compliance.

Leads six frontline managers and 30+ Account Executives in expanding existing enterprise accounts, driving net retention, cross-sell adoption, and multi-year renewals. Coaches teams on expansion selling, executive reviews, relationship development, forecasting, and account health. Sponsors major renewals and complex negotiations while partnering with Customer Success, Professional Services, and Product teams. Requires extensive software subscription sales leadership experience, strong SaaS and retention-metric expertise, and executive communication skills.

Leads North American new-logo sales by managing, coaching, and recruiting 6–7 Account Executives. Drives net-new ARR growth, enterprise market penetration, pipeline generation, complex contract negotiations, and quota attainment across commercial and mid-market segments. Partners with Marketing, Product, and Sales Engineering to refine go-to-market strategy, accelerate deal velocity, and secure strategic enterprise customers. Requires executive-level communication, SaaS sales expertise, and experience closing seven-figure contracts.

Lead and build Toast Retail’s Mid-Market sales function from the ground up. Manage and coach Account Executives while personally closing complex grocery, liquor, and convenience retail deals. Develop repeatable sales processes, qualification frameworks, business cases, proposals, forecasting practices, and competitive positioning. Partner cross-functionally with Product, Marketing, Enablement, Finance, Deal Desk, and Onboarding to support enterprise implementations and product improvements. Hire and develop a high-performing team, establish benchmarks, and transition from a player-coach role to full team leadership.

Own revenue and quarterly quota for the West territory covering Oregon, Idaho, Montana, and Hawaii. Build and expand relationships with benefits brokers, consultants, general agents, and employers in the 1,000–9,999 employee market. Develop strategic advisor partnerships, lead complex cross-functional deals, close new business, and shape regional sales strategy with enterprise and account teams.

Provides technical product expertise and presentations to prospective customers, helping improve their security posture and positioning Huntress solutions. Partners with Sales, Marketing, Support, and Engineering to identify customer needs and product improvements. Reviews security issues with technical teams, supports MSP and VAR customers, and travels approximately 25% to meet customers.

The Sales Development Representative is responsible for qualifying new revenue opportunities, engaging with potential clients, and meeting daily performance metrics while representing the company at trade shows.

Support and scale enterprise sales operations by improving processes, systems, tooling, analytics, and seller workflows. Partner with sales leadership, Salesforce Systems, and Revenue Operations teams to prioritize requests, redesign processes, define requirements, conduct UAT, maintain operational metrics, and implement scalable solutions. Lead complex cross-functional initiatives that improve sales outcomes, retention, expansion, and efficiency while translating policies and processes into field guidance.

Leads sales strategy and account planning for UL products and services in the retail softlines sector. Manages existing relationships, renewals, specialty-product opportunities, and new-logo sales from prospecting through close. Builds pipelines, conducts discovery, develops proposals, coordinates technical resources, and transitions closed deals to fulfillment teams. Provides expert guidance to account managers and contributes to multi-year growth plans.

Manages Buick and GMC dealership relationships across an assigned territory. Responsibilities include consulting dealers to achieve sales goals, analyzing sales and market data, supporting marketing and product launches, monitoring training and compliance, managing vehicle and parts inventory, improving customer satisfaction, resolving customer issues, and increasing vehicle and accessory sales. The role is field-based, requires frequent travel, dealership engagement, regular vehicle operation, and relocation or residence within the approved territory.

Manages Buick GMC dealership relationships across the Syracuse territory. Responsibilities include visiting dealers, supporting sales objectives, analyzing sales and market data, coordinating marketing and product launches, monitoring training and compliance, assisting with inventory management, resolving customer issues, and identifying revenue opportunities. The role is field-based, requires frequent travel, regular vehicle operation, and residence or relocation within the assigned territory.

Drive pipeline growth through outbound prospecting and inbound lead engagement, targeting senior decision-makers. Collaborate with sales and marketing, research accounts, run multi-channel campaigns, log activity in Salesforce, and use tools like LinkedIn Sales Navigator, ZoomInfo, Gong, and Winmo to generate meetings and qualified opportunities.

Conduct outbound and inbound sales outreach, qualify leads through discovery, maintain CRM records, assist with quotes and proposals, support product-focused solution selling, collaborate with field teams, track sales metrics and campaign engagement, and participate in ongoing training to meet activity and revenue targets.

Lead go-to-market and account strategy for Moveworks on the ServiceNow platform. Coach account teams, support solution visioning, align territory and account plans to drive specialty-solution wins, partner with specialists and customers, and help quantify ROI of digital transformation.

Lead territory strategy and support account teams to position and win Moveworks solutions on the ServiceNow platform. Advise customers on digital transformation value, coach AEs/ADRs/ACEs, align roadmap with specialists, and help manage sales cycles. Allocate time based on territory needs and celebrate wins.

The Sales Operations Manager will optimize processes, lead cross-functional programs, and improve sales efficiency to drive revenue growth for Samsara's Enterprise Sales organization.

Owns direct enterprise sales across a national territory of education employers, including universities, school districts, benefits pools, and associations. Manages prospecting, quotas, pipelines, and end-to-end RFP pursuits involving consultants, procurement, finalist presentations, and governance approvals. Builds strategic relationships with education benefits consultants, pool administrators, and benefits directors while communicating competitive value propositions. Requires deep health benefits and education-sector sales expertise, enterprise selling experience, data literacy, and sales process development skills.

Leads and develops a team of Account Managers, Account Executives, and Client Executives. Responsibilities include hiring, coaching, sales planning, territory assignment, customer and partner engagement, performance management, and achieving segment sales and profit goals. The role analyzes sales data, manages operating plans, supports customer outcomes, and drives team adoption of AI-enabled practices. Travel to customer meetings may reach 20%.

Lead and coach a Mid-Market Account Executive team to meet quota, hire and ramp talent, enforce sales process, forecast performance, identify risks and collaborate cross-functionally to improve sales outcomes.

Own the technical pre-sales cycle for strategic public-sector and enterprise customers. Partner with sales executives on complex deals, align customer requirements with IoT hardware, SaaS dashboards, APIs, integrations, and cloud solutions, and conduct proof-of-concept hardware deployments. Build customer relationships, develop business justifications, mentor sales engineers, and support technical enablement. The remote role covers the Eastern Time Zone Midwest region and requires approximately 50% travel.

The Sales Engineer supports mid-market sales by delivering technical discoveries, product demonstrations, value assessments, proofs of concept, and deployment plans. Responsibilities include explaining IoT solutions, advising customers on hardware installation and integrations, scripting against open APIs, consulting on business transformation, and translating customer feedback to product and sales teams. The role is remote within the Midwest and requires travel up to 50%.

Leads the division’s marketing and sales strategy, overseeing sales teams, advertising sales, customer relationships, market analysis, growth opportunities, pricing, forecasts, and strategic execution. Builds and maintains client accounts, directs internet advertising sales, develops policies and objectives, influences executive leadership, and manages multiple teams through managers and team leaders.

Support Treasury Management Officers by preparing client proposals, performing cost/benefit and profitability analyses, creating pitchbooks and account plans, understanding clients' cash management needs, coordinating with product partners, managing pipeline, and ensuring accurate implementation, pricing, and billing.

Develop new payments business from under-penetrated domestic bank clients by understanding client needs, delivering treasury, cash management, FX, receivables and blockchain solutions, building pipeline, driving cross-sell with coverage teams, and meeting sales and financial targets through client engagement and strategic account planning.

Support Payments Sales Managers by managing client portfolios, identifying new business opportunities, developing account plans, coordinating onboarding/KYC and internal partners, analyzing transaction data for pricing/billing inefficiencies, and driving relationship initiatives across treasury, operations, risk, and legal.