Client Success Enablement Manager

Skai•Chicago, IL

10h•$95,000 - $105,000•Hybrid

About The Position

Skai is seeking a Client Success Enablement Manager to help transform how its Client Success organization engages with customers through a proactive, consultative, and value-driven approach. The role designs and delivers learning experiences that build Client Success teams’ skills and confidence, partnering with CS leadership and cross-functional teams to turn business priorities into practical training, resources, and development programs. Reporting to the Director of Revenue & Client Enablement, the position supports global enablement programs and CS onboarding, creates customer-facing and internal resources, reinforces behaviors after training, and supports product launches and go-to-market initiatives. The role tracks participation, engagement, feedback, skill development, and other effectiveness indicators, using data and qualitative feedback to improve programs. The position is suited to someone with relevant customer success or related experience who is ready to take ownership of programs, content, onboarding, and stakeholder relationships.

Requirements

Approximately 2–4 years of relevant professional experience in Customer Success, Customer Success Enablement, Learning & Development, Account Management, or a related field.
Experience in a B2B sales or customer-facing organization; SaaS, advertising technology, marketing technology, digital media, or another complex business is preferred.
AI curiosity and proficiency, including comfort using AI to automate workflows or build new AI workflows to improve sales processes.
Strong communication and facilitation skills, including the ability to explain complex ideas clearly and deliver interactive, relevant, memorable sessions.
Strong project management and organizational skills, with the ability to manage multiple workstreams and follow through on details.
Proactive mindset and willingness to take ownership.
Experience partnering with multiple stakeholders and cross-functional teams.
Ability to build trusted relationships and work effectively across functions, roles, and levels of seniority.
Intellectual curiosity and ability to quickly learn new products, industries, systems, and commercial concepts.

Nice To Haves

Prior experience in a customer-facing role, including Customer Success, Account Management, or Sales.
Exposure to consultative selling, value-based customer engagement, account planning, or customer success methodologies.
Experience with Salesforce, Clari, Highspot, learning management systems, or similar tools.
Familiarity with digital advertising, paid search, paid social, retail media, commerce media, or programmatic advertising.
Experience creating or maintaining training materials, onboarding resources, playbooks, or internal communications.
Clear and engaging communication style, with the ability to make difficult concepts approachable and bring energy to virtual and in-person training.

Responsibilities

Support the development and execution of global CS enablement programs covering consultative discovery, value realization, strategic account management, executive engagement, retention, and growth.
Turn complex information into practical, engaging learning experiences, including in-person and virtual training, workshops, role plays, and certifications.
Create and maintain customer-facing frameworks, talk tracks, meeting guides, account planning resources, coaching tools, and AI workflows.
Design, manage, and deliver CS onboarding programs, including role-based learning paths, practical application, and certification.
Partner with CS leadership to identify performance gaps, gather field insights, and translate business priorities into targeted enablement initiatives.
Reinforce new behaviors after training with manager coaching resources, peer learning, call reviews, practice activities, and ongoing inspection.
Partner with Product Marketing on product launches, new capabilities, and go-to-market initiatives through training facilitation, communications, and seller resources.
Recommend improvements to the learner and seller experience and CS effectiveness, and communicate progress, risks, and decisions clearly.
Track program participation, content engagement, learner feedback, skill development, and other indicators of effectiveness; use data and qualitative feedback to recommend improvements.