Enterprise Customer Success Manager - Central or East Coast

The Enterprise Customer Success Manager (CSM) will own the success, retention, and growth of a portfolio of Gaggle’s largest and most strategic district partners, primarily located across the Central and Eastern United States.

This individual will serve as a strategic advisor to district leaders, helping customers achieve meaningful outcomes tied to student safety, well-being, product adoption, and overall program impact. The Enterprise CSM will develop a deep understanding of each district’s priorities, organizational structure, and success measures and will proactively align Gaggle’s products, services, and resources to those needs.

This role requires a thoughtful balance of enterprise relationship management, strategic customer success, operational execution, and retention and growth accountability. The Enterprise CSM will build trusted relationships across multiple levels of district leadership, guide complex implementations and initiatives, identify risk and expansion opportunities, and lead customers through the full lifecycle of their partnership with Gaggle.

The Enterprise CSM will work cross-functionally with Product, Sales, Safety, Therapy, Implementation, Marketing, Implementation, and Support to ensure customers receive a consistent, high-quality experience and that customer feedback and needs are represented internally.

This role reports to the Manager, Customer Success Team.

• Own the overall success, health, retention, and growth of an assigned portfolio of Enterprise customers.
• Serve as the primary strategic point of contact for assigned districts, developing trusted relationships with executive leadership and key stakeholders across departments.
• Establish customer success plans through consultative conversations that connect district goals, stakeholder priorities, product utilization, and measurable outcomes.
• Develop relationships across multiple levels and departments within each district to create strong, sustainable partnerships that are not dependent on a single stakeholder.
• Maintain a deep understanding of each customer’s organizational structure, priorities, initiatives, funding considerations, and decision-making processes.
• Proactively identify areas of risk, opportunity, or misalignment and develop clear action plans to address them.
• Provide internal teams with meaningful insights into customer needs, challenges, feedback, and opportunities to improve Gaggle’s products, services, and overall customer experience.

• Lead regular strategic conversations with customers focused on outcomes, adoption, program performance, emerging needs, and opportunities to increase the value of their partnership with Gaggle.
• Use customer health, product utilization, safety, and engagement data to identify trends and provide meaningful recommendations to district leaders.
• Drive adoption across purchased products and services by ensuring district stakeholders understand how to effectively integrate Gaggle into their student safety and well-being strategies.
• Share best practices, recommendations, and relevant insights based on Gaggle’s work with districts across the country.
• Educate customers on new products, features, functionality, and services that may support their evolving needs.
• Coordinate appropriate training, professional development, and strategic resources for district stakeholders.
• Partner cross-functionally to manage complex customer initiatives, escalations, product needs, and implementations through resolution.

• Own the end-to-end renewal strategy and process for assigned customers with direct accountability for retention.
• Develop a strong understanding of each district’s budgeting, procurement, funding, and approval processes, including key stakeholders, timelines, and potential barriers to renewal.
• Build renewal strategies well in advance of contract expiration and proactively address risks that could impact retention.
• Maintain accurate forecasting and visibility into the renewable book of business.
• Partner closely with Sales to identify and support appropriate expansion opportunities based on customer goals, needs, and product utilization.
• Ensure renewal and expansion conversations remain grounded in customer outcomes and the long-term value of the partnership.

• Provide strategic oversight for large or complex implementations within assigned accounts, ensuring alignment between customer expectations, timelines, internal teams, and desired outcomes.
• Partner with Implementation, Product, Safety, Therapy, Implementation, Support, and Sales to coordinate resources and provide customers with a cohesive experience.
• Help establish clear ownership, timelines, success measures, and communication plans for major customer initiatives.
• Navigate complex or challenging customer situations with confidence, professionalism, and sound judgment.
• Advocate internally for customer needs while balancing customer expectations with organizational priorities and capabilities.

• 7+ years of experience in Customer Success, Account Management, or a related field managing Enterprise or strategic accounts.
• Proven ability to own a diverse book of business with direct accountability for customer retention and growth.
• Demonstrated experience managing complex, large-scale implementations or customer initiatives involving multiple teams and stakeholders.
• Prior experience working within K–12 education, with a strong understanding of district structures, priorities, operational realities, and decision-making processes.
• Exceptional consultative skills with the ability to build credibility and trusted relationships with senior district leadership, including superintendent, cabinet, technology, student services, safety, and other executive-level stakeholders.
• Demonstrated ability to navigate complex, multi-stakeholder organizations and build alignment across departments with differing priorities.
• Experience navigating budgeting, procurement, funding, and renewal processes, ideally within the K12 education sector.
• Ability to confidently provide strategic direction, navigate difficult conversations, manage pushback, and guide customers toward successful outcomes.
• Strong analytical skills with the ability to translate customer, utilization, and program data into meaningful recommendations and action plans.
• Highly organized and self-directed, with strong account planning, prioritization, time management, and territory management skills.
• Proven ability to collaborate effectively in a cross-functional, team-based organization.
• Ability and willingness to travel regularly to support strategic customers, onsite meetings, implementations, trainings, and industry events.

• Experience supporting large school districts 
• Experience managing relationships across multiple district departments and executive stakeholder groups.
• Experience with student safety, student well-being, educational technology, or SaaS solutions.
• Bachelor’s degree.
• Proficiency with Salesforce

Location & Travel

This is a remote, work-from-home position supporting a customer portfolio primarily located across the Central and Eastern United States.

Because of the geographic concentration of the customer base, candidates located in the Central or Eastern Time Zone are strongly preferred. The role requires flexibility to align working hours with customer needs, as well as occasional travel throughout the assigned territory. 

A reliable high-speed internet connection and a comfortable, private, dedicated workspace are required for success in this role