Top Tech Jobs & Startup Jobs in Chicago, IL

Serve as a technical partner to enterprise financial services customers, driving platform adoption, configuration, optimization, and measurable business outcomes. Conduct usage reviews, platform audits, strategic engagements, and executive business reviews while documenting requirements, actions, and ROI. Collaborate with Customer Success, Product, and Engineering teams; advocate for customer needs; share best practices; and improve delivery frameworks. Occasional travel may be required.

Build and operate governed, production-grade AI and LLM systems across Velsera’s products and business functions. The role covers multi-cloud model serving, MLOps and LLMOps, evaluation, governance, security, auditability, RAG, agentic workflows, and enterprise integrations. This senior individual contributor will establish reusable AI platform patterns, deliver customer-facing and internal capabilities, support regulated environments, and guide build-versus-buy decisions while collaborating with engineering, product, security, compliance, scientific, and commercial teams.

Lead technical presales activities for connected-fleet and telematics solutions. Conduct discovery, shape solution approaches, deliver tailored demonstrations, respond to RFPs and technical questionnaires, document requirements, support pilots and evaluations, resolve technical objections, and collaborate with Product, Engineering, Quality, Implementation, and Customer Success. Translate SaaS, hardware, firmware, sensor, connectivity, and data capabilities into customer business value while supporting enterprise, fleet, OEM, and leasing customers.

Provides client service and retirement-plan administration for owner-only 401(k) plans. Responsibilities include answering sponsor and advisor questions, managing plan tasks and communications, supporting compliance projects, coordinating plan setup and termination activities, processing distributions and amendments, completing required tax returns, documenting client work, and handling inbound and outbound calls.

Provides strategic advising and product expertise for Navigate360 Enrollment Success partners. Drives technology adoption, analyzes utilization and partner health data, manages escalations, develops success plans and scalable enablement resources, and collaborates with Product, Engineering, Support, and Partner Success teams. Leads partner meetings, trainings, process improvements, and post-launch interventions to improve enrollment outcomes and partner value.

Own talent sourcing and casting for paid ads, organic social, and TikTok Shop. Source and test 60–80 candidates monthly, maintain a tagged talent roster, coordinate communications and testing, monitor ad performance, proactively recommend talent, and support negotiations with actors and agents. The role requires strategic direct-response casting judgment, strong organization, platform resourcefulness, relationship management, and independent execution in a 20-hour-per-week contract role.

Leads Chomps’ social strategy, platform-native content, community engagement, cultural participation, and paid amplification. Owns social performance through analytics, testing, listening, and emerging AI tools. Manages a community manager and freelance creators while partnering with Creative, Brand, PR, Influencer, Ecommerce, Customer Experience, and Analytics teams. Develops community-management standards, converts audience insights into marketing recommendations, and supports launches, campaigns, retail moments, and marquee brand activations.

Leads global renewals strategy, forecasting, pricing, negotiations, and execution for a recurring-revenue B2B SaaS business. Builds and manages a global renewals team, establishes processes and playbooks, oversees Salesforce workflows and reporting, and owns renewal, churn, contraction, and GRR targets. Partners with Sales, Customer Success, Finance, Legal, Deal Desk, and Revenue Operations to mitigate risk, close renewals, and identify expansion opportunities. Travel may be required up to 20%.

Manage and expand enterprise customer accounts through opportunity creation, territory planning, complex sales-cycle management, renewals, expansions, forecasting, and quota attainment. Build relationships with technical and executive stakeholders at Fortune 500 companies, maintain sales data in HubSpot, develop territory strategy with sales leadership, and partner with Customer Success to drive adoption and growth.

Develops and manages integrated master schedules, cost estimates, budgets, and program performance across aerospace and defense programs. Analyzes risks, dependencies, expenditures, and what-if scenarios; prepares executive and customer reports; recommends corrective actions; and supports consistent cost and scheduling processes across engineering, manufacturing, integration, testing, and launch activities.