Founding Customer Success Leader

About Clearly AI

Clearly AI accelerates enterprise security and privacy reviews. Our platform helps users complete threat models, privacy impact reviews, and vendor risk evaluations in a fraction of the time. We are a seed-stage company of security and AI experts backed by strong investors including Y Combinator, Basis Set Ventures, and Argon Ventures.

You’ll be working closely with the founders and our rapidly-growing customer base, including leaders from Fortune 500s.

The Role

We’re hiring our first Customer Success Leader to ensure our customers achieve fast, measurable outcomes with Clearly AI and to lay the foundation for our CS function. This is a hands-on, high-impact role: you’ll partner with security, GRC and compliance leaders by optimizing their workflows and enabling them to adopt innovation more rapidly while building the processes, playbooks, and tools to maintain and grow customer relationships critical to our growth path.

If you’re excited about building momentum and being the voice of the customer inside a fast-moving YC-backed startup, we’d love to meet you.

What You’ll Do

• Own the post-sales journey: onboarding, training, adoption, renewals, and expansions
• Be a trusted advisor: guide CISOs, compliance, and security teams to achieve measurable ROI
• Build from scratch: create onboarding and success playbooks, customer resources, and health metrics
• Drive retention and growth: monitor account health, identify risks, and proactively manage renewals
• Shape our product: partner with Product/Engineering to bring customer insights directly into our roadmap
• Prepare for scale: establish key CS metrics and process, such as driving regular customer meetings, socializing future roadmap releases, and set the foundation for hiring as we expand
• Pre-sale POV support: take over the proof of value process and workflow, and integration mapping as Clearly proves organizational impact

What We’re Looking For

• 5-8+ years in Customer Success, Account Management, or Consulting in B2B SaaS
• Proven experience managing senior customer stakeholders (ideally CISO, CIO, CPO, or equivalent)
• A builder’s mindset: excited to create structure and process in an early-stage environment
• Exceptional communication skills, able to translate technical security/AI concepts into clear business value
• Startup DNA: adaptable, resourceful, and energized by ambiguity

Bonus Qualifications

• Background in security, compliance, or AI/ML-driven SaaS
• Experience with hands-on implementation and integrations (with products like ServiceNow, Jira, Google Drive)
• Experience with custom configurations and prompting based on customer needs

Why Join Clearly AI?

• Be the founding Customer Success hire getting to define and scale the CS function
• Work with security and privacy leaders at cutting-edge companies
• YC alum with proven, technical founders and strong growth momentum
• Competitive salary, equity, and benefits

Direct path to leadership opportunities as the company scales