Client Success Learning Program Manager

Job Description

If you love the moment a complicated tool finally clicks for someone, this role is built for you: you'll teach the small law firms who run on LEAP to get the most from it — and design the program that turns those one-to-one wins into something thousands of firms feel.

The Client Success Learning Program Manager leads the planning, execution, and growth of scalable learning and adoption programs for existing LEAP users. This role is responsible for helping customers deepen proficiency, adopt additional features, and consistently realize value through a mix of live learning (webinars, bootcamps, office hours) and digital lifecycle outreach.

This is a net-new, high-impact role designed to scale best practices that have historically been delivered 1:1. You will build on a newly launched learning program and own both how learning is delivered live and how automated outreach is operationalized across the customer journey using Gainsight.

You’ll collaborate closely with Client Success leadership, Client Success Managers, Product, Support, and internal subject matter experts to ensure customers receive the right learning at the right time with clear calls to action that drive adoption, satisfaction, and retention.

The OTE range for this position sits between USD $115,000-140,000 dependent upon experience.

Key Responsibilities

Digital Customer Journey & Automated Communication Ownership (Gainsight)

• Develop, manage, and continuously improve the Client Success digital client lifetime journey touchpoints with customer success motions within Gainsight, ensuring customers receive timely, relevant outreach across lifecycle stages.
• Own the planning, building, and maintenance of automated communication cadences.
• Monitor cadence performance (delivery, engagement, conversion) and keep journeys up to date as the product, messaging, and customer needs evolve.
• Build and manage calls to action (CTAs) and playbooks in Gainsight that drive participation, engagement, and adoption.

Live Learning Program Planning & Execution

• Translate complex product workflows into practical, confident user behavior.
• Own the roadmap for Client Success live learning programs across the post-onboarding lifecycle (adoption, optimization, feature expansion, renewal readiness).
• Define learning goals and session priorities aligned to customer outcomes and product adoption objectives
• Develop repeatable learning tracks (role-based, use-case-based, and maturity-based) that scale across the customer base

• Host and facilitate engaging live learning experiences
• Adapt delivery to different audiences (admins, end users, power users, leaders)

SME Collaboration & Curriculum Development

• Partner with internal subject matter experts (CSMs, Product, Support, Implementation, Ops) to co-create and deliver sessions
• Develop and maintain:
• Facilitator guides and session run-of-show
• Slide decks and demos
• Exercises, practice workflows, and supporting handouts
• Post-session resources and follow-up content
• Ensure learning content stays current with product releases and evolving best practices

Program Operations & Delivery Management

• Manage program logistics end-to-end: scheduling, registration, reminders, attendance tracking, and post-session follow-up
• Maintain a consistent session calendar and communicate upcoming offerings to internal teams and customers
• Ensure operational excellence across platforms (webinar tools, CRM/Gainsight, learning repository)

Measurement, Reporting & Optimization

• Define success metrics and dashboards for both live learning and digital outreach, including:
• Attendance and completion rates
• Engagement and satisfaction scores
• Feature adoption lift
• Reduction in repeat support needs
• Retention and expansion influence
• Gather qualitative feedback and apply learnings to continuously improve session content, delivery style, and journey sequencing

Requirements

• 4+ years of experience in customer education, enablement, client success, training, or related roles
• Proven experience designing and delivering live, instructor-led learning for software users
• Strong facilitation skills with confidence presenting to groups in virtual environments
• Excellent program management skills (planning, prioritization, execution)
• Strong written communication and ability to translate product complexity into clear learning outcomes

Preferred

• Experience managing digital customer journeys, nurture campaigns, or lifecycle outreach
• Hands-on experience with Gainsight, including CTAs, playbooks, and journey orchestration
• Experience in SaaS, B2B software, or technology-driven environments
• Familiarity with adult learning principles, instructional design, and engagement best practices
• Experience supporting mid-market and/or enterprise customers

Core Competencies

• Confident facilitator and strong storyteller
• Operationally excellent and detail-oriented
• Customer-first mindset
• Cross-functional collaborator who can influence without authority
• Data-informed decision maker

Benefits

• Health Care Plan (Medical, Dental & Vision)
• Retirement Plan (401k, IRA)
• Life Insurance (Basic, Voluntary & AD&D)
• Paid Time Off (Vacation, Sick & Public Holidays)
• Family Leave (Maternity, Paternity)
• Short Term & Long Term Disability
• Training & Development
• Work From Home
• Wellness Resources

LIFE @ LEAP

LEAP is all about impact, growth and ownership. We’re united by a genuine passion for what we do, enriched by the care we show to our customers and each other and driven by the difference we can make together.

LEAPster culture is about prioritizing and celebrating the incredible humans behind our market-leading technology. Think performance-driven incentives, flexible remote work, a generous Parenting Policy, and so much more.

We strongly believe that mutual trust, personal development and career progression are at the heart of a healthy, high-performing culture and we’re committed to empowering LEAPsters with resources, and ongoing support to define a career with us. With us, your career will grow as you do, with opportunities to step into new roles, and explore new departments in this innovative industry.

We are an equal opportunities employer and welcome applications from all suitably qualified persons regardless of their race, sex, disability, religion/belief, sexual orientation or age. All LEAP employees must ensure ongoing compliance with organizational security policies, standards, procedures, and control frameworks including risk management and incident management processes.