Jobs at ParentSquare, Inc

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.

Leads customer support operations by mentoring agents, handling escalations and tier-two tickets, monitoring queues, providing backup coverage, and conducting live coaching. Partners with the Customer Support Manager on training, performance feedback, process improvements, and strategic support initiatives. Requires strong communication, prioritization, SaaS support experience, and prior lead or management experience.

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.

Own a portfolio of large/enterprise Texas K-12 accounts to drive adoption, retention, renewals and expansion. Build success plans, support launches and integrations, deliver training/demos, surface customer feedback, resolve escalations, and collaborate cross-functionally. Travel for conferences and quarterly community events.

Own the end-to-end onboarding, configuration, adoption, retention, and expansion of ParentSquare Pay accounts for school districts. Configure payment and financial settings, guide KYC verification, train staff, troubleshoot reporting and payout issues, monitor account health, and drive sustained transaction usage. Build relationships with district finance stakeholders and provide customer feedback to Product and Engineering.

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.

ParentSquare is seeking individuals to join their growing team in enhancing communication tools for schools and parents. The role involves promoting products that engage families and support educators.

Lead technical strategy and architecture as a Principal Software Engineer, define company-wide AI/LLM roadmap, drive platform reliability at scale, mentor senior engineers, and partner with executives and product to deliver secure, high-impact solutions.

Manage and grow organizational partner relationships to drive leads and product adoption. Coordinate partner marketing, enable sales with partner-related materials, assist finance with partner reporting, collaborate cross-functionally (sales, marketing, customer success), and identify and onboard new partnership opportunities to enhance ParentSquare usage.

Develop and ship backend and frontend features that improve school-family communication. Collaborate with product and design, champion AI/LLM-driven workflows, build scalable secure services on AWS, evolve monolithic systems, participate in code reviews, and help shape architecture.

Own a product line end-to-end: strategy, growth, retention, unit economics, and margin. Lead discovery, shape high-stakes bets, pitch leadership, and drive cross-functional execution. Partner with platform and Data/AI teams to build responsible AI workflows and scalable delivery while protecting engineering appetite and outcomes.