Frontline Education
Director, Client Success Management
🇺🇸 Hybrid - Naperville, IL
🕑 Full-Time
💰 $145K - $155K
💻 Customer Success
🗓️ September 10th, 2025
Gainsight
K-12
SaaS
Edtech.com's Summary
Frontline Education is hiring a Director, Client Success Management. The role involves leading client success strategy and operations, driving AI-enabled innovation, managing client retention and engagement, and building a high-performing team to deliver scalable value and revenue growth.
Highlights
- Define and execute client success strategies aligned with company goals.
- Lead integration of AI tools like predictive health scoring and renewal forecasting.
- Manage key escalations and foster senior-level client relationships.
- Directly lead and develop a team of Client Outcome Partners and Managers.
- Collaborate with Sales and Marketing for product expansion and upsell opportunities.
- Proven experience with tools such as Gainsight, Totango, Salesforce or similar.
- Required 8–10+ years in Client Success with 3–5+ years in senior leadership roles.
- Focus on operational excellence using analytics, automation, and real-time data.
- Salary range $145,000 - $155,000 plus bonus, personalized PTO, 401k match, health benefits, and tuition reimbursement.
- Serve K-12 education clients with a software platform supporting administration and analytics.
Director, Client Success Management Full Description
Director, Client Success Management
Location: Naperville, IL, United States
Description
Director, Client Success Management
Location Requirements: Hybrid to Wayne or Naperville. Remote candidates will be considered.
Your role on the team:
We are seeking a Director of Client Success Management who brings a bold, forward-thinking approach to customer engagement and lifecycle management. This individual will be responsible for architecting and executing a comprehensive strategy to ensure our clients realize measurable value, fueling both retention and expansion. The ideal candidate is a strategic operator and inspiring people leader who instills discipline, ownership, and accountability across the team, while actively championing an AI-first, innovation-driven culture. This leader must possess a strong bias for action, a passion for operational excellence, and a commitment to “driving value that drives demand.” They will empower their team to anticipate client needs, deliver high-impact engagements, and scale through technology and automation.
You can expect to:
Strategic Leadership
- Define and execute a client success strategy that aligns with company goals and enables scalable, value-driven outcomes across the client lifecycle.
- Establish a long-term vision that prioritizes innovation, digital transformation, and proactive client success practices.
- Serve as a thought leader in customer success strategy, continuously identifying new methods to elevate client value, reduce churn, and maximize lifetime value.
- Act as an executive sponsor for a defined subset of strategic accounts, fostering senior-level relationships and ensuring alignment between customer outcomes and business goals.
AI-Enabled Client Success
- Lead the integration of AI-powered tools and capabilities (e.g., predictive health scoring, automated engagement, sentiment analysis, renewal forecasting) to streamline operations and surface actionable insights.
- Champion an AI-first mindset across the Client Success organization, ensuring all team members are enabled to leverage emerging technologies to enhance client interactions and improve efficiency.
- Partner with cross-functional teams to design and implement intelligent workflows and automation that increase touchpoint consistency, accelerate time-to-value, and identify risk indicators earlier in the client journey.
Client Engagement & Retention
- Ensure all accounts have actionable success plans aligned to client goals, with consistent delivery of insights, value realization milestones, and ROI tracking.
- Own the framework for Executive Business Reviews (EBRs), ensuring strategic alignment with key stakeholders and executive sponsors.
- Personally manage key escalations and at-risk relationships while driving a culture of proactive resolution and customer advocacy.
Team Management & Development
- Directly lead and support a team of Strategic Client Outcome Partners and Client Outcome Managers, setting clear expectations, measurable objectives, and a standard of excellence.
- Hire, develop, and retain a high-performing team of client success professionals with a deep commitment to accountability, excellence, and continuous learning.
- Establish a feedback-driven culture rooted in transparency, empowerment, and results.
- Drive alignment across teams to ensure unified customer communication, seamless handoffs, and cross-functional execution.
Growth & Expansion
- Collaborate with Sales and Marketing to identify and drive opportunities for product expansion, adoption, and upsell within existing accounts.
- Ensure that value delivery is tightly coupled with demand generation efforts, enabling satisfied clients to become advocates and repeat buyers.
Operational Excellence & Innovation
- Design and optimize processes, playbooks, and engagement models tailored by customer segment, powered by technology and real-time data.
- Leverage analytics, AI, and automation to improve forecasting accuracy, streamline renewals, and optimize team capacity.
- Regularly evaluate new technologies and partner with Product and IT to pilot solutions that improve the client experience and internal efficiency.
Key Metrics / KPIs
- Gross Revenue Retention (GRR)
- Net Revenue Retention (NRR)
- Customer Health Score Accuracy & Predictive Engagement Rates
- Time-to-Value (TTV)
- Churn Rate
- Expansion Revenue / Product Adoption Growth
- Client Advocacy (e.g., NPS, referrals, testimonials)
What you bring to the role:
- Are a builder, not a maintainer—ready to architect a modern client success engine powered by data, technology, and innovation.
- Have a natural bias for action and operate with urgency and clarity, especially in complex or ambiguous situations.
- Lead with integrity, inspire accountability, and believe in coaching up, not managing down.
- Embrace change and challenge with a growth mindset, always seeking a better way.
- Understand that value delivered is what drives client demand—and you know how to operationalize that across an entire team.
Qualifications:
- 8–10+ years of experience in Client Success, Account Management, or Customer
- Experience, with 3–5+ years in a senior leadership capacity.
- Proven success leading scaled client success operations in a SaaS or technology-led organization.
- Demonstrated experience implementing or scaling AI-driven tools or customer success technologies such as Gainsight, Totango, Salesforce, or similar platforms.
- Deep understanding of the customer lifecycle, segmentation models, digital success strategies, and operational best practices.
- Track record of building high-performance teams, leading through change, and delivering measurable business outcomes.
- Highly analytical, with strong communication and executive presence.
- Passion for innovation, continuous improvement, and delivering exceptional client value at scale.
Who we are:
Frontline Education is a pioneer of school administration software purpose-built for K-12 districts. We provide innovative, connected solutions for student and special programs, business operations, and human capital management with powerful data and analytics to empower educators and administrators. We earn the trust of K-12 leaders across the U.S. by serving as a consistently high-performing, forthright partner of school districts through every dimension of the company.
We're a group of unique and talented individuals that love what we do. We've been lucky enough to land jobs with a rapidly growing tech company that supports an appreciative and friendly customer base. We work hard to make our customers happy, but we like to have a good time in the process. We are a company that strives to think in terms of “we” instead of “me.” We believe in the philosophy of servant leadership and that it’s all about putting others first. We also value the balance between family and work.
Frontline embraces diversity, equity, and inclusivity. We are intentionally building a workplace that respects, supports, and values the identities of all our employees. We believe this to be foundational in developing a strong community in our company. Frontline Education is an equal opportunity employer, and we do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.
The perks of being a Frontliner:
Frontline offers a competitive compensation package including a base salary, rewarding bonus structure, 401k match, ESPP, and personalized PTO! Our company growth has created a promising environment for career advancement and rewarding challenges. We offer a tuition reimbursement program for eligible college credit coursework available to employees depending on their status and length of employment.
The salary range for this role is $145,000 - $155,000 per year, based on experience, skills, and internal equity. In addition to base salary, this role includes a bonus, personalized PTO, and comprehensive benefits, including health insurance, 401k, and much more!
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