Top Tech Jobs & Startup Jobs in Chicago, IL

Lead end-to-end delivery of 2-3 large SaaS customer implementations, triage cross-functional issues, build repeatable tooling and processes, mentor teammates, and feed implementation learnings into Product and Engineering while advancing AI-enabled workflows.

Design end-to-end lending and loan-application experiences for borrowers and credit union operators. Lead discovery, research, prototyping (including AI-driven prototypes), and ship production-ready flows. Simplify complex, regulated workflows, create reusable design systems, collaborate with PMs and engineers, run research and usability testing, and raise design craft across the team.

Own the company’s annual planning, quarterly OKR cycles, operating cadence, and business metrics foundation. Build client margin, cost-to-serve, unit economics, cohort performance, and repeatable analytics. Pressure-test forecasts and business cases, facilitate cross-functional decision-making, define company metrics, and establish reporting processes. As the first dedicated Business Operations hire, independently perform analysis, lead executive-facing meetings, document decisions, and eventually build the function and team.

Manage a 12–15 mid-market enterprise portfolio of Credit Union customers, lead executive onboarding, drive adoption and value realization, run QBRs/EBRs, surface data-driven insights, collaborate with product/implementation/support, and generate qualified expansion opportunities to grow ARR.

Own end-to-end onboarding implementations for credit union customers, driving project plans, status reporting, risk mitigation, and cross-functional accountability. Partner with implementation engineers and executive sponsors, prescribe product-led solutions, build methodology and process, and mentor teammates to scale implementation practices across the organization.

Partner with GTM (Sales, Marketing, Customer Success) to own GTM financial models, forecasts, and reporting. Deliver KPI dashboards, variance analysis, board/QBR packages, and analyses that guide hiring, commission, and spend decisions. Embed with GTM leaders to influence investment and improve forecasting accuracy.

Serve as a strategic HR partner to leaders in a high-growth SaaS company. Build performance, accountability, culture, leadership judgment, and internal communication systems from the ground up. Coach managers through ambiguous and sensitive employee situations, advise on organizational health, and strengthen consistency across the leadership layer. Partner with HR Operations and the HRBP Lead while using AI to improve HR and company-wide efficiency.

Own People Operations workflows and systems, including onboarding, offboarding, employee lifecycle changes, compliance, benefits administration, vendor management, engagement and recognition programs, and performance and compensation cycle logistics. The role improves processes through automation, maintains audit-ready documentation, supports employees, coordinates with IT, Legal, and Finance, and independently launches and communicates company-wide People programs.

Own an enterprise territory selling Clutch’s vertical SaaS platform to credit unions. Responsibilities include managing inbound leads, generating outbound pipeline, conducting demos and technical conversations, shaping RFPs, navigating multi-stakeholder sales cycles, and closing $150K–$300K+ ACV deals against a $1M+ annual quota. The role requires deep credit union industry knowledge, consistent prospecting, strategic selling, and willingness to travel for customer meetings.

Own post-sale delivery and ongoing performance of credit-union-facing AI agents (Emma): design conversation behavior, run live testing and go-lives, monitor quality and drift, run executive business reviews, codify playbooks and monitoring, and build the operating model and team to scale the function.