Top Tech Jobs & Startup Jobs in Chicago, IL

Lead vision and strategy for Payments and Risk, owning KPIs like payments GMV, net take, and losses. Manage and grow a team of Product Managers, partner with Engineering, Design, Risk, and Analytics, and drive AI-enabled product solutions and platform services to improve cashflow, risk protections, and payment experiences for B2B/vertical SaaS customers.

Design, develop, and facilitate training across the organization. Collect and analyze effectiveness data, manage scheduling and administration, identify training needs, and collaborate with stakeholders to maintain and evolve curriculum. Lead performance discussions and support Enablement team initiatives to scale training programs.

Consultative sales role owning the conversion funnel for home-service customers: run 3–5 virtual demos daily, qualify and close transactional opportunities, coordinate with SDRs, and support early onboarding to drive long-term product adoption.

Consultative SaaS sales role owning the conversion funnel: run virtual demos, qualify and nurture a high-volume pipeline, close contracts, coordinate with SDRs, and facilitate early onboarding to drive long-term customer success for home service professionals.

Lead and mentor product managers to deliver enterprise B2B SaaS solutions. Define and execute enterprise product strategy, translate complex customer needs into scalable roadmaps, partner with Engineering, Design, Analytics and GTM teams, set KPIs, and manage risk, compliance, and platform stability to drive retention and ARR expansion.

Lead strategy and execution of data-driven paid acquisition across search, social, display, and affiliates. Manage budget allocation, team leadership, experimentation, AI-driven automation, channel launches, cross-functional reporting, and vendor/agency relationships to drive CAC, ROAS, LTV, and revenue growth.

The Senior Director of Customer Success leads the strategy for the department, enhancing the customer journey, retention, and performance standards while collaborating cross-functionally.