Join an intentionally small team as our second CS hire to define the post-sales playbook for high-growth technical teams like Cursor and Raycast. You will act as "customer zero," using our beautifully designed platform daily to support customers, while directly influencing the product roadmap through a tight feedback loop with engineering.
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Customer Success Manager at Plain
Are you a product-driven CS leader looking to join an elite team backed by Index and Battery Ventures? We are building the support platform technical teams actually love—used by industry leaders like Cursor and Raycast. As our second Customer Success Manager, you'll be 'customer zero,' using our own speed-optimized tool to manage high-value accounts while directly shaping the product roadmap. If you have 2-3 years of experience at a high-quality SaaS startup and want to build a CS function from the ground up in San Francisco, this $130k-$160k role with meaningful equity is for you.
About this role
Role overview
About the company
Software30-50 employees
Plain is a collaborative B2B customer support platform. We’ve raised over $24 million from some of the world’s best investors: Index Ventures and Battery Ventures. We power support for 100's of high-growth companies like Vercel, Cursor, Granola, Raycast, n8n and many more. We do this by being more flexible and extensible than anyone else. With Plain, customers can build any workflow, tool, UI and data model they can dream of - no-code or all-code.
What you'll do
What you will do
- Own the end-to-end onboarding and relationship management for high-value accounts to drive long-term adoption and technical success.
- Manage the full renewal and expansion lifecycle, identifying new use cases and driving upsell opportunities in partnership with sales.
- Create and scale customer education resources, including onboarding flows and support documentation, to empower users to self-serve.
Who you are
Who this is a fit for
- 2-3 years of customer success or post-sales experience at an early-stage B2B SaaS company known for product excellence.
- Strong product intuition with the ability to translate complex customer feedback into actionable insights for engineering and design teams.
- Comfortable in a fast-paced environment with a 7-8 AM start to support a global customer base across multiple time zones.
Why this role
Why this role is remarkable
- Act as "customer zero" by using the product daily to support users, giving you unique leverage to shape design and engineering priorities.
- Work alongside a world-class team from product-led giants like Superhuman, Coda, and Grammarly in a high-impact, intentionally lean environment.
- Enjoy a hybrid SF lifestyle with incredible perks including $1k home setup, 35+ days of vacation, and quarterly global off-sites.
Jack & Jill
How Jack & Jill work together
I get to know what you’re great at, then find roles you’d never find yourself.Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.
I recruit from Jack’s network and make the intro when I spot a great match.And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.
Meet Jack
Jack gets to know what you're great at and what you want next, then searches 15 million jobs daily and helps you discover roles at companies like this.
How does this work?
Jack’s an AI agent for job searching and career coaching. He works for you.
Jill is the AI recruiter working for the company. She recruits from Jack’s network.
If it’s a match and the company wants to meet you, they’ll make the intro. In the meantime, if you’d like, Jack will send you excellent alternatives.