Senior Customer Success Manager, Enterprise Accounts

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Role: Senior Customer Success Manager, Enterprise Accounts
Location: SmarterX HQ (Cleveland)
Reports To: VP of Customer Success / COO

About SmarterX

SmarterX is an AI transformation company. We educate and empower leaders to reimagine business models, reinvent industries, and rethink what's possible. 

  • We believe AI will rapidly transform businesses, industries, jobs, the economy, educational systems, and society. 
  • We believe you can build a smarter version of any business through a responsible, human-centered approach to AI.
  • We believe the future of all business is AI native, AI emergent, or obsolete.  
  • We believe AI education and training is the foundation for success in every organization.

Our goal is to Accelerate AI Literacy for All through courses, content and events. Consulting and speaking are also secondary solutions under the SmarterX brand.

SmarterX has three primary public-facing business units and brands:

  • Marketing AI Institute: Media, event and education business founded in 2016 that is designed to make AI approachable and actionable for marketers. The Institute has more than 100,000 contacts, and its flagship in-person conference, MAICON, draws 2,000+ marketers to Cleveland each year. 
  • AI Academy by SmarterX: Originally launched in 2020 under the Marketing AI Institute brand, AI Academy is being spun off as a dedicated site and brand. AI Academy is a high-growth business unit designed to prepare individuals and organizations for the future of work by making AI education accessible and personalized.
  • The Artificial Intelligence Show: The podcast is SmarterX’s fastest growing media channel with 115,000+ downloads per month. The podcast serves as a promotional tool and lead generator for SmarterX and its business units. 

SmarterX also has an internal AI Content Studio that supports audience growth, demand generation, and customer success across all brands / business units. The AI Content Studio produces blog posts, books, blueprints, courses, newsletters, podcasts, presentations, research, videos and webinars.

Role Overview

The Senior Customer Success Manager (SCSM), Enterprise Accounts is responsible for the success, growth, and retention of AI Academy’s premium and enterprise customers. These accounts typically include 100+ licenses or high-growth potential, and each SCSM manages a portfolio of $2–$3M in ARR.

This role is far more than traditional customer success. SCSMs function as AI Transformation Consultants, acting as the primary point of contact and customer champion. You will guide organizations through onboarding, adoption, enablement, expansion, and renewal—ensuring measurable impact from their AI Academy investment.

Key Responsibilities

Enterprise Customer Ownership

  • Serve as the primary relationship owner for a portfolio of enterprise and premium business accounts.
  • Act as the internal advocate for customer needs, priorities, and success outcomes.
  • Build trusted, long-term relationships with executive sponsors, transformation leaders, and enablement teams.

Onboarding & Adoption

  • Lead structured onboarding for enterprise customers, including stakeholder alignment and success planning.
  • Design and execute employee rollout and internal communications plans.
  • Provide orientation sessions, welcome communications, and resources to help members maximize their learning experience.
  • Track onboarding success metrics and make improvements as needed
  • Establish success criteria, adoption milestones, and early wins.

AI Transformation Consulting

  • Conduct AI Transformation Score assessments to benchmark customer readiness and progress.
  • Partner with customers on goal setting and learning journey development aligned to business objectives.
  • Provide strategic guidance on AI literacy, use-case adoption, and workforce enablement.

Customer Enablement & Engagement

  • Deliver personalized support tailored to enterprise needs.
  • Serve as the primary point of contact for AI Academy members, delivering clear and proactive communication.
  • Manage communications to keep members informed and engaged.
  • Provide customer enablement support including:
    • Training webinars
    • Office hours
    • Executive and team workshops
    • Playbooks and best-practice guidance
  • Lead monthly and quarterly transformation review meetings with key stakeholders.

Customer Inquiries & Support

  • Respond to and resolve member inquiries in a timely and professional manner.
  • Work closely with internal teams to address technical issues, course-related questions, and membership concerns.
  • Identify common challenges and develop scalable solutions to enhance customer satisfaction.

Utilization Monitoring & Reporting

  • Monitor and analyze learner engagement and utilization, including:
    • Course enrollments and completions
    • Weekly active users
    • Learning hours
    • Badges and certifications earned
  • Translate data into actionable insights and recommendations for customers.
  • Provide regular reporting and executive-ready summaries.

Expansion & Renewal Management

  • Own expansion and renewal strategy for assigned accounts.
  • Identify opportunities to grow usage, licenses, certifications, and programs.
  • Partner with Sales and Leadership on contract renewals and account growth.
  • Ensure renewal readiness through strong adoption, value realization, and executive alignment.

AI Agent Management

  • Leverage AI agents to support customer communications, reporting, and insights.
  • Ensure AI agents are trained with up-to-date customer, product, and research information.
  • Continuously refine AI-powered workflows to enhance customer experience and efficiency.

Qualifications & Experience

  • 6–10+ years of experience in Customer Success, Account Management, Consulting, or Enablement, preferably with enterprise SaaS or eLearning accounts.
  • Proven success managing $2M+ ARR portfolios with expansion and renewal responsibility.
  • Experience supporting workforce transformation, digital learning, or SaaS platforms.
  • Strong consultative skills and executive presence.
  • Ability to analyze data and translate insights into strategic recommendations.
  • Excellent communication, facilitation, and relationship-building skills.
  • Comfortable operating in a fast-growing, high-accountability environment.
  • Bonus: Experience with AI, digital transformation, L&D, or enterprise training platforms.

Compensation & Benefits

  • Competitive base salary with performance-based incentives.
  • Profit-sharing and long-term incentive opportunities.
  • Eligible for the company’s Phantom Stock Program, allowing participation in future company growth.
  • Comprehensive benefits package (health, dental, vision, Simple IRA, etc.).
  • Flexible work environment with a strong team culture.

How to Apply

Interested candidates should submit their resume and a cover letter. Apply here!