Top Tech Jobs & Startup Jobs in Chicago, IL

Partners with corporate leaders on performance, employee relations, compensation, career development, workforce planning, and manager coaching. Leads calibration, promotion, and merit cycles; advises on complex employee matters; designs scalable HR processes; owns strategic people initiatives; applies AI to improve HR workflows; and mentors fellow HR partners.

Build and scale the sales engine for Brightwheel’s education products. Responsibilities include developing go-to-market strategy, prospecting, managing the full sales cycle, creating pipeline, closing early customers, understanding education buyers, and translating market feedback into product, positioning, processes, and repeatable sales playbooks.

Lead cross-functional go-to-market programs to scale multi-product selling, redesign Salesforce workflows, deploy AI-driven automations, align stakeholders, build KPI-driven analyses, and drive adoption and efficiency across Sales, Marketing, Finance, and Systems Operations.

Own end-to-end AI-powered product improvements: design and build cross-cutting AI services (retrieval, evaluation, guardrails), define success metrics, prototype to production, create shared AI tooling and abstractions, shape data and system architecture for safe longitudinal signals, mentor engineers, and ship reliable, secure production systems that improve educator and family outcomes.

Lead and execute full-stack SEO, AEO, and GEO strategy to drive high-intent traffic and MQLs. Manage large-scale AI-assisted content production, implement technical schema and llms.txt, track AI citation visibility, conduct audits, and align cross-functional teams to connect SEO work to pipeline and revenue.

The Director of Training & Enablement will manage a unified team, define an AI-first enablement strategy, and improve onboarding and performance metrics.

Own the full sales cycle for existing brightwheel customers, from outbound prospecting and discovery through product demos and deal closure. Conduct high-volume outreach in Spanish and English, expand customer product adoption, achieve monthly revenue and unit goals, maintain accurate Salesforce pipeline data, and position products against competitors. The role requires consultative selling, strong organization, resilience, adaptability, and fluent bilingual communication.

Designs, builds, and operates AI-powered solutions for go-to-market teams, including retrieval, context, evaluation, guardrails, agent workflows, and operational automation. Owns problems end to end from discovery through launch, measurement, and iteration while shaping data and system architecture. Establishes reusable AI tooling, improves engineering velocity through AI-augmented development, mentors engineers, and maintains high standards for reliability, privacy, security, observability, and customer trust.

Lead and build new ventures end-to-end at brightwheel: discover customer needs, prototype and ship AI-enabled products, prove business models and unit economics, recruit and grow teams, and drive outcomes with the CEO and executive team toward product-market fit and scale.

Lead and own the technical systems and teams that run operations, redesign GTM architecture for AI, manage managers and ICs, drive company-wide AI-native capabilities, and personally deliver high-priority technical initiatives that improve business outcomes.