Director of Customer Success, AI Academy

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Role: Director of Customer Success, AI Academy
Location: SmarterX HQ (Cleveland)
Reports To: General Manager, Chief Operating Officer (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 AllTM 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 90,000 contacts, and its flagship in-person conference, MAICON, draws 1,000+ 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 65,000+ 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 Director of Customer Success, AI Academy will be responsible for developing and executing strategies that enhance learner satisfaction, engagement, and long-term retention. This role will focus on optimizing onboarding, engagement, support, and renewal processes to drive customer success. 

The Director will work closely with marketing, sales, and product teams to align customer success efforts with AI Academy’s growth strategy.

Key Responsibilities

Customer Success Strategy & Execution

  • Develop and implement a customer success strategy that enhances learner experience and engagement.
  • Define key retention metrics and track progress against success goals.
  • Optimize learner onboarding, engagement, and renewal processes to increase satisfaction and loyalty.
  • Support AI agent planning, development, management and integration for customer success operations.

Onboarding & Engagement

  • Design and execute onboarding programs that ensure new learners achieve early success.
  • Develop engagement initiatives, including community interactions, learning challenges, and peer collaboration.
  • Work with marketing to create content and resources that enhance engagement and learning outcomes.

Member Communications

  • Develop and execute a member communication strategy to drive utilization, course completion rates, retention, growth, and Net Promoter Score (NPS).
  • Craft onboarding communications to ensure new members quickly understand and engage with AI Academy resources.
  • Develop and manage email nurturing sequences to guide members through their learning journey, encourage course completion, and highlight additional opportunities.
  • Implement AI-driven personalization to tailor messaging based on member behavior, progress, and interests.
  • Monitor engagement metrics and continuously refine communications to maximize impact and retention.
  • Collaborate with product and marketing teams to align messaging with business goals and member needs.

Customer Support & Relationship Management

  • Oversee customer support processes, ensuring prompt and effective resolution of learner inquiries.
  • Build strong relationships with learners to gather feedback and improve program offerings.
  • Implement proactive support strategies, reducing churn and increasing customer lifetime value.

AI Academy Membership Retention & Expansion

  • Develop strategies to increase membership renewals and upsell opportunities.
  • Collaborate with sales and marketing to identify expansion opportunities within existing learners.
  • Leverage data insights to refine success programs and improve overall learner outcomes.

Cross-Functional Collaboration

  • Work closely with Marketing, Sales, and Product teams to align customer success efforts with broader business objectives.
  • Provide feedback to course development teams to ensure learning experiences meet customer needs.
  • Support AI Academy’s integration with SmarterX and Marketing AI Institute initiatives.

AI Agent Management

  • Oversee and optimize AI-powered customer success agents to enhance member engagement, support, and retention.
  • Ensure AI agents are trained with up-to-date knowledge of AI Academy offerings, helping members navigate courses, certifications, and resources.
  • Leverage AI-driven automation for personalized onboarding, proactive check-ins, and member success recommendations.
  • Monitor AI agent interactions, refine responses, and improve workflows to increase efficiency, satisfaction, and Net Promoter Score (NPS).
  • Continuously evaluate and implement AI-driven strategies to improve the overall customer success experience.

Qualifications & Experience

  • Proven experience in customer success, learner engagement, or client relationship management roles.
  • Experience managing customer onboarding, retention strategies, and engagement programs.
  • Strong background in education, online learning, or membership-based services.
  • Ability to analyze customer data and insights to drive decision-making and improvements.
  • Strong leadership, communication, and relationship-building skills.
  • Experience working with CRM, customer support platforms, and engagement tools.
  • Deep experience with HubSpot is preferred.
  • Advanced prompting abilities with standard LLMs and reasoning models. 
  • Extensive experience with OpenAI ChatGPT, Anthropic Claude, Google Gemini and / or Microsoft Copilot.

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 outlining their experience and vision for customer success at the AI Academy at SmarterX. Apply here!