[Remote] Client Success Learning Program Manager

Note: The job is a remote job and is open to candidates in USA. LEAP Legal Software is looking for a Client Success Learning Program Manager to enhance the learning experience for small law firms using their software. This role involves leading scalable learning programs, collaborating with various teams to deliver effective training, and ensuring customer engagement and satisfaction through automated outreach and live learning sessions.

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, 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, Retention and expansion influence
• Gather qualitative feedback and apply learnings to continuously improve session content, delivery style, and journey sequencing

Skills

• 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
• 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

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

Company Overview