Founding Engineer at Tightknit AI – Remote (Canada) | Jobyssey

Overview

Hi 👋 I’m Stephen, Co-Founder and CTO at Tightknit. We are on a mission to revolutionize online communities with an innovative platform built for trust, engagement, and connection, especially meeting members where they are within an app they already love: Slack. Tightknit powers customer and developer communities for teams like Clay, MotherDuck, Mixpanel, Vanta, Gamma, and Stripe.

Our vision is to make communities a bastion of genuine human relationship and the OS for every business’s sales & marketing team. And we are hiring our first Founding Engineer to help us build that future!

As an early engineer, you will:

Work directly with the CTO
Define architecture, not just implement it
Shape product direction, not just execute it
Own systems end-to-end (design → implementation → monitoring → iteration)
Interact directly with customers
Build internal AI workflows to accelerate our velocity
Help determine how engineering operates here
Wear many hats and operate independently with high accountability

This isn’t just a coding role. It is a seat at the table. In fact, while programming knowledge matters, in the AI age it’s becoming less and less central to our day-to-day work. So who are we really looking for?

Engineer with taste - Put away the IDE for a moment and put on your PM hat. We trust in your ability to talk to customers, synthesize their asks, and create excellent products with extreme level of thoughtfulness and detail. You hold yourself and your work to a high bar.
Engineer who can design - You don’t need to be a front-end wizard (although we’d love if you are!), but you have a good eye for distinguishing good vs. bad UX. Don’t expect sloppiness in any area of the stack to be fixed by someone else.
Engineer who can manage - Everyone now has access to an army of digital employees and the best programmers on earth. Can you effectively use them to multiply yourself and our team? Oh and did we mention, everyone at Tightknit is a community manager! 🙌

What We're Looking For

This is a staff-level role, so we require at least 5+ years of experience as a full-time full-stack engineer. You must possess strong backend engineering fundamentals and experience designing production systems.

Experience at an early-stage startup or working directly with founders is strongly preferred. Experience delivering enterprise products is a bonus.

Smarter, Better, Faster, Stronger

We believe every hire either makes us “smarter” (fills in our weak spots) or “stronger” (adds fuel to our strengths), or both! For this role, we will be honing in especially on candidates whose skills make us smarter.

Here’s a fun visual of where we think our team’s strengths / preferences currently lie:

Front-End  🟪🟪🟪🟪🟪 / 🟦🟦🟦🟦⬜
Back-End   🟪🟪🟪⬜⬜ / 🟦🟦🟦🟦🟦
Infra/Ops  🟪🟪🟪⬜⬜ / 🟦🟦🟦🟦⬜
API        🟪🟪🟪🟪⬜ / 🟦🟦🟦🟦⬜
Perf       🟪🟪🟪⬜⬜ / 🟦🟦🟦🟦⬜
Security   🟪🟪🟪🟪⬜ / 🟦🟦🟦🟦⬜
Database   🟪🟪⬜⬜⬜ / 🟦🟦🟦🟦🟦
Humility   🟪🟪🟪🟪⬜ / 🟦🟦🟦🟦⬜
             ^us          ^you??

Technology Stack

You do not need to know all of these perfectly on day one, but you must be able to learn quickly.

Languages & Frameworks: Javascript / Typescript, React, Next.js, TanStack, Node.js, Tailwind
Infrastructure & Cloud: Cloudflare ecosystem (Workers, KV, Durable Objects, Workflows, Queues), Vercel
Data: PostgresSQL, Drizzle, Supabase
Platforms: Slack platform, OpenAPI APIs, and event-driven architectures
Tools: Github, Linear, Slack, OpenAI, Claude, Cursor, Antigravity, Notion, Posthog, Mintlify, Canva, Sentry (suggest something to us!)

Interview Process

Intro Call (30 minutes) - get to know each other, brag about how many LLM tokens you use, we demo Tightknit, etc.
Technical Screen (1 hour)
Open-Ended Technical Exercise (2 hours) - pair programming simulation, open-ended exercises
Founders Call(s) (30 minutes) - hear our vision, make sure you like us and we like you and you are not a sociopath thank you! 🤍
Reach out to References - we may ask you for references, so others may also confirm you are indeed not a sociopath

Compatibility Check

SuperDay (typically 1 day) - paid work trial, designed as a mutual compatibility check so you can see what it’s like to work with us (and we can learn what it’s like to work with you). This is a pragmatic test of fit that ensures everyone is genuinely excited about the partnership. It is not designed as a technical test.

SuperDay

The final stage of our process is what we call a SuperDay. This is typically one paid full day of work with us, which we can flexibly arrange around the candidate's schedule. The goal is a mutual compatibility check so all of us can get a real sense of what it’d be like to work together. The SuperDay may be done remotely or in person if nearby one of our co-working spaces. We are not able to bypass this stage so if the candidate is not interested in doing this final step, unfortunately we will have to part ways and the candidate will no longer be considered for the role.

💡We can be very flexible with scheduling! For example, we can split the SuperDay into half-days, do it in the evenings, or schedule it on a weekend as needed.

The candidate will be working on mock tasks similar to the real-world day-to-day work someone in this role does at Tightknit. They will also have the chance to meet a few of their potential direct team members, and if they haven’t already, our founders. This gives the candidate a chance to show off their skills, and for us to see the quality, speed and communication of the candidate. Overall, the candidate should aim to spend at least 80% of their time and energy on the task and less than 20% on meeting people, as we will base our decision primarily on the output of the day.

We pay all candidates a flat rate of $500 USD for their SuperDay efforts. On rare occasions, if we have to cancel a scheduled SuperDay arrangement because we have filled the role with another candidate who was further advanced in the process, we will pay a $250 USD term fee to the candidate for their efforts up until that point. If the candidate is unable to accept payment for the SuperDay, we will donate the amount to an agreed upon charity of their choice.

As a part of the SuperDay arrangement, you will be asked to sign an NDA / CLA and may be provided with a mocked and/or siloed codebase.

Your First Two Months at Tightknit

Week 1–2

Complete your SuperDay.
Join the Slack customer community and see how real users think.
Form strong opinions about our architecture, product gaps, and velocity constraints.
Release a small to medium-sized feature. Improve something meaningful.
Ship production code.

Weeks 3–4

Own a scoped but consequential project end-to-end.
Propose improvements to our systems (engineering, AI workflows, APIs, performance, etc.).
Start shaping how engineering should operate here — not just participating in it.

Month 2

Lead a cross-cutting initiative (integration, refactor, reliability improvement, new surface area).
Have direct customer conversations.
Make at least one architectural decision that meaningfully improves our trajectory.

By the end of two months, success looks like this:

You’ve taken full ownership of at least one initiative.
You’ve earned trust through action and follow-through.
You’ve helped us move faster without lowering our standards.
You’re clearly operating as a founder-level multiplier — not waiting to be told what to do, but defining what should exist next.
You wake up excited to come work alongside this team!

What you might work on

Our integrations platform which connects into numerous different applications where customer engagement can happen
Our embedding & retrieval architecture, powering our intelligence layer and unified semantic and keyword search
Our AI agent for community programming

Benefits

Competitive salary and equity.
10-year exercise window for stock options. You shouldn’t feel pressure to purchase stock options if you leave Tightknit. Do it when you feel financially comfortable.
Unlimited PTO, and we will encourage you to take it.
A minimum of 8 weeks of fully paid parental leave.
Generous budget for equipment, software, and ergonomics. Get what you need to be happy and productive!
$100/month community membership and education budget, with more expensive items (like conferences) covered with manager approval.
Membership to a co-working space if you are located in SF or NYC.
If you’re in the US, we offer top-tier health insurance for you and your dependents, with Tightknit covering 100% of the premiums. In other countries, we provide high-quality supplemental health insurance for you and your dependents, also fully covered by us.

We might be a startup, but we do not think that way. Our success hinges on great people and on creating an environment where they can be happy and healthy while feeling challenged to do their best work. We are intentional about the environment we want to create, and we hope this excites you to join us.

Also, we love otters here. 🦦

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