Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Owns an AI agent from customer discovery through production launch and roadmap development for credit unions. Responsibilities include rapid prototyping, customer and executive engagement, enterprise implementations, reusable integrations with core banking, loan origination, and CRM systems, product go-lives, launch sequencing, and transition to scaled operations. The role requires strong product judgment, B2B enterprise experience, hands-on AI work, customer presence, persuasive communication, and approximately 20% travel.

Own the account-opening acquisition and onboarding roadmap, improving funnel conversion, attribution, and campaign performance for credit union partners. Analyze application drop-off, define metrics, prioritize initiatives, run experiments, and deliver roadmap outcomes through multiple engineering squads. The role requires cross-functional influence, partner engagement, build-buy-partner evaluations, and clear communication with senior leadership. This is a remote position with company off-sites approximately twice per year.

Drive net-new business with large credit unions by owning complex B2B SaaS sales cycles from prospecting through close. Build territory plans, conduct discovery and demos, develop ROI-based business cases, navigate executive buying committees, manage strategic partners, maintain a 3x-plus pipeline, forecast accurately, close six- and seven-figure deals, and advise executives on digital transformation. Travel 35–45% for prospect meetings, events, and partner activities.

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.

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 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.

Lead technical sales efforts by designing solutions, configuring demos for consumer lending and deposits, running full sales cycles, owning technical discovery, introducing AI-enabled workflows, and acting as the default escalation for integration-heavy and compliance-sensitive deals.