Top Tech Jobs & Startup Jobs in Chicago, IL

Owns B2C growth and the full customer lifecycle for a professional education business, from acquisition and enrollment through course completion, exam readiness, licensure, and continuing education. Leads revenue, contribution, customer acquisition efficiency, conversion, retention, and learner outcomes. Directs cross-functional Marketing, Product, Sales, and Operations priorities while standardizing growth strategies across brands and markets. Uses data, AI, automation, and personalization to improve customer and business performance.

Supports drafting, reviewing, redlining, negotiating, and managing commercial customer and vendor agreements. Reviews legal and business risks, participates in negotiations, conducts contract-related research, and advises business stakeholders. Maintains contract lifecycle documentation, approvals, records, and status tracking while using contract management systems and AI-enabled legal technology. Escalates higher-risk matters, communicates with senior counsel, and helps improve templates, processes, and contracting efficiency.

Develops and updates CPA and EA tax-focused curriculum, including textbooks, lectures, questions, flashcards, and related learning materials. Reviews SME content, maintains mappings to technical guidance, trains subject matter experts, and guides production teams. Manages content development timelines, supports custom curriculum projects, monitors accounting profession trends, collaborates cross-functionally, and applies instructional design principles to explain technical accounting concepts.

Drafts, reviews, and negotiates customer- and vendor-side commercial agreements, including SaaS, technology, licensing, privacy, and services contracts. Improves contracting operations through templates, playbooks, approval processes, lifecycle management, automation, reporting, and contract technology adoption. Supervises and develops contract specialists while partnering with Sales, Finance, Procurement, Privacy, Security, Technology, Product, Marketing, and other teams.

Leads and coaches a nationally distributed B2C sales team of 12–20 professionals. Responsibilities include conducting one-on-ones and call coaching, improving conversion and productivity, tracking sales performance, removing operational and system roadblocks, reinforcing CRM discipline, and partnering cross-functionally on hiring, onboarding, workforce planning, reporting, and process improvements.