Client Success Learning Program Manager

LEAP Legal Software

4d•$115,000 - $140,000•Remote

About The Position

This role is designed for someone who enjoys helping others understand complex tools. The Client Success Learning Program Manager will teach small law firms using LEAP how to maximize its benefits and will develop a program to scale these successes to thousands of firms. The position involves leading the planning, execution, and growth of scalable learning and adoption programs for existing LEAP users. The goal is to help customers improve their proficiency, adopt more features, and consistently derive value through a combination of live learning sessions (webinars, bootcamps, office hours) and digital communication throughout their lifecycle. This is a new, high-impact role focused on scaling best practices that were previously delivered on a one-to-one basis. The individual will build upon a recently launched learning program, managing both live learning delivery and the operationalization of automated outreach across the customer journey using Gainsight. Collaboration with Client Success leadership, Client Success Managers, Product, Support, and internal subject matter experts is crucial to ensure customers receive timely and relevant learning with clear calls to action that promote adoption, satisfaction, and retention.

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

Nice To Haves

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

Responsibilities

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.
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).
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, and post-session resources and follow-up content.
Ensure learning content stays current with product releases and evolving best practices.
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).
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, and retention and expansion influence.
Gather qualitative feedback and apply learnings to continuously improve session content, delivery style, and journey sequencing.