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 true customer relationships.

B2B customer support is undergoing a seismic shift. AI is transforming the way companies engage with customers, shifting support from a siloed function to a company-wide effort across Slack, Discord, and in-product experiences. The old way - slow, manual, and disconnected - no longer works.

Some of the world’s most forward-thinking companies - like Stytch, Sanity, and Fly.io - trust Plain to unify all customer interactions, enable faster team collaboration, and supercharge their workflows with AI.

We’re a small team and have offices in SF and London. This role is based in our SF office with an expectation of 3+ days/week in person.

We do ask for availability starting around 7am PT to sync with our teammates in Europe — yes, it’s early, and yes, we’ll have coffee ready. The bright side is your afternoons are usually quiet and perfect for heads-down, focused work. We totally get that this schedule isn’t ideal for everyone, so we want to be upfront about it from the start.

What you'll do

As our first dedicated Customer Success Manager, you’ll play a foundational role in helping our customers get the most out of Plain - from onboarding through renewal.

This is a hybrid role that spans onboarding, post-sales success, support enablement, and product feedback. You’ll work closely with customers, product engineering, support, and sales to ensure our customers are successful and excited to grow with us.

What makes this role special you ask? You won’t just be supporting customers, you’ll be doing that 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 who has at least 3 years of experience working in a CS or post-sales role at an early stage B2B SaaS company and loves helping customers fall in love with our product.

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

• Own customer onboarding: including gathering context from sales, leading customer onboardings, and building relationships with high-value customers early on to drive adoption and long-term success.
• Own renewals and expansions: Track contract timelines, uncover new use cases, and drive upsell conversations in partnership with product and sales.
• Be the voice of the customer: Gather and summarise feedback, advocate for customer priorities, and influence product roadmap conversations.
• Improve customer education: Help improve onboarding flows, support docs, and async resources so customers can self-serve with confidence.
• Stay close to support: Work closely with the support team to triage escalations, follow up on feedback, and evolve how we support our users with Plain itself.

This is a great fit if you…

• Have 3–5 years’ experience in a Customer Success, CX, or post-sales role at an early-stage B2B SaaS company.
• Are hands-on and proactive - you’re quick to jump into Slack or on a call with a customer, work with multiple stakeholders, various asks and follow up consistently.
• Have great product sense - you can translate feedback into structured insights and know how to push back constructively.
• Communicate clearly and thoughtfully - you know when to go async and when to hop on a video call.
• Have supported $10k-50k+ ACV customers and can manage multiple accounts without dropping the ball.
• Enjoy working cross-functionally with product, GTM, and support - you’ll be in the middle of everything and should love this.
• Are excited to help build the foundations of customer success at Plain from scratch.
• 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…

Prefer working behind the scenes - this is a high-touch, customer-facing role.

• Don’t enjoy fast-paced and proactive communication - most conversations happen in calls, as well as Slack and Notion
• 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.
• Aren’t interested in working in person - this role is based in SF, and we work together in the office at least 3 days a week. You’ll also likely visit customer offices, join in-person onboarding sessions, and build relationships face-to-face when it counts.