Founding Sales Development Representative (SDR)

I'm Phil, Head of Sales at Plain, and the hiring manager for this role. You'll be the first SDR at Plain, which means you will help shape how we work and communicate with our customers. 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, tight-knit crew with offices in SF and London. This role is hybrid – 3 days a week in our SF office. We tend to start our days earlier (think 7:30/8 AM PT) so we get real-time overlap with our colleagues in Europe. WHY THIS ROLE IS SPECIAL We have strong inbound momentum and traction within the market and in order to get to the next level, we need someone who can take the signal we're seeing and turn it into conversations with the right people at the right companies. You'll work directly with the AEs and Head of Sales to build out what outbound looks like at Plain, everything from the sequences, the tooling, to the targeting logic, the messaging. This isn't an SDR role where you read from a script. It's a role where you obsess over the ICP, find creative ways in, and set up the kinds of meetings that actually convert. WHAT YOU'LL DO - Identify and prospect into our ICP primarily technical SaaS and AI companies (250+ employees) that are growing fast and have meaningful support complexity. - Build and run outbound sequences across email, LinkedIn, and phone. Experiment constantly with messaging, timing, and persona targeting. - Partner with AEs to ensure smooth handoff and use deal feedback to sharpen your approach upstream. - Work alongside Demand Gen to coordinate on market signals. You will monitor job postings, G2 reviews, product page visitors, and other intent triggers in order to turn them into personalized outreach. - Use modern tooling to build targeted prospect lists and personalize outreach. - Help define what "good" looks like: conversion benchmarks, messaging templates, and outreach cadences that become the foundation of our outbound motion. - Bring your learnings back to the team. what's resonating, what's not, and what we should do differently. THIS IS A GREAT FIT IF YOU… - Have 2+ years of SDR or BDR experience selling B2B SaaS, ideally into technical buyers (support, engineering, or ops personas). - Are obsessive about personalization, you don't send blasts, you send messages people feel were written specifically for them. - Are comfortable with AI tools like Claude Code and use them to move faster without losing quality. - Are energized by working in a space where the playbook doesn't exist yet and you see ambiguity as an opportunity to build something that matters. - Are curious about the product, the market, and the customers and you want to understand why Plain wins, not just when. - Want to be in office, building relationships with the AEs, and being sharp and plugged-in in the market. THIS WON'T BE THE RIGHT ROLE IF YOU… - Are uncomfortable with ambiguity. We have real traction but are still early, this role will require you to figure things out as you go, not follow a well-documented process. - Expect a high volume of warm leads handed to you. We're actively building the inbound engine, but outbound is yours to own. - Want to be fully remote or prefer to work independently without tight collaboration with AEs and GTM leadership. - Aren't excited by the details. Thoughtful, targeted outreach is table stakes here. spray-and-pray doesn't reflect how we think about customer relationships. - Need a defined career ladder before you join. There's a ton of growth opportunity here, including a path to AE, but right now we need someone who's motivated by building, not just advancing.