Customer Success Manager

Plain is redefining customer support for the next generation of B2B companies. We're building the fastest, most powerful platform to help companies move beyond reactive support and build real customer relationships. Some of the world's most forward-thinking companies — including Cursor, Ashby, Vercel, and Granola — use Plain to unify customer interactions, collaborate faster, and supercharge their workflows with AI.

This role is hybrid (3 days in-office) from our San Francisco office. We tend to start our work days earlier to overlap with our EU colleagues (7:30-8am), but we promise to provide the coffee/tea ☕ and morning tunes.

What you'll do:

• You'll be joining our Customer Success team to own onboarding and account management for our top-tier customers. Your focus is making sure these customers get to value fast, stay deeply engaged with Plain, and have a world-class experience throughout.
• This is a hybrid role that spans onboarding, account management, product feedback, and cross-functional collaboration. You'll work hand-in-hand with sales, product & engineering, and support.
• What makes this role special? You won't just be supporting customers, you'll be doing it through Plain itself. Our product is designed to power high-quality customer interactions and you'll be using it every day. The feedback you gather and the insights you surface will directly shape how we build the product, both for you and our customers.

We're looking for someone with 5+ years of experience in a CS or post-sales role at an early-stage B2B SaaS company who is obsessed with helping customers succeed.

Here's what the role looks like day-to-day:

• Own onboarding for top customers: Gather context from sales, lead onboarding end-to-end, and drive customers to value as quickly as possible. You'll set the pace, remove blockers, and make sure every customer understands how to tie Plain to their success metrics and business cases from day one.
• Manage and grow key accounts from onboarding onwards: Build deep relationships with our most important customers. Track health, drive renewals, and identify expansion opportunities by staying close to what they need and where they're headed.
• Be hyper-communicative: Set expectations early and often with customers around high-velocity, high-volume communication. You're the kind of person who over-communicates on timelines, proactively shares updates, and keeps customers in the loop even when there's nothing new.
• Be the voice of the customer: Advocate for customer priorities internally, influence product roadmap conversations, and make sure the team always has clear visibility into what our top customers need. You’re able to distill customer requests into actionable, scoped requests for product & engineering or push back thoughtfully when a request isn't the right fit.
• Collaborate deeply with sales and product: Work with sales on handoffs and expansion conversations. Partner with product engineering to share insights, validate solutions, and close the loop with customers when their feedback ships.

This is a great fit if you…

• Have 5+ years' experience in a Customer Success or post-sales role at an early-stage B2B SaaS company.
• Know what it takes to manage high-value accounts without dropping the ball.
• Love the onboarding phase. You get energy from helping customers ramp quickly, defining success criteria, and tying product adoption to real business outcomes.
• Are an exceptional communicator who defaults to over-communicating. You're comfortable setting the tone for high-velocity interactions with customers and thrive in that rhythm.
• Can juggle competing feature requests from multiple customers and turn messy feedback into structured, scoped asks that product and engineering can act on. You know when to advocate and when to push back.
• Have great product sense. You understand trade-offs, can speak credibly about roadmap priorities, and are constructive when the answer is 'not right now.'
• Want to work closely with sales and product, not in a silo. You see yourself as a connector across these teams, not a handoff point.
• Are excited to help build the foundations of customer success at Plain.
• BONUS: Can handle technical topics with ease — while this isn't an engineering role, you'll be comfortable talking APIs, webhooks, integrations, and workflows with customers.

This won't be the right role if you…

• Can’t handle competing priorities across multiple accounts. Our top customers move fast and you should be up for the challenge of keeping up!
• See yourself as purely an Account Manager. This role requires getting into the nitty-gritty of onboarding, troubleshooting, and deeply understanding how customers use Plain, not just managing relationships.
• Prefer working behind the scenes - this is a high-touch, customer-facing role where you'll spend most of your day in direct conversation with customers.
• Need cleanly drawn lines of ownership between sales and product. You'll be working tightly with both teams and should be excited about that overlap, not uncomfortable with it.
• Don't enjoy fast-paced, proactive communication. Most conversations happen on calls, in Slack, and in Notion, and the pace is high.
• Want a management position right away, this is an individual contributor role.
• Need everything figured out - we're a small team, and ambiguity is part of the job.

Compensation Range: $180K - $215K