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VP of Customer Success | AI SaaS - ($240k + equity)

100% remote Flexible hours Hiring now

About the company The company is the #1 enablement AI. We help enterprises create training using AI and push it right to reps via SMS, Slack, and Teams chat. The result: reps remember 9x more and Enablement teams launch critical trainings 20x faster. We are looking for a VP of Customer Success with 15+ years of experience to lead our CS function through a pivotal product transformation. The ideal candidate is an entrepreneurial and sales-minded leader who can build a new customer success motion from the ground up for our cutting-edge AI agents. You will be instrumental in transitioning our Fortune 500 customers to our new agent-first model and scaling the team for future growth. We need a creative, hands-on leader who is not tied to outdated SaaS playbooks and can thrive in a fast-paced, evolving environment. What will you be doing?

  • Lead and scale the customer success team, taking over a team of six and hiring for technical implementation roles.
  • Develop and execute a new, agent-first customer success motion for our AI-powered platform, moving beyond traditional SaaS playbooks.
  • Partner directly with enterprise customers to consult on technical implementation, data models, and the adoption of AI agents within their organizations.
  • Collaborate closely with the product and engineering teams to influence the product roadmap and lead the deployment of new agents with design partners.
  • Drive account growth and retention by creating strategic account plans, coaching CSMs, and identifying and mitigating risks across our book of business.

Requirements:

  • Must have worked at a startup

or high- growth tech company.

  • 5+ years in a CS leadership or management role, ideally as an IC at a startup before stepping into leadership
  • Built a customer success motion from the ground up.
  • Experience deploying technology into Fortune 500 companies.

Hard skills

  • Demonstrated a consultative, sales- oriented approach

to CS.

  • Experience influencing a technical product's roadmap.

Soft skills

  • Entrepreneurial mindset comfortable with ambiguity and building from scratch.
  • Creative and proactive problem- solver ('artist not a scientist').

Why candidates should join

  • The company is the #1 enablement AI that helps enterprises create training using AI and push it right to reps via SMS, Slack, and Teams. They've 3x'd revenue in the past year and work with 34+ Fortune 500 customers.
  • You'll work directly with co-founder to build the CS function from scratch at a Series A startup with $16M funding from top investors like PeakSpan Capital. This isn't spreadsheet management - you'll get into the weeds with accounts and lead cutting-edge agentic transformations.
  • VP of Customer Success role managing 6 team members with $200-240k base plus equity and uncapped commission potential. You'll pioneer new CS approaches for AI agents while working with enterprise clients in regulated sectors like Life Sciences and Manufacturing.

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