Director of Customer Success

What You’ll Do

• Customer Segmentation Oversight: Lead and refine customer success strategies for three distinct customer segments (enterprise, mid-market, SMB), ensuring tailored approaches for retention, satisfaction, and growth across all tiers.
• Customer Journey Mapping: Develop and optimize comprehensive customer journey maps that outline the end-to-end customer experience. Use journey mapping to identify key touchpoints, reduce friction, and align internal teams around key milestones in the customer lifecycle.
• Onboarding & Adoption: Oversee and continually optimize the onboarding process in collaboration with Product and Sales teams. Ensure a seamless customer journey from sales to onboarding and ongoing adoption by building structured, customer-centric onboarding experiences.
• Success Plans & Playbooks: Build and continuously optimize customer success plans and playbooks for each segment. These will serve as strategic guides for Customer Success Managers (CSMs) to deliver value, track progress, and manage customers’ success effectively at scale.
• Digital Customer Success Models:D esign and implement scalable digital customer success models, leveraging self-service resources, automation, and digital touchpoints to drive efficiency and optimize customer engagement across all tiers, particularly for the SMB segment.
• Renewals & Expansion Revenue: Own the customer renewal lifecycle, working closely with Sales and Account Management teams to identify upsell/cross-sell opportunities. Drive expansion revenue through proactive management of success plans and regular value delivery, ensuring optimal NRR and GRR.
• Customer Health & Success Metrics: Utilize customer health data from CS tools like Gainsight to monitor risks and opportunities. Develop and execute strategies to improve key metrics such as NRR, GRR, NPS, and CSAT, while ensuring regular reporting to executive leadership.
• Cross-Departmental Collaboration:Product: Partner with the Product team to align the roadmap with customer feedback and success metrics, ensuring that new features and improvements are customer-driven.
• Sales: Work closely with Sales to align on account strategy, ensuring a smooth transition between Sales and Customer Success teams, and supporting sales with customer insights and opportunity tracking.
• Marketing: Collaborate with Marketing to build customer advocacy programs, success stories, and campaigns that strengthen the customer community and drive further engagement.
• Care/Support: Ensure close alignment with Care/Support teams, focusing on swift issue resolution and improved student satisfaction KPIs.
• Finance/Accounting: Partner with Finance and Accounting to forecast and track renewal and expansion revenue, ensuring alignment with financial targets.
• Salesforce & Opportunity Creation: Collaborate with Sales and Account Management to manage and track customer opportunities within Salesforce, maintaining a unified approach to account management and growth initiatives.
• Team Leadership & Development: Lead a high-performing team of Customer Success Managers (CSMs) across all customer segments. Provide mentorship, strategic guidance, and performance management to ensure consistent outcomes in customer retention, satisfaction, and expansion.

What You Bring

• SaaS Leadership Experience: Minimum of 7+ years in a Customer Success leadership role within the SaaS industry, with a proven record of managing customer retention and driving growth.
• Education: Bachelor's degree in Business Administration, Marketing or other relevant field is required
• Expansion and Relationship Heavy Focus: Minimum of 5+ years leading Customer Success teams including Enterprise customer segment.
• CS Tools: Proficiency with CS platforms (e.g., Gainsight) and CRM systems like Salesforce, with experience in opportunity creation, customer health scoring, and managing the full customer lifecycle.
• Customer Journey & Success Plans: Experience in developing and optimizing customer journey maps, creating data-driven success plans, and designing playbooks to ensure repeatable and scalable customer success processes.
• Digital Customer Success Models: Proven ability to build and optimize digital customer success models that enable scalability and efficiency through automation, self-service, and proactive engagement.
• Metrics-Driven Approach: Deep understanding and hands-on experience with key success metrics (NRR, GRR, NPS, CSAT) and the ability to execute strategies that improve them.
• Cross-Functional Leadership: Demonstrated ability to work cross-functionally with Product, Sales, Marketing, Care, and Finance/Accounting teams to drive comprehensive customer success strategies.
• Account Management Model: Experience working within an account management model in Customer Success, with a focus on collaboration, growth, and shared goals.

Preferred Qualifications

• Working within Higher Education- Stakeholders/ Procurement a plus.
• Strong strategic thinking with the ability to balance long-term vision with short-term execution.
• Excellent communication and presentation skills, with experience influencing executive leadership and key stakeholders.
• Experience in building digital and self-service strategies to support scalable growth.

Benefits + Perks

• Paid Company Holidays + No work on your birthday!
• Flexible PTO + Volunteer Time Off (VTO) as an organization to give back to the community
• Variable bonus eligibility on a quarterly basis
• Company-sponsored Health Insurance (Medical, Dental, Vision) + Pet Insurance 
• Company-paid group Life Insurance + Company-paid Short Term Disability
• Concierge benefit support services
• 401(k) with employer match 
• Free access to TimelyCare virtual medical and mental health support for you and your immediate family
• Mission-Driven Purpose with a Supportive Team Culture