Top Tech Jobs & Startup Jobs in Chicago, IL

Lead, coach, and develop a team of 8–12 sales representatives. Drive pipeline generation, improve sales processes, monitor performance through data and dashboards, support hiring, and establish scalable workflows. The role is responsible for achieving revenue or pipeline targets, developing sales talent, and building a high-performance sales culture.

Own the full sales cycle for prospective and existing early education customers, including outbound outreach, discovery, product demonstrations, pipeline management, and deal closing. Achieve monthly revenue and unit goals while using Salesforce to track activity and follow-ups. Build customer relationships, understand business needs, position brightwheel’s value, and continuously improve through coaching, call reviews, and feedback.

Lead Expansion Revenue Operations by designing scalable sales processes, lead scoring, routing frameworks, funnel analytics, and AI-driven workflows. Partner with Sales, Finance, Product, and executive stakeholders to improve go-to-market decisions. Present insights to senior leaders, monitor production systems, and hire, coach, and develop a high-performing team.

Own Brightwheel’s demand generation function, including pipeline and revenue targets, budget, team leadership, channel strategy, and performance measurement. Diagnose and modernize the existing function, shift from MQL-based marketing to signal- and intent-based approaches, launch emerging channels, integrate AI and agentic tools into marketing workflows, and partner with Sales on funnel definitions, service levels, and conversion quality.

Leads complex, cross-functional go-to-market initiatives for Education and Curriculum products, spanning opportunity identification, positioning, channel strategy, sales enablement, launch, and performance measurement. Develops growth strategies and business cases using customer, market, and performance data; partners across Sales, Marketing, Finance, and Analytics; establishes metrics and scalable operating processes; and communicates recommendations to executives.

Leads a full-stack engineering team developing customer-facing SaaS products across web, mobile, backend, and AI systems. Owns engineering strategy, architecture, reliability, security, privacy, delivery planning, product health, and measurable customer outcomes. Partners with Product, Design, and customer-facing teams to define and ship products, uses production data to guide priorities, and hires, develops, and manages engineering talent.

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.

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 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.