Jobs at ParentSquare, Inc

Own positioning, messaging, and go-to-market strategy for ParentSquare Attendance Plus. Build attendance-market expertise, lead product launches, define success metrics, conduct customer and win/loss research, support sales enablement, and influence packaging, pricing, and roadmap decisions. Partner cross-functionally with Product, Sales, Customer Success, and Marketing to expand adoption within existing districts and reach new school district customers. The role is fully remote and requires approximately 20% travel to conferences and customer events.

Own a hybrid portfolio of charter school customers, including enterprise networks and smaller sites. Build success plans, drive adoption and ROI, manage renewals and retention, resolve escalations, support implementations, and identify expansion opportunities. Lead scaled onboarding, product demonstrations, training, workshops, and user groups while collaborating with Sales, Support, Implementation, Product, and Finance. Serve as the primary relationship owner and advocate for charter customers.

Conduct high-volume outbound calls and targeted email outreach to school and district accounts, respond to inbound leads, qualify prospects, book at least five demos weekly, maintain accurate CRM records, deliver scripted product demos, and hand qualified opportunities to sales teams. The role is metrics-driven and includes structured coaching toward a future closing-sales position.

Own end-to-end product design for a major education platform area, from discovery and problem framing through implementation. Translate complex workflows into accessible, multilingual web and mobile experiences; conduct usability research; contribute to design systems; prototype with AI tools; design understandable AI features; collaborate with product, engineering, research, customer success, and support; present design decisions; and mentor other designers.

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 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.

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.

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.