Vice President of Customer Success, AI Academy

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Role: Vice President of Customer Success, AI Academy
Location: SmarterX HQ (Cleveland)
Reports To: General Manager, AI Academy / 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 Vice President of Customer Success, AI Academy is the senior leader responsible for the end-to-end customer experience for all AI Academy customers, including individual learners, Standard Business Accounts (5-99 licenses), and Premium / Enterprise Business Accounts (100+ licenses and high-growth potential).

The VP of Customer Success is charged with building an industry-leading, AI-forward department that drives customer transformation and can scale to 250,000+ licenses in the next 3-5 years.

Key Responsibilities

Customer Success Strategy & Ownership

  • Own the customer experience lifecycle from onboarding through renewal across all AI Academy customer types.

  • Design and evolve a tiered CS model that delivers outcomes efficiently at scale.

  • Align Customer Success strategy directly to license growth and ARR expansion.

  • Serve as the executive owner of customer outcomes within the AI Academy leadership team.

Team Leadership & Structure

  • Lead and develop leaders and teams across:
    • Customer Success Managers (Premium / Enterprise Accounts)
    • Customer Success Managers (Standard Accounts)
    • Customer Support Managers and Specialists
  • Define capacity models, coverage ratios, and service levels by customer tier.
  • Build scalable hiring, onboarding, enablement, and career paths for CS roles.

Adoption, Retention & Expansion

  • Ensure strong onboarding, adoption, and value realization across Individuals and Business Accounts.
  • Oversee renewal readiness and expansion motions in partnership with Sales.
  • Establish playbooks for proactive engagement based on usage, health, and growth signals.
  • Drive continuous improvement in license utilization and customer lifetime value.

Customer Support Leadership

  • Own the performance of the pooled Customer Support function (human + AI).
  • Ensure fast, accurate, and high-quality support across email, chat, and self-serve channels.
  • Optimize support workflows to balance efficiency, accuracy, and customer satisfaction.

Customer 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 journeys, encourage course completions, 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.

AI & Automation Enablement

  • Own the strategy and performance of AI agents supporting onboarding, support, reporting, and communications.
  • Ensure AI agents are accurate, well-trained, and continuously improved.
  • Use AI to scale Customer Success without sacrificing quality or outcomes.

Data, Insights & Operations

  • Define and manage CS dashboards and reporting tied to licenses, utilization, and ARR.
  • Monitor customer health through adoption, engagement, and utilization metrics.
  • Turn data into insights and insights into action across CS and Support teams.
  • Partner with Ops and Product to optimize CS tooling (CRM, LMS analytics, support platforms).

Cross-Functional Leadership

  • Partner closely with:
    • Sales on renewals, expansions, and account strategy.
    • Learning on curriculum effectiveness and outcomes.
    • Marketing on lifecycle communications and retention initiatives.
    • Operations on staffing models and scalability.
  • Ensure clean handoffs and alignment across the customer journey.

AI Agent Management

  • Own roadmap and performance of customer-facing AI agents.
  • Ensure agents support both Individual and Business customers effectively.
  • Continuously refine AI-powered workflows to improve efficiency and experience.

Qualifications & Experience

  • 10+ years in Customer Success, Account Management, or related leadership roles.
  • Proven experience owning license-based and ARR-driven customer models.
  • Experience leading multi-tier CS organizations (self-serve, scaled, enterprise).
  • Strong executive presence and experience working with senior stakeholders.
  • Deep comfort with data-driven decision-making and CS metrics.
  • Experience scaling teams and systems in high-growth environments.
  • Bonus: Experience leading teams for education platforms, SaaS businesses, or consulting firms.

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!