Top Tech Jobs & Startup Jobs in Chicago, IL

Owns the roadmap, strategy, discovery, prototyping, delivery, launch, adoption, and lifecycle management for a B2B SaaS product area. Partners with customers, engineering, design, sales, marketing, and customer success to prioritize work, define requirements and metrics, ship valuable features, evaluate results, and guide product improvements. The role requires strong customer research, technical judgment, data fluency, AI familiarity, and comfort operating independently in ambiguous, highly compliant environments.

Leads strategy, roadmap, and business outcomes for AbsenceSoft’s compliance engine and enterprise platform. Oversees product managers and domain experts, expands regulatory coverage, guides platform capabilities such as identity, configuration, integrations, and data, and partners with Engineering, Legal, Sales, and executives. The role requires enterprise B2B SaaS product leadership, AI governance in accuracy-critical domains, measurable commercial results, and experience scaling complex compliance and platform products.

Leads annual budgeting, quarterly forecasting, long-range planning, financial modeling, and variance analysis. Partners with executives, the CFO, Sales, Marketing, and department leaders to provide insights for strategic decisions. Manages and develops the FP&A team, improves reporting processes and automation, supports accounting close activities, and evaluates business scenarios, investments, and partnerships in a SaaS environment.

Design, develop, deploy, and optimize AI and machine learning solutions for an employee leave management platform. Responsibilities include building scalable models, applying NLP and predictive modeling, implementing MLOps practices, developing secure data pipelines, collaborating with product and engineering teams, and ensuring ethical AI through fairness, transparency, and bias detection.

Leads a team of 4–8 Solutions Consultants supporting sales through demos, discovery, deal strategy, and technical consultation. Responsibilities include hiring, coaching, performance management, process standardization, strategic deal participation, pipeline reviews, customer feedback, and collaboration with Sales and Product leadership. The role improves win rates, onboarding speed, team consistency, and presales performance while maintaining security and compliance controls.

Own a core product area end-to-end: set strategy and roadmap, lead discovery and specs, partner with engineering and design to ship, instrument and track post-launch metrics, translate customer insights into prioritized product work, and present outcomes to executive leadership while maintaining security/compliance.

Own the end-to-end TPA and PEO sales motion within an assigned region, managing existing opportunities and new targets. Conduct prospecting, discovery, presentations, negotiations, contracting, forecasting, and relationship development across deal sizes. Tailor solutions to HR, compliance, and workforce-management needs while partnering with Sales Engineering, Marketing, Legal, Product, and Customer Success. Serve as the internal TPA/PEO market specialist and maintain accurate pipeline visibility.

Leads the design, development, and delivery of complex software systems. Drives architectural decisions and technical strategy, mentors engineers, conducts code reviews, partners with product stakeholders, and improves system performance, scalability, security, and compliance. Owns technical initiatives from design through delivery while maintaining high engineering standards.

Leads and develops a customer success team, drives adoption, retention, customer health, and satisfaction outcomes, and manages complex escalations. Builds scalable CS processes, playbooks, and frameworks; contributes to organizational strategy; analyzes customer data; supports expansion opportunities; and leads cross-functional initiatives with Sales, Product, Support, and Implementation. Represents the company externally and maintains departmental security and compliance controls.

Manage a portfolio of SaaS customers as a trusted advisor, driving onboarding, adoption, retention, expansion, and measurable value realization. Develop success plans, monitor customer health, mitigate churn risks, resolve complex issues, and collaborate with Sales, Product, and Support. Capture customer insights for product and process improvements while maintaining security and compliance standards.