Top Tech Jobs & Startup Jobs in Chicago, IL

Lead AI Edge content strategy and production across blog posts, newsletters, video, and creator partnerships. Produce bi-weekly newsletters, repurpose workshop recordings, coordinate creators, collaborate with SEO and paid teams, and ensure evergreen educational content that positions the brand as an authority in AI and tech.

Lead AI Edge content strategy and production across long-form articles, evergreen video, bi‑weekly newsletters, and repurposed workshop/podcast assets. Coordinate creators, partner with SEO and paid teams, and ensure all content educates, builds brand authority in tech/AI, and drives newsletter sign-ups and social engagement.

Originates and closes strategic CPG partnerships to deliver brand-funded offers, discounts, cashback, and shopper marketing programs. Builds executive relationships, negotiates seven-figure deals, drives a multi-year pipeline, represents Sezzle at industry events, and collaborates cross-functionally on product, data, marketing, legal, and finance to measure ROI and scale repeatable playbooks.

Lead developer experience strategy and build platform tooling to improve productivity, CI/CD, testing, deployment automation, and reliability. Design golden paths, reduce tooling fragmentation, collaborate across teams, and iterate on AI-assisted tooling and evaluation to enable hundreds of engineers to build, test, and ship with speed and confidence.

Lead and execute a large, cross-functional transformation (Connected Tax Platform Experience) by translating strategy into execution plans, managing dependencies, risks, governance, and release readiness. Align Product, Engineering, Architecture, UX, Data, and Operations; provide executive reporting and decision frameworks; leverage AI-assisted workflows and automation to improve delivery velocity, readiness, and customer outcomes. Coach TPM practices and drive scalable operating models for enterprise platform delivery.

Lead end-to-end proposal development for federal, state, and local government opportunities. Manage solicitation analysis, compliance matrices, schedules, writing and editing non-technical sections, coordinating reviews and production, maintaining proposal libraries, and supporting opportunity qualification and process improvements to win mission-driven work.

Identify and qualify new sales opportunities through high-volume outbound prospecting and inbound lead management. Use Salesforce, SalesLoft, and LinkedIn Sales Navigator to research, prioritize, and engage prospects, meet weekly/monthly metrics, and align with Account Executives to build pipeline.

Build and run an end-to-end CRO operating system: prioritize and manage an always-on testing backlog, own the full test lifecycle, translate wins into scaled implementations, integrate test insights with paid media and creative, optimize conversion rate and contribution margin across funnels, design offer and funnel architecture, and lead CRO reporting and collaboration across Growth, Design, and Analytics.

Operate and scale the identity platform and access governance program: lifecycle provisioning/deprovisioning, B2B guest governance, non-human identity management, SSO/SCIM integrations, privileged access controls, IAM audit support, endpoint/MDM and SaaS administration, and escalated end-user support. Partner with MSP and cyber team to secure identities and respond to identity-related incidents.

Support and secure multi-cloud (AWS, Azure, GCP, OCI) IL2-IL6 environments: design, deploy, and maintain authorizations/ATO/IATT via RMF and eMASS; implement cATO and automation; run vulnerability/compliance scanning and STIG remediation; produce reports and briefings; mentor staff and perform cyber management duties.