Top Sales Jobs in Chicago, IL

Generate and qualify sales opportunities through high-volume cold calling, LinkedIn and email prospecting, lead research, targeted outreach, pipeline development, and follow-up. Maintain accurate CRM records, collaborate with account executives, sales managers, and marketing, stay current on product and industry knowledge, and meet performance KPIs. The role offers an advancement path to account executive for high performers.

Lead and develop a team of Account Executives through hands-on coaching, performance management, data-driven sales strategy, and accountability. Set goals, analyze KPIs, address performance issues, remove operational roadblocks, and collaborate with sales leadership, marketing, product, and operations to improve productivity, lead quality, customer satisfaction, and quota attainment.

Leads and develops an SDR team through coaching, performance management, outbound sales strategy, recruiting, onboarding, and career progression. The role sets goals, tracks sales KPIs, improves prospecting effectiveness, promotes SDRs into Account Executive roles, and builds a motivated, inclusive team culture. Requires hands-on leadership of cold calling, objection handling, social selling, outreach cadences, and data-driven performance optimization.

Drive expansion revenue across strategic customer accounts by identifying whitespace, building commercial cases, engaging executive stakeholders, and closing complex multi-stakeholder deals. Responsibilities include strategic discovery, executive selling, account planning, pipeline management, forecasting, and partnership with Account Managers. The role requires quota-carrying B2B sales experience, enterprise selling skills, consistent quota achievement, and regular customer travel.

Leads a team of quota-carrying Account Directors responsible for customer expansion revenue. The role owns quota attainment, forecasting, pipeline discipline, territory strategy, hiring, coaching, executive engagement, and complex deal execution. The leader serves as executive sponsor for strategic opportunities, develops frontline sales talent, partners cross-functionally on account strategy, and uses data to improve win rates, deal size, and pipeline conversion.

Manage the full sales cycle for mid-market accounts, including outbound prospecting, lead qualification, demos, negotiations, and closing. Build and manage named-account pipelines through high-volume cold calling and self-sourced opportunities. Collaborate with Account Management during onboarding, develop customer relationships, and promote Engine’s travel platform. Maintain accurate pipeline data using Salesforce, ZoomInfo, Outreach, and related sales tools while consistently pursuing sales targets.

Leads and develops a partner growth team responsible for GBV, pipeline, activation, retention, expansion, and churn targets. Owns strategic partner relationships, forecasting, Salesforce discipline, account growth plans, cross-functional execution, and talent development. Drives partner performance across Engine’s travel and spend ecosystem while improving handoffs, re-engagement, and operational rigor.

Own and grow an enterprise advertising account portfolio across hotel chains, property management groups, and destination marketing organizations. Drive renewals, upsells, cross-sells, and new-logo sales; develop ROAS-focused media proposals; coordinate campaign launches with Product and Engineering; monitor performance and optimize campaigns; lead QBRs; maintain Salesforce pipeline accuracy; and represent Engine in partner meetings and industry events.

Leads and scales Engine’s channel partnerships team, owning partner-sourced growth from prospecting through signing, activation, and handoff. Builds vertical-specific partnership playbooks, manages pipeline discipline and forecasting, negotiates referral, co-sell, and co-marketing agreements, and personally closes complex enterprise deals. The role hires and develops channel talent, drives cross-functional execution with Sales, Marketing, Finance, and Legal, and ensures partnerships generate measurable revenue.

Own sales strategy and operations for the Groups business, including segmentation, territory design, capacity planning, forecasting, sales process, operating cadence, and executive reporting. Lead AI and automation adoption across the sales motion, partner with finance, systems, enablement, and data teams, and translate analysis into business decisions. Hire and manage a team of analysts and strategy partners while serving as the primary strategic partner to the VP of Sales.