Top Sales Jobs in Chicago, IL

Leads and scales Square’s Central Region Field Sales organization, managing Sales Managers and Territory Account Executives. Responsibilities include territory and go-to-market strategy, pipeline and KPI management, field coaching, consultative selling, product expertise, team development, cross-functional collaboration, and regional revenue growth. The role builds a competitive, accountable, high-performing sales culture while representing Square with local business leaders and partners.

Leads New Relic’s AMER partner sales organization, building a channel sales team and driving partner-sourced revenue through VARs, GSIs, MSPs, and regional partners. Coaches sales teams, orchestrates partner-led deals, strengthens alignment with direct sales, expands partner relationships, and improves pipeline conversion and quota attainment. Requires extensive North American and LATAM partner networks, proven channel deal-making experience, resilience in ambiguous environments, and deep observability, APM, or log management expertise.

Generates qualified sales meetings for Account Executives through outbound prospecting and inbound lead qualification. Responsibilities include cold calling, personalized email and LinkedIn outreach, account research, CRM and pipeline management, territory planning, AI-assisted workflow optimization, and continuous sales coaching. The role requires developing expertise in enterprise Governance, Risk, and Compliance concepts while working hybrid in Chicago from 6:00 AM to 2:00 PM CT.

Leads a regional client service team supporting customers and brokers. Responsibilities include team recruitment, training, coaching, performance management, account servicing, relationship development, issue resolution, and collaboration with Field Operations, Underwriting, Claims, and Risk Control. Supports prospecting, renewals, submissions, quotes, and new business growth while communicating strategic initiatives, market trends, and business results.

Generate and qualify sales opportunities through cold outreach, inbound lead response, discovery calls, and relationship building with trucking carriers. Collaborate with Account Executives on outreach and lead handoffs, develop expertise in Toro’s transportation management software and industry, understand competitors, and consistently achieve qualified-opportunity and sourced-ARR quotas. This is an in-office Chicago role designed for upcoming graduates beginning careers in software sales.

The Sales Development Representative will prospect new accounts, initiate sales cycles, qualify prospects, and build pipeline for Account Executives through cold calling, email, social selling, and AI-powered outreach. Responsibilities include using intent data and sales intelligence tools, crafting personalized messaging, collaborating with Marketing, meeting activity and opportunity targets, and developing expertise in Cleo’s AI-driven integration platform. The role offers SaaS sales training and advancement into future sales positions.

Leads the East region’s Mid-Market and Small Group sales team, coaching sellers, managing pipeline and forecasts, driving quota attainment, and developing talent. The role oversees approximately 10–12 direct reports, supports broker and consultant relationships, attends client and industry events, contributes to sales-model improvements, and partners cross-functionally on hiring, onboarding, performance management, and seller development.

Drive new corporate business by converting prospective clients into customers, generating and managing qualified pipeline, conducting customer research, delivering product demonstrations, and exceeding activity and revenue metrics. Collaborate with BDRs, solution engineers, and sales support teams while developing trusted-advisor relationships and expertise in Sprout Social’s platform and social media trends.

Drive new enterprise business across assigned global accounts by generating pipeline, engaging IT, science, and data stakeholders, forecasting sales, presenting solutions, negotiating complex deals, and closing new business. Build relationships across multiple personas and executive levels, manage account data in Salesforce, collaborate with marketing, product, customer success, and partners, and apply structured sales methodologies such as MEDDICC to achieve revenue targets.

Supports sales of highly technical TIC services by managing account portfolios, identifying opportunities, communicating product value, and serving as a technical liaison between customers, account owners, and delivery teams. Builds customer relationships remotely and through limited travel, supports sales cycles, coordinates technical resources, and works toward exceeding sales targets.