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Forward Deployed Engineer
Plain · San Francisco, California, USA
Pay
$180k–250k
Setting
Hybrid
Ship today's fix, build tomorrow's product
Listed by Plain for a position based in the United States. Employers on this board attest they are hiring domestically.
Solutions Engineer
Plain · San Francisco, California, USA
Pay
$175k–200k
Setting
On-site
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.
Listed by Plain for a position based in the United States. Employers on this board attest they are hiring domestically.
Product Marketing Lead
Plain · San Francisco, California, USA
Pay
$175k–215k
Setting
Hybrid
Plain is redefining customer support and customer success for the next generation of B2B companies. We’re building the fastest, most powerful platform to help companies move beyond reactive support and build meaningful customer relationships.
Some of the world’s most forward-thinking companies - like Cursor, Vercel, and Granola - trust Plain to unify all customer interactions, enable faster team collaboration, and supercharge their workflows with AI.
We have offices in SF and London. This role is hybrid with 3 days a week in our SF office. Because we work closely with our teammates in Europe, we start early, but you’ll find quiet afternoons for heads-down work.
WHY THIS ROLE IS SPECIAL
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 more technical, company-wide effort across Slack, Discord, and in-product experiences. Plain is leading the charge in building this new world, but redefining a category takes credibility and trust, not just features — and that's where you come in.
WHAT YOU’LL DO
We're hiring a Product Marketing Lead to help sales hit their number by ensuring that our positioning is clear and relevant for our target audience of customer experience leaders and engineers.
You will:
- Own positioning and messaging for our platform and suite of products, including how we differentiate and elevate customer value
- Craft proof points for our AI suite: give Ari and Sidekick each a clear market presence and real case studies with specific, provable outcomes
- Build the sales enablement system our AEs actually use: battlecards, competitive intel and the process to keep it current, a value-calculation asset, and a refined pitch deck and one-pagers
- Partner with Product as a two-way channel: own GTM strategy and execution for launches, and bring learnings from sales and the market back into the roadmap
- Conduct competitive and customer research that sharpens our value proposition, especially against other AI-in-support vendors
- Apply consistent messaging across the website, sales collateral, in-product experience, and every launch
THIS IS A GREAT FIT IF YOU…
- Have 5+ years of product marketing experience at a B2B startup focused on SMB and mid-market sales. Bonus points if you've previously sold to developers, other technical buyers, or customer support/CS functions.
- Have expertise crafting compelling messaging for mid-market customers and decision-makers
- Are a whiz at developing sales collateral with competitive positioning and objection handling
- Have exceptional organizational and project management skills — you can juggle multiple projects simultaneously
- Are entrepreneurial, with a high-ownership mindset — you thrive in fast-paced, high-growth environments
- Are an analytical, structured, logical thinker
- Have strong creative flair and design instinct — an intuition for what sits right, sounds and looks good
- Are highly driven and ambitious — you want to win
- Love an experimental approach and are happy to try new things
- Are comfortable working closely with senior leaders (CEO, CPO, Head of) and know how to hold your own point of view with them
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.
- Find learning about new technologies a key motivation for coming to work. We invest in what makes us productive but will prefer the known option to the experimental and novel. Postgres is great.
- Are looking to manage others. We're firmly looking for someone who, for now, wants to be an individual contributor.
- Expect all the perks of a big company. We’re a seed-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.
- Aren't excited about AI transforming customer experience (support & success)
- Aren't interested in working in person — this role is based in SF, and we work together in the office at least 3 days a week. You'll also likely visit customer offices, join in-person onboarding sessions, and build relationships face to face when it counts.
Listed by Plain for a position based in the United States. Employers on this board attest they are hiring domestically.
Support Engineer (SF)
Plain · San Francisco, California, USA
Pay
$150k–180k
Setting
Hybrid
As one of our Support Engineers, you'll be a clear owner of support during SF hours and a key member of a growing support function. You'll combine technical depth, strong judgment, and proactive communication to ensure customers, and the rest of the company, always feel support is under control.
Listed by Plain for a position based in the United States. Employers on this board attest they are hiring domestically.
Account Executive, High Velocity
Plain · San Francisco, California, USA
Pay
$220k
Setting
Hybrid
Own deals end-to-end and help build the revenue playbook from scratch
Listed by Plain for a position based in the United States. Employers on this board attest they are hiring domestically.
Partnerships Manager
Plain · San Francisco, California, USA
Pay
$140k–180k
Setting
Hybrid
Build Plain's partnerships function from the ground up
Listed by Plain for a position based in the United States. Employers on this board attest they are hiring domestically.
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