Top Tech Jobs & Startup Jobs in Chicago, IL

Own and continuously improve the Account Executive onboarding program from curriculum development through delivery and measurement. Manage training content, playbooks, tools, communications, and learning systems while supporting ongoing enablement programs. Partner cross-functionally with Sales, Marketing, Product, RevOps, and IT to maintain relevant training, coordinate access, troubleshoot systems, and connect learning outcomes to business goals.

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.

Manage and grow a high-volume portfolio of business customers by expanding revenue, reducing churn and downsell risk, and increasing product adoption. Responsibilities include partnering with Account Directors, analyzing Salesforce and usage data, conducting QBRs, engaging senior stakeholders, delivering product training and webinars, answering technical questions, and meeting activity and retention targets.

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 implementation strategy and integration workstreams for Engine X corporate card customers. Owns deployments from contract through first transaction and adoption, including ERP, HRIS, SSO, and expense-platform integrations. Partners with Sales, Product, and Engineering to resolve implementation blockers, shape product priorities, scope complex deals, define technical requirements, and accelerate time to first transaction. Also provides senior leadership for corporate card program implementations.

Lead and scale business and GTM recruiting across multiple corporate functions. Develop talent acquisition strategies, workforce plans, hiring metrics, recruiting processes, employer brand initiatives, and candidate experience improvements. Build and mentor a high-performing recruiting team, advise senior leaders, and integrate AI and automation into sourcing, screening, assessment, scheduling, and pipeline management.