Jobs at ParentSquare, Inc

Leads ParentSquare and Remind websites, overseeing roadmap, updates, SEO/AEO, site performance, conversion testing, agency partnerships, and campaign launches. Maintains brand consistency across web and marketing materials, develops self-serve brand templates, manages the marketing design team, and uses AI tools for creative production. Partners with Product Marketing, Communications, RevOps, Legal, Product Ops, and AI teams to support growth and K-12 privacy standards.

Lead ParentSquare’s growth and lifecycle marketing engine across audience growth, content, demand generation, email, events, customer journeys, expansion, and advocacy. Manage managers and specialists across multiple marketing disciplines, drive measurable pipeline and revenue, establish segmentation and measurement frameworks, and partner with Product Marketing, Customer Success, Sales, RevOps, Legal, and Security. The role requires strategic leadership alongside hands-on campaign and lifecycle execution in a SaaS environment.

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.

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.

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.

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.

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.