Client Success Enablement Manager

Skai; Chicago (IL); On-site; USD 100,000 - 140,000; Full time

Benefits offered by this job

Professional growth stipend

Stock option plan

Health and wellness initiatives

Diversity and inclusion programs

Job summary

Skai in Chicago, IL is seeking a Client Success Enablement professional to design and deliver engaging learning experiences that empower our CS teams to succeed.

You will translate business priorities into practical training, collaborate with CS leadership and cross-functional partners, and build onboarding paths, playbooks, and AI-enabled workflows to improve customer engagement.

Qualifications

• 2–4 years in Customer Success or Enablement.
• Experience in B2B SaaS or advertising tech.
• Strong communication and facilitation skills.
• Ability to build trusted relationships across functions.

Responsibilities

• Design and deliver CS enablement programs and onboarding.
• Develop live and virtual training sessions, workshops, and role plays.
• Create customer-facing frameworks, playbooks, and coaching tools.
• Partner with CS leadership to identify performance gaps and translate priorities.
• Track program participation and feedback to drive improvements.
• Support product launches with training and seller resources.

Skills

data driven

curious

results oriented

interpersonal skills

relationship-building

project management

communication skills

stakeholder management

Tools

Salesforce

Clari

Highspot

LMS

Job description

• In this role, you’ll help design and deliver engaging learning experiences that equip our Client Success teams with the skills, knowledge, and confidence to succeed
• You’ll work closely with CS leadership and cross-functional partners to turn business priorities into practical training, resources, and development programs that make a real difference in how our teams engage with customers
• Reporting to the Director of Revenue & Client Enablement, this is an ideal opportunity for someone who has experience in Client Success and is ready to take greater ownership of programs, content, onboarding, and stakeholder relationships
• You do not need to have done everything before. We are looking for someone with a bias to action who is data driven, curious, results-oriented, and has exceptional interpersonal and relationship-building skills
• Support the development and execution of global CS enablement programs focused on consultative discovery, value realization, strategic account management, executive engagement, retention, and growth
• Turn complex information into clear, practical, and engaging learning experiences, including live in-person and virtual training sessions, interactive workshops, role plays, and certifications
• Create and maintain customer-facing frameworks, talk tracks, meeting guides, account planning resources, coaching tools, and AI workflows that help reps engage customers more strategically
• 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
• Help reinforce new behaviors after training through manager coaching resources, peer learning, call reviews, practice activities, and ongoing inspection
• Partner with Product Marketing to support the rollout of product launches, new capabilities, and go-to-market initiatives through training facilitation, communications, and seller resources
• Bring recommendations, identify opportunities to improve the learner 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
• Bring recommendations, identify opportunities to improve the learner and seller experience, and communicate progress, risks, and decisions clearly

Benefits

• Offices in cities across the world
• Professional growth stipend
• Diversity and inclusion programs
• Company outings and volunteering
• Health and wellness initiatives
• Stock option plan
• Transportation benefits
• Exclusive perks and discounts
• Stocked kitchens and happy hours

AI curiosity and proficiency. Including being comfortable using AI to automate workflows, or building new AI workflows to improve sales processesIntellectual curiosity and the ability to quickly learn new products, industries, systems, and commercial conceptsA proactive mindset and willingness to take ownershipExperience partnering across multiple stakeholders and cross-functional teamsStrong project management and organizational skills, with the ability to manage multiple workstreams and follow through on detailsApproximately 2-4 years of relevant professional experience, including experience in Customer Success, Customer Success Enablement, Learning & Development, Account Management, or a related fieldExperience in a B2B sales or customer-facing organization, preferably within SaaS, advertising technology, marketing technology, digital media, or another complex businessAbility to build trusted relationships and work effectively across functions, roles, and levels of seniorityStrong communication and facilitation skills, with the ability to make complex ideas easy to understand and deliver sessions that are interactive, relevant, and memorablePrior experience in a customer-facing role, including Customer Success, Account Management, or SalesExposure to consultative selling, value-based customer engagement, account planning, or customer success methodologiesExperience with Salesforce, Clari, Highspot, learning management systems, or similar toolsFamiliarity with digital advertising, paid search, paid social, retail media, commerce media, or programmatic advertisingExperience creating or maintaining training materials, onboarding resources, playbooks, or internal communicationsA clear and engaging communication style, with the ability to make difficult concepts approachable and bring energy to both virtual and in-person training