About the role
I'm Phil , Head of Sales at Plain, and the hiring manager for this role. 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. Some of the world's most forward-thinking companies, like Cursor, Ashby, and Sanity, trust Plain to unify all customer interactions, enable faster team collaboration, and supercharge their workflows with AI. We're a small team with offices in SF and London. This role is hybrid with 3 days a week in our SF office. Why this role is special You’ll be one of the first AEs on the ground in SF. 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.
What you'll do Own inbound leads, generate pipeline, and close deals. You’ll own the deals from end-to-end, including understanding customer pain points, helping them evaluate Plain, and negotiating final price and contract terms. Work in collaboration with Demand Gen - they are 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 customers with expansion potential alongside our Ops team, who will be your partner on the post-sale side. You will be joining our Velocity segment which sells to companies that are from 5-249 employees. This is a great fit if you… Have sold complex, integration-heavy B2B SaaS to SMB.
Bonus: the more technical the better. Been part of an early GTM team (Series A to Series B) and know what “building from scratch” looks like. Love the craft of sales - running crisp discovery, delivering the best product demos, and negotiating with confidence. Are detail-oriented and thrive in a fast-moving environment where no two deals look exactly the same. Care as much about shaping product as you do about hitting quota. Want to be in office, and being in-market in San Francisco, meeting customers and learning from peers. 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 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
