Top Tech Jobs & Startup Jobs in Chicago, IL

Build and optimize HubSpot environments across multiple clients, including CRM architecture, data governance, workflows, automations, integrations, APIs, webhooks, migrations, reporting data, and troubleshooting. Audit data quality, resolve integrity issues, establish scalable standards, document systems, and improve CRM reliability and performance within an agency or client-services environment.

Designs and scopes RevOps solutions for prospective clients by auditing HubSpot and sales infrastructure, identifying operational gaps, and translating business needs into solution architectures, implementation plans, SOWs, deliverables, and pricing. Partners with sales and delivery teams to validate technical feasibility, support technical sales conversations, communicate recommendations, and ensure smooth handoff into implementation.

Configure, optimize, and maintain HubSpot CRM environments supporting sales and revenue operations. Responsibilities include workflow and pipeline configuration, data integrity and governance, CRM audits, automation, client account deployments, integrations with sales technology, reporting support, documentation, enablement, and troubleshooting. The role partners with RevOps, sales leadership, data teams, and clients to improve scalability, system reliability, sales productivity, and revenue visibility.

Remote independent-contractor closer selling high-ticket coaching and consulting to founders and executives. Conduct consultative conversations about revenue, KPIs, team structure, and strategic priorities; diagnose business challenges, communicate ROI, build trust, and consistently close deals to meet revenue goals.

Conduct 25–30 inbound Zoom consultations weekly with high-net-worth retirees, using a consultative framework to assess retirement tax exposure, educate on advanced strategies, create decision-driving moments, manage pipeline and CRM, and close sales while a planning team handles implementation.

Conduct consultative discovery calls with motivated real-estate investing prospects, uncover goals and financial motivations, build trust and certainty, present program fit, convert qualified appointments into enrolled clients, and exceed revenue goals while delivering an exceptional prospect experience.

Lead remote high-performance sales teams for outsourced, lead-generation clients in alternative education. Own pipeline management, forecasts, CRM accuracy, rep performance, training, call reviews, process improvements, hiring/onboarding, and revenue outcomes to maximize sales and ROI.

Lead and manage remote high-ticket sales teams for alternative education clients. Oversee pipeline management, call reviews, CRM/reporting accuracy, quotas and projections, onboarding and training, collaborate with marketing, identify process and enablement improvements, and take full revenue ownership for assigned accounts.

Remote independent-contractor role selling high-ticket consumer services. Perform consultative sales calls: discover customer needs, build credibility and trust, diagnose problems, educate prospects, and guide them to purchase. Consistently exceed revenue targets and create a professional buying experience without pressure tactics.

Lead and own the full learning lifecycle for sales hires: design onboarding and role-specific curricula, run training cohorts and enablement, review calls at scale, build performance-based coaching frameworks tied to revenue, partner with Sales Directors, maintain playbooks and SOPs, and continuously optimize training to shorten ramp time and improve conversion and productivity.