Top Tech Jobs & Startup Jobs in Chicago, IL

Lead product design strategy and execution for complex HighLevel platform experiences. Partner with product, engineering, research, and data teams to define vision, design workflows, improve usability and accessibility, and establish scalable design standards. Use customer insights and metrics to guide decisions, lead quality reviews, mentor designers, facilitate critique, and influence product direction across a distributed remote organization.

Leads the Data Platform and Infrastructure team, owning strategy, architecture, execution, and organizational development. Responsibilities include managing and mentoring engineers, guiding data ingestion and platform design, establishing APIs, SLAs, governance, security, monitoring, disaster recovery, and cost optimization. The role partners with Product, Data, Finance, Security, and Analytics teams to enable reporting, experimentation, machine learning, and data products while scaling reliable infrastructure and developing future technical leaders.

Build and own enablement infrastructure for HighLevel’s affiliate organization. Responsibilities include onboarding affiliate managers and new affiliates, creating learning paths, playbooks, SOPs, call frameworks, coaching programs, product knowledge standards, and lifecycle communications. Analyze performance data, optimize affiliate activation processes, provide stakeholder reporting, and represent HighLevel at affiliate events while building partner relationships.

Lead HighLevel’s Customer Escalations function, managing and developing a team handling complex customer issues. Personally resolve sensitive escalations, coordinate cross-functional solutions, establish scalable processes, and identify recurring friction. Use customer insights, data, automation, and operational improvements to enhance customer outcomes, prevent repeat issues, and improve the broader customer journey across Support, Success, Product, Engineering, Billing, and RevOps.

Leads company-wide pricing, packaging, monetization, customer research, experimentation, and commercial strategy for a B2B SaaS platform. Develops pricing architecture, customer segmentation, financial models, competitive intelligence, and monetization roadmaps. Partners cross-functionally to implement and measure pricing initiatives, improve conversion, expansion, retention, gross margin, and customer lifetime value, while building the organization’s pricing and customer insights capabilities.

Develops new business opportunities with sponsors, exhibitors, and marketplace companies. Responsibilities include prospect research, targeted outreach, relationship building, networking at industry events, sponsorship and exhibitor sales, pipeline management, CRM updates, and opportunity development. The role independently manages assigned opportunities, collaborates with sales and internal teams, and progressively assumes ownership of strategic opportunities and the full sales cycle.

Lead complex product design initiatives across multiple teams and workflows. Define experience direction, create prototypes and high-fidelity designs, shape AI-enabled interfaces, strengthen design systems and accessibility, and mentor designers. Partner with product, engineering, research, data, and customer-facing teams to translate customer needs and business goals into coherent, high-quality shipped experiences in a remote environment.

Lead and develop a distributed team of 8–12 product designers delivering AI-powered workflows across product and revenue experiences. Set quality standards, guide design strategy, lead critiques and coaching, partner cross-functionally on roadmaps and tradeoffs, and ensure usability, accessibility, consistency, and launch readiness. Hire and develop talent while staying close to design decisions and using AI-assisted tools to improve exploration, prototyping, synthesis, documentation, and collaboration.

Lead Revenue Operations for Implementation and Customer Success, building forecasting, KPI, retention analytics, health scoring, workflow, and reporting frameworks. Partner with senior leaders on planning, business reviews, investment cases, tooling, and process design. Connect implementation and CS activities to churn, retention, customer lifetime value, and expansion revenue. Govern Freshdesk operations, Success AI performance, data integrity, and cross-functional improvements while developing analysts and influencing executives.

Own revenue operations for the Affiliates organization, including GTM planning, forecasting, analytics, process design, affiliate program tracking, payout coordination, ROI measurement, and tech-stack management. Partner with leadership through business reviews and recommendations, automate operational workflows, and manage and develop a small analyst team in a high-growth SaaS environment.