Top Tech Jobs & Startup Jobs in Chicago, IL

Own the full B2B customer journey from onboarding through adoption, retention, renewals, and expansion. Improve time-to-value, gather structured feedback for product and engineering, support contract processes, and build customer success playbooks and metrics. Partner with founders on go-to-market experiments, product-market fit, and growth initiatives while developing strong customer relationships.

The Founding Sales Development Representative will build Reflow’s outbound prospecting engine from scratch. Responsibilities include prospecting named enterprise accounts, conducting multi-channel outreach, booking qualified meetings, testing segments and messaging, documenting the sales playbook, tracking activity and outcomes, and sharing market feedback. The role requires resilience, strong writing, systems thinking, coachability, and interest in operations and workflow challenges, with potential growth into an AE or SDR leadership role.

In this role, you will define and execute the go-to-market strategy, drive growth, and lead customer success efforts at Reflow, a workplace intelligence platform.

Own full-cycle recruiting for technical roles, source senior talent in Europe and Latin America, and enhance candidate experience while improving recruiting processes.

Develop and optimize AI pipelines for workflow intelligence, experiment with models, and collaborate to integrate AI systems into workflows.

As the Fractional Finance & Strategy Lead, you'll model finances, analyze unit economics, build pricing models, and prepare investor materials.

As a Product Manager at Reflow, you will lead product strategy, execution, and delivery while ensuring customer engagement and managing engineering dependencies in an early-stage startup environment.

The Account Executive will own the full sales cycle, from discovery and demos to closing deals with mid-market and enterprise customers. Responsibilities include qualifying accounts, maintaining accurate forecasts, and collaborating with product teams, while aiming for growth and refining sales messaging based on insights from prospects and clients.

Lead the development of the macOS app for Reflow, ensuring performance, integration, and mentoring team members while maintaining quality standards.

Source, enrich, and QA high-quality lead lists from hypotheses using tools like Clay and Apollo. Validate contacts, document methodology, refine lists from sales feedback, and suggest hypothesis improvements to improve GTM experiments.