Solutions Engineer: Lead Technical Evaluations & POCs

Plain; San Francisco (CA); On-site; Full time

Job description

I'm Phil, Head of Sales at Plain, and the hiring manager for this role. You'd be joining as a partner to the sales team while working closely with our Engineering team to become the technical driver of our most important deals.

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 are at a genuinely interesting inflection point. Companies are rethinking what support infrastructure should look like in an AI-native world, and we're building the answer. Our customers are some of the most technically sophisticated teams out there, and that makes the work interesting.

You'll have real ownership, a short path to product and engineering, and the chance to build this function from the ground up.

Plain is leading the charge in building this new world, as our Solutions Engineer, you'll own the technical side of every strategic deal. You'll sit alongside our Account Executives and CSM’s to help pre and post sale demonstrate the value of Plain through the entire customer lifecycle, from discovery call to customer deployment. You will have a critical role guiding technical evaluations, and leading POCs that prove Plain can do exactly what we say it can.

You'll also be a direct line between prospects and our product team. The patterns you spot in evaluations, the questions that keep coming up, the features that close or lose deals, etc. All of these signals will shape what we build next.

What you'll do

• Drive the technical evaluation. You will be part of building this function from the ground up. You will establish how the SE team will partner with Account Executives and CSMs and be the bridge between pre-sale and post-sale onboarding. Be the primary technical contact from discovery onwards, throughout the sales cycle. You will be co-selling with the sales team to help push deals through an effective evaluation.

• Lead Technical Evaluation of POCs. Help guide the pre-sale motion by connecting a prospects environment with Plain to create a strong evaluation of how they will use Plain to solve their problems. Manage everything from, troubleshooting blockers and connections, in order to make sure their team walks away confident Plain is the right call.

• Go deep on the product. Be an expert on all things Plain. Be able to show and highlight how the product can work and how to make it work in unique environments. You'll be guiding customers through complex use cases and you need to have been there yourself.

• Influence the roadmap. Feed structured signal back to product and engineering. If something comes up in every evaluation, we need to know. You're the voice of the technical buyer.

This is a great fit if you…

• Have 4+ years in solutions engineering, sales engineering, or technical pre-sales at a SaaS company, ideally one with a developer audience or complex technical product.

• Want to have your hands in both pre- and post- sales and help the customer throughout their entire evaluation and onboarding journey.

• Are a builder at heart: you can educate a technical buyer on how Plain works in real time, and are equally excited to help them customize Plain to their own workflows.

• You’re scrappy and creative: You want to fully understand and solve a prospect’s pain points or understand their product feedback before sharing with engineering.

• Communicate concisely and effectively. You are able to explain something complex to both technical and non-technical buyers.

• Are excited by working somewhere small where your work is visible and your impact is real.

• Are technically strong: understand APIs, you can read logs, write SQL, webhooks, and how systems work under the hood.

This won't be the right role if you…

• Want a large, structured SE org with defined playbooks, clear territories, and a team to hand off to.

• Prefer to stay in the background, this is a high-visibility role, internally and externally.

• Aren't interested in getting technical. "I'll loop in engineering" won't cut it here.

• Need everything figured out before you can operate confidently. There are no playbooks here yet - this is an opportunity to build them yourself.

• Aren't energized by the idea of being the first person in this function at a company that's still being built.