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.

Owns post-onboarding sales enablement for the outbound organization, including training, playbook development, rep certification, performance evaluation, tool adoption, and continuous improvement. Partners with sales leadership, revenue operations, marketing, product, partnerships, and frontline managers to improve sales effectiveness and revenue outcomes. Uses Salesforce, Outreach, call coaching, and project management tools to benchmark performance and deliver enablement programs in a fast-growth SaaS environment.

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.

Drive expansion across strategic B2B customer accounts by identifying whitespace, building commercial cases, engaging executive stakeholders, and closing complex multi-stakeholder deals. The role owns opportunities from discovery through pricing, procurement, and close; maintains pipeline accuracy and forecasting rigor; and partners with Account Managers and cross-functional teams. Requires quota-carrying sales experience, strategic or enterprise selling expertise, strong executive presence, 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.

Build and grow strategic hotel partnerships through outbound prospecting, cold calling, relationship development, and consultative sales. Secure direct hotel partnerships, discounted rates, and participation in Engine’s hotel platform and products. Manage named accounts, maintain a clean Salesforce and Outreach pipeline, advise hotel partners on performance tools, and collaborate with relationship management, product, and account management teams.

Leads strategy and operations for the global expansion organization, partnering with revenue leadership on segmentation, account scoring, capacity planning, quotas, metrics, forecasting, and operating cadence. Standardizes post-sale expansion motions, develops AI and automation strategy, and partners with systems and enablement teams to improve productivity. Builds analytical models and insights for leadership while hiring and managing a team of analysts and operations partners.

Lead partnership acquisition strategy for Engine’s transportation and trucking vertical. Identify, negotiate, and close enterprise partnerships across fleet payments, TMS, telematics, ELD, fuel networks, and industry associations. Build executive relationships, onboard partners, coordinate integrations and go-to-market launches, and track pipeline, signed partnerships, and revenue KPIs. The role requires enterprise sales or business development expertise, financial acumen, scalable partner-led sales experience, and familiarity with transportation, logistics, or fleet ecosystems.

Own sales operations strategy and execution, including process design, forecasting, performance reporting, account assignments, compensation plans, Salesforce data quality, dashboards, and cross-functional business initiatives. Partner with sales leadership, finance, data, and product teams to improve workflows, support planning, identify risks and opportunities, and drive operational effectiveness.