Top Tech Jobs & Startup Jobs in Chicago, IL

Owns end-to-end enterprise sales across major K-12 school districts, including territory strategy, pipeline development, consultative selling, executive relationship building, complex procurement, and long sales cycles. Partners with Product, Marketing, Success, Implementation, and Legal teams to drive adoption and expansion. Represents ClassDojo through district visits, conferences, and strategic meetings while consistently achieving sales targets.

Owns end-to-end onboarding and implementation for up to 20 enterprise K-12 districts. The role manages project timelines, professional development, communications, adoption strategies, stakeholder alignment, technical readiness, and data-informed interventions. It coordinates district IT teams with internal Product, Engineering, Data, and Technical Implementation teams, supports SSO and roster integrations, and translates enterprise needs into prioritized work. The position also improves onboarding processes and serves as an executive-level partner to district leaders.

Own external user acquisition for ClassDojo’s consumer products by developing strategy, running end-to-end growth experiments, testing paid and unpaid channels, and scaling successful programs. The role focuses on social and influencer partnerships, ROI measurement, conversion optimization, experimentation frameworks, and cross-functional collaboration with Product, Creative, Data, and Marketing. It is a highly autonomous individual-contributor role with potential future people leadership.

Lead all legal functions, including product, privacy, commercial, corporate, employment, intellectual property, regulatory, and litigation matters. Advise founders and leadership, shape policy for children’s technology and AI, manage regulators and outside counsel, accelerate contracting, build legal playbooks, lead a small in-house team, apply AI to legal workflows, and oversee M&A, financings, and board matters.

Lead and scale ClassDojo’s accounting and tax operations, including monthly close, audits, financial reporting, controls, GL, AP, revenue accounting, payroll, equity, tax, and treasury. Build financial systems, processes, and teams; ensure US GAAP compliance; partner with executives and cross-functional leaders; and support strategic initiatives including M&A, fundraising, secondary transactions, and a potential IPO.

Conduct full-cycle recruiting across technical and non-technical roles, including sourcing, candidate outreach, recruiter screens, interview coordination, hiring-manager partnership, pipeline management, and candidate experience. Maintain accurate ATS data and support recruiting projects and process improvements in a fast-moving, distributed technology company.

Own the company-wide IT function for approximately 350 employees, including identity, device management, SaaS administration, onboarding and offboarding, support, security operations, vendor and budget management, AI platform governance, automation, and SOC 2 controls. Maintain Okta, Google Workspace, Slack, Mac MDM, passwordless authentication, HRIS-driven lifecycle automation, and self-service IT systems while improving efficiency and documentation.

Design and build internal platforms, tooling, and AI-powered workflows to reduce developer friction, improve velocity, quality, and reliability. Partner with product, infra, and security to create reusable paved paths, measure impact with engineering metrics, and help define the Developer Experience practice.

Lead a multi-team platform org owning infrastructure, data, developer experience, and AI tooling. Manage managers, set platform roadmap and architecture trade-offs, drive adoption of paved roads/golden paths, ensure SLAs/SLOs and incident readiness, and partner cross-functionally to balance reliability, tech debt, and developer productivity.

The Product Leader will create and scale consumer products for ClassDojo's network, collaborating with teams to innovate and test ideas, aiming to enhance the education experience for children globally. They will use data and user feedback to guide product development and ensure alignment with brand goals.