Strategic 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 🎵.

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.
• Manage and grow key accounts from onboarding onwards: Build deep relationships with our most important customers. Track health, drive renewals, and identify expansion opportunities.
• Be hyper-communicative: Set expectations early and often with customers around high-velocity, high-volume communication.
• Be the voice of the customer: Advocate for customer priorities internally, influence product roadmap conversations.
• Collaborate deeply with sales and product: Work with sales on handoffs and expansion conversations.

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 and get energy from helping customers ramp quickly.
• Are an exceptional communicator who defaults to over-communicating.
• Can juggle competing feature requests from multiple customers.
• Have great product sense and understand trade-offs.
• Want to work closely with sales and product, not in a silo.
• 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.
• See yourself as purely an Account Manager.
• Prefer working behind the scenes.
• Need cleanly drawn lines of ownership between sales and product.
• Don't enjoy fast-paced, proactive communication.
• Want a management position right away.
• Need everything figured out.

Compensation Range: $180K - $215K