Top Tech Jobs & Startup Jobs in Chicago, IL

Leads the strategy and outcomes for the SMB customer segment, owning adoption, retention, expansion, and scalable customer success programs. Oversees digital-first engagement across onboarding, adoption, renewal, and expansion; builds and develops the SMB customer success team; establishes coverage models, capacity planning, and efficiency targets; and partners with Sales, Marketing, Product, Education, and Operations to improve customer outcomes using data, automation, and usage signals.

Leads the Customer Success practice for Attendance Plus, managing strategic K-12 accounts while hiring and coaching a CSM team. Builds customer success processes, playbooks, engagement models, and success plans from the ground up. Owns adoption, attendance outcomes, renewals, retention, expansion, and at-risk account intervention. Partners with Sales, Product, Education, and Support, represents customer needs internally, and establishes reporting and HubSpot processes.

Lead strategic finance initiatives, corporate development, M&A evaluation, pricing strategy, business cases, and cross-functional financial analysis. Partner with executives and teams across Product, Sales, Marketing, Customer Success, and Operations to evaluate growth opportunities, ROI, unit economics, and build-versus-buy decisions. Develop KPI reporting frameworks, AI-enabled analysis, automated workflows, and executive recommendations.

Own the full lifecycle of 70+ annual trade shows, conferences, and virtual events, including research, registration, logistics, budgets, materials, travel, and vendor coordination. Drive pre- and post-event lead generation, track leads in the CRM, and measure event ROI. Coordinate associations, executive speaking opportunities, branded swag, inventory, and cross-functional collaboration with Sales, Customer Success, and leadership. Travel to at least two key events annually.

The Staff Engineer will lead cross-functional teams, focus on AI development practices, ensure scalable engineering, and evolve system architecture at ParentSquare.

Own the market strategy, positioning, messaging, pricing, packaging, segmentation, and go-to-market plans for Attendance Plus. Research chronic absenteeism, district buying dynamics, competitors, and customer needs to guide product and business decisions. Lead launches, measure adoption, conduct win-loss analysis, enable Sales and Customer Success with messaging and competitive tools, and align cross-functional stakeholders. Travel to industry events and conferences approximately 20% of the time.

Build and lead complex data integration projects from client onboarding through ongoing platform usage. Analyze and resolve data discrepancies, troubleshoot SIS and SSO integrations, develop internal Retool applications, perform code reviews, prioritize backlogs, manage projects, and mentor teammates. The role requires advanced SQL, development expertise, technical leadership, and collaboration with internal stakeholders, with Ruby on Rails, AWS, Git, and K-12 education experience preferred or desired.

Conduct outbound and inbound outreach to qualify leads, manage a territory and pipeline, deliver online product presentations, document activity in HubSpot, and consistently meet quota while providing excellent service to prospects.

Own a regional territory to drive ARR by developing relationships with K-12 districts, conducting in-person meetings and conferences, managing pipeline in HubSpot, responding to RFPs, delivering demos, closing contracts, and coordinating handoffs to Customer Success.

Sell and close ParentSquare solutions to SMB K-12 customers by building territory plans, managing a HubSpot pipeline, conducting demos, responding to RFPs, collaborating with Customer Success for handoffs, and meeting/exceeding ARR quotas through consultative selling and upsell/cross-sell efforts.