Account Executive

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 quieter 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

You’re joining a small but mighty GTM team - you'll be the first sales person in SF.

The US is where most of our customers are and you'll keep growing that market. That means more logos, more revenue, bringing more structure and repeatability to sales. All while helping us shape the product roadmap. This role is perfect for you if you obsess over sales and product and are looking to have a fundamental impact as part of a growing team.

We’re looking for someone who has at least 2-3 years of experience in sales at an early stage B2B SaaS company and loves helping customers fall in love with a product.

In this role, you will:

• You’ll be in charge of inbound leads, generating pipeline, and closing deals. You’ll own the deals that you lead end-to-end, including understanding customer pain points, helping them evaluate Plain, and negotiating final price and contract terms.

• You’ll work in collaboration with Cole in demand gen - he’s building the pipeline, we want you to close it.

• You’ll also continuously iterate sales fundamentals like ICP, pricing, segmentation, how we track deals, conversion ratios and how we build our TOFU/MOFU.

• Help us shape the product roadmap and be a sounding board to product engineering. We’ll rely on you to be the voice of our customers, using their feedback to shape our product decisions.

• You'll help onboard strategic customers with expansion potential alongside our Ops team, who will be your partner on the post-sale side.

This is a great fit if you…

• Have sold complex products that are integration heavy and highly customisable, like ours to SMB and mid market customers.

• Have seen sales motion in its infancy, ideally around the Seed - Series A or B stage.

• Are equally excited about crushing your quota as you are about building an outstanding product. We want to hear about the features and product improvements that have come from your customers’ feedback.

• Feel comfortable taking ownership in ambiguity. Our deals can move very quickly - we work very collaboratively but you should be excited to own deals independently and able to pull in the rest of the team as needed.

• You know how to talk about product in a way that energizes people, technical and non-technical. You love giving product demos, answering questions about roadmap, and coaching teams on how to use Plain as they’re evaluating, etc.

• You are exceptionally detail-oriented and good at time management - no action item or customer request gets lost. You’re able to coordinate communication async (mostly via Slack) and relay follow-up asks to the rest of the team to make sure we’re following up consistently.

• Love using a modern sales stack, including Linear, Attio, Clay, Notion, Slack, etc. We're building an industry disrupting tool, so we like to use other tools that are doing the same.

This won't be the right role if you…

• Are uncomfortable with ambiguity. We have some really exciting traction but are still at an early stage and are constantly learning and trying new things as our company grows.

• Are looking for a Head of Sales role. There is a ton of growth opportunity in a role like this, but right now we need someone who is excited by closing individual deals and helping us to keep up with our growing pipeline.

• Want to work within a larger sales team. Success in this role will be about being able to work independently, even as the company scales.

• Don’t enjoy working with product or engineering. Our sales process is very product-driven from start to finish.

• Expect all the perks of a big company. We’re a Series A stage startup and are competitive in what we offer at our stage, but it’s a different role and opportunity than working at an established tech company.

Note: We are an equal-opportunity employer. At this time, we can only support hiring within the US for this role.