Founding Customer Success Manager; Enterprise CSM

Founding Customer Success Manager (Enterprise) — Othello.ai

📍 SF and NYC (In office, either location)

💼 Full-time | Early-stage, high-ownership role. Comp: $80K-$120K

Othello.ai is redefining how enterprise sales teams execute in live customer conversations. Othello is a real-time sales coach that can give suggestions to reps during video and phone calls. We fix the core gap in sales leadership – leaders provide reps with strategies, playbooks, and tools to improve, but reps fail to apply those strategies in real conversations.

Our customers range from Fortune 500 enterprises to fast-growing scale-ups. Pipeline has grown 5x and then 10x over the last two months, creating an immediate need for a dedicated customer success expert.

We’re building the category, and we’re looking for a Founding Customer Success Manager to help us do it.

To make this clear: it is highly likely that you will need to work 12-hour days every weekday for months on end. To make this clear – only apply for this job if you are comfortable with it.

This is not a traditional “support” CS role. As a founding hire, you’ll own enterprise customer relationships end-to-end and play a critical role in shaping our customer success motion, feedback loops, and product roadmap.

• 5–10 years of Enterprise Customer Success experience, ideally in B2B SaaS
• 3 year of experience as a CS rep at a startup.
• Background working with technical products (e.g., sales tech, data platforms, AI, analytics, infrastructure, or similarly complex software)
• Comfortable engaging with and influencing senior stakeholders (VP , C-level)

• Own and manage relationships with enterprise customers from post-sale onboarding through long-term expansion and renewal
• Lead executive-level success reviews, value storytelling, and ROI conversations
  
  Partner closely with our CEO, CTO, product team, and sales team:
• Translate customer feedback into product direction
• Refine onboarding, success frameworks, and playbooks
• Identify expansion and upsell opportunities
• Help design and scale Othello.ai’s customer success processes from the ground up

This role will be incredibly rewarding for the right person—but it’s not for everyone.

This is not a good fit if you:

• Prefer a highly structured, fully built-out Customer Success org with established playbooks, tooling, and handoffs
• Are looking for a narrow, reactive CS role focused primarily on ticketing, support, or order-taking
• Are uncomfortable working directly with senior enterprise stakeholders (VP , C-level) and leading strategic conversations

This role is for someone who wants to help define how Customer Success is done —and is energized by shaping both the customer experience and the company itself.

If you’re excited about working closely with enterprise customers, shaping how Customer Success is done at an early‑stage company, and building something genuinely new—we’d love to talk.

👉 Apply here or DM us to start the conversation.