Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and build Fleetio's product marketing and GTM commercialization function. Create repeatable launch frameworks, positioning, messaging, pricing, sales plays, and enablement. Align Product, Sales, Marketing, Customer Success, and Partners; hire and grow a commercialization team; establish operating rhythms, templates, and metrics to drive adoption, pipeline, and revenue.

Drive new business for Fleetio by prospecting and closing mid-market customers. Conduct consultative sales, perform web-based demos, manage inbound and outbound pipeline, negotiate pricing, and collaborate cross-functionally to grow ARR. Role requires consistent follow-up and up to 20% travel.

Lead lifecycle marketing to move users from interest through activation, conversion, adoption, expansion, and retention. Design segmented, data-driven email and automation programs for PLG, mid-market, and enterprise motions. Partner cross-functionally to build scalable nurture, onboarding, and usage-based campaigns, measure lifecycle metrics, run experiments, and optimize funnel conversion and revenue outcomes.

Sell Fleetio SaaS to small and medium businesses via inbound and outbound outreach. Conduct consultative web demos, qualify prospects, generate pipeline, negotiate pricing, and close deals while driving ARR growth and collaborating with cross-functional teams.

Manage outbound lead generation for Mid-Market: research and contact prospects via calls, email, and social; build CRM lead profiles; qualify accounts; schedule meetings and demos; support Account Executives and strategic efforts to create qualified sales opportunities.

Lead and scale a global accounting organization for a high-growth SaaS and payments company. Oversee monthly close, financial reporting, consolidations, audits, controls, tax, billing, collections, payroll and finance operations. Improve processes, automation, and cross-functional partnerships while building a high-performing team to support global, multi-entity operations and future strategic transactions.