Client Success Learning Program Manager

Role overview

This position is for someone who enjoys helping users move from confusion to confidence. You will support small law firms using LEAP by creating a learning experience that helps them get more value from the platform, while also shaping a scalable program that extends those successes to a much larger customer base.

The Client Success Learning Program Manager is responsible for planning, running, and expanding learning and adoption initiatives for current LEAP customers. The focus is on increasing product proficiency, encouraging use of additional features, and driving ongoing value through live education sessions such as webinars, bootcamps, and office hours, along with automated lifecycle communication.

This is a newly created, high-impact position meant to scale practices that were previously handled one customer at a time. You will help extend a newly introduced learning program and own both the live learning experience and the automated customer outreach workflow within Gainsight.

You will work closely with Client Success leadership, Client Success Managers, Product, Support, and internal subject matter experts to ensure customers receive the right guidance at the right time, with clear next steps that support adoption, satisfaction, and retention.

The total on-target earnings range for this position is USD $115,000 to $140,000, depending on experience.

Digital customer journey and automation

• Design, maintain, and improve lifecycle communication touchpoints in Gainsight so customers receive timely and relevant messaging across different stages of their journey.
• Take ownership of automated outreach cadences, including planning, setup, and ongoing updates.
• Track how each cadence performs in terms of delivery, engagement, and conversion, and adjust journeys as the product, messaging, and customer needs change.
• Create and manage CTAs and playbooks in Gainsight that encourage participation, usage, and adoption.

Live learning program design and delivery

• Turn complex product processes into practical guidance that helps users work with confidence.
• Own the live learning roadmap across the post-onboarding lifecycle, including adoption, optimization, feature expansion, and renewal readiness.
• Set learning objectives and prioritize sessions based on customer outcomes and adoption goals.
• Build reusable learning tracks that can be tailored by role, use case, and customer maturity level.
• Lead and present engaging live learning sessions.
• Adjust facilitation style for different audiences such as administrators, end users, advanced users, and leaders.

Curriculum development and SME collaboration

• Work with internal experts across Client Success, Product, Support, Implementation, and Operations to create and deliver learning content.
• Develop facilitator notes and session run-of-show materials.
• Create presentation decks and product demonstrations.
• Prepare exercises, practice workflows, and support handouts.
• Produce follow-up materials and post-session resources.
• Keep learning content aligned with product updates and evolving best practices.

Program operations and delivery

• Handle end-to-end program logistics, including scheduling, registration, reminders, attendance tracking, and post-session follow-up.
• Maintain a regular session calendar and keep internal teams and customers informed about upcoming programs.
• Ensure smooth execution across the tools used for webinars, CRM/Gainsight, and the learning repository.

Measurement and optimization

• Define success measures and dashboards for both live learning and digital outreach.
• Monitor attendance, completion, engagement, satisfaction, feature adoption lift, reduction in repeat support requests, and influence on retention and expansion.
• Collect feedback from customers and internal teams, then use it to improve content, delivery, and journey sequencing.

Requirements

• At least 4 years of experience in customer education, enablement, client success, training, or a closely related field.
• Background in designing and delivering live, instructor-led learning for software users.
• Strong group facilitation ability and comfort presenting in virtual settings.
• Solid program management capabilities, including planning, prioritization, and execution.
• Excellent writing skills and the ability to explain complex product concepts in simple learning terms.

Preferred background

• Experience with digital customer journeys, nurture campaigns, or lifecycle outreach.
• Direct hands-on experience with Gainsight, including CTAs, playbooks, and journey orchestration.
• Experience in SaaS, B2B software, or other technology-focused environments.
• Knowledge of adult learning principles, instructional design, and engagement strategies.
• Experience supporting mid-market and/or enterprise customers.

Core strengths

• Confident presenter with strong storytelling ability.
• Highly organized and detail-focused.
• Customer-first mindset.
• Effective cross-functional partner who can influence without formal authority.
• Uses data to guide decisions and improvements.

Benefits and additional information

• Medical, dental, and vision coverage.
• Retirement options including 401(k) and IRA.
• Life insurance, including basic, voluntary, and AD&D coverage.
• Paid time off for vacation, sick leave, and public holidays.
• Family leave, including maternity and paternity leave.
• Short-term and long-term disability coverage.
• Training and development support.
• Work-from-home flexibility.
• Wellness resources.

The company emphasizes impact, growth, and ownership, with a culture built around caring for customers and colleagues while making a meaningful difference together. The environment includes performance-driven incentives, flexible remote work, and a generous parenting policy. There is also a strong focus on trust, personal development, and career progression, with opportunities to move into new roles or explore different departments.

The organization is an equal opportunity employer and welcomes applications from all qualified candidates regardless of race, sex, disability, religion or belief, sexual orientation, or age.

All employees are expected to comply with organizational security policies, standards, procedures, and control frameworks, including risk management and incident management processes.