[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.ResponsibilitiesDevelop, 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 stagesOwn the planning, building, and maintenance of automated communication cadencesMonitor cadence performance (delivery, engagement, conversion) and keep journeys up to date as the product, messaging, and customer needs evolveBuild and manage calls to action (CTAs) and playbooks in Gainsight that drive participation, engagement, and adoptionTranslate complex product workflows into practical, confident user behaviorOwn 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 objectivesDevelop repeatable learning tracks (role-based, use-case-based, and maturity-based) that scale across the customer baseHost and facilitate engaging live learning experiencesAdapt 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 sessionsDevelop 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 contentEnsure learning content stays current with product releases and evolving best practicesManage program logistics end-to-end: scheduling, registration, reminders, attendance tracking, and post-session follow-upMaintain a consistent session calendar and communicate upcoming offerings to internal teams and customersEnsure 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 influenceGather qualitative feedback and apply learnings to continuously improve session content, delivery style, and journey sequencingSkills4+ years of experience in customer education, enablement, client success, training, or related rolesProven experience designing and delivering live, instructor-led learning for software usersStrong facilitation skills with confidence presenting to groups in virtual environmentsExcellent program management skills (planning, prioritization, execution)Strong written communication and ability to translate product complexity into clear learning outcomesExperience managing digital customer journeys, nurture campaigns, or lifecycle outreachHands-on experience with Gainsight, including CTAs, playbooks, and journey orchestrationExperience in SaaS, B2B software, or technology-driven environmentsFamiliarity with adult learning principles, instructional design, and engagement best practicesExperience supporting mid-market and/or enterprise customersBenefitsHealth 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 DisabilityTraining & DevelopmentWork From HomeWellness ResourcesCompany OverviewLEAP is a Case management & Accounting software committed to consistently providing world-class practice management software. It was founded in 1992, and is headquartered in Edinburgh, Edinburgh, City of, GBR, with a workforce of 501-1000 employees. Its website is https://www.leaplegalsoftware.com/.