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 Cursor, Raycast, and Sanity - trust Plain to unify all customer interactions, enable faster team collaboration, and supercharge their workflows with AI.

We’re a tight-knit team with offices in SF and London. This role is based in San Francisco with an expectation of 3 days a week in person. Because we work closely with our teammates in Europe, we start early (around 7am PT) - you’ll find quiet afternoons for heads-down work (and plenty of coffee in the morning).

Why this role matters

We’ve just had our biggest quarter yet, closing deals with some of the fastest-growing technology companies. The US is our largest market, and we’re expanding our GTM team to capture that momentum.

You’ll be one of the first AEs on the ground in SF, reporting directly to our CEO. You’ll have a front-row seat in shaping both our revenue engine and our product roadmap, while building deep relationships with some of the most exciting tech companies out there.

This role is for someone who:

• Obsessively hunts new business, but also cares deeply about product.
• Thrives in ambiguity and sees “lack of playbook” as an opportunity to write one.
• Wants their fingerprints all over the growth story of a Series A company.

What you’ll do

• Own 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.
• Work in collaboration with Cole in demand gen - he’s building the pipeline, we want you to close it.
• Continuously iterate sales fundamentals like ICP, pricing, segmentation, how we track deals, conversion ratios and how we build our TOFU/MOFU.
• Bring the voice of the customer into product decisions; be a trusted partner to product and engineering.
• 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…

• You’ve sold complex, integration-heavy B2B SaaS to SMB or mid-market customers. Bonus: the more technical the better.
• You’ve been part of an early GTM team (Series A to Series B) and know what “building from scratch” looks like.
• You love the craft of sales - running crisp discovery, delivering the best product demos, and negotiating with confidence.
• You’re detail-oriented and thrive in a fast-moving environment where no two deals look exactly the same.
• You care as much about shaping product as you do about hitting quota.
• You want to be in office, and being in-market in San Francisco, meeting customers and learning from peers.

This won’t be the right fit 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 where there’s layers of SDRs and SEs supporting you. You’ll be hands-on across the full cycle.
• 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.