Build AI that liberates people at work.
You’ll spend your time solving problems that actually move the needle for a real business, not managing process for its own sake.
James Stolp
chief product officer
How we work.
Small team, real ownership
See a problem, solve it. You're never more than three layers from the decision.
Ship, learn,
improve
We make reversible decisions quickly, because working solutions beat perfect prototypes.
AI-native, not AI-curious
We use Claude, ChatGPT, Cursor and more. Daily, not occasionally.
Trust over
process
We hire experienced people and get out of their way. Judgment matters more than rules.
Direct access to founders
Leadership is in the work. You'll build with them, not just report to them.
Feedback is
a feature
We give candid feedback because we respect each other enough to help everyone grow.
WHO YOU'll BE WORKING WITH
Operators who choose to come back and build the hard thing.
Contextual is a team of serial entrepreneurs and operators who've built and scaled successful companies before. People who recognize opportunities, who've been in the weeds, know what good looks like, and choose to come back to build the hard thing.
Our values mean a lot.
Collective ownership
We show up as stewards of shared success, not lone heroes. We take initiative, deliver on commitments, and invite others early to make outcomes stronger.
What this looks like
- You don't wait for permission to solve problems you can see.
- You follow through on commitments, even when it's hard.
- You ask "what can I do?" instead of "whose job is this?"
What this doesn't mean
Working alone, refusing help, making solo decisions on things that affect others.
Mutual respect
We create an environment where people speak openly, listen well and take each other seriously. We value good judgment, clear communication and the experience people bring to the work.
What this looks like
- You challenge directly, but always with good intent and courtesy.
- You listen first, then respond clearly and practically.
- You assume people want to do good work, and make it easier for them to do it well.
What this doesn't mean
Dismissing other views, talking over people, acting superior.
Bias for action
We move quickly, learn fast and keep improving as we go. We favor practical progress over perfect plans and complicated processes.
What this looks like
- You test, learn and iterate quickly, aiming for working solutions.
- You make informed decisions fast, then adjust when the work tells you something new.
- You look for the shortest path to real value, not the longest path to polish.
What this doesn't mean
Chasing perfection, over-designing problems, slowing delivery with needless process.
Steady under change
We adapt when the work changes, because delivery in real businesses is never a straight line. We keep our sense of purpose intact, even when the path to the outcome shifts.
What this looks like
- You stay grounded when things change and keep moving toward the outcome when the path shifts.
- You learn from setbacks, then use what you’ve learned to improve.
- You stay calm, flexible and focused when the work gets messy.
What this doesn't mean
Getting stuck in frustration, blaming others, treating change as a barrier.
Customer first
We judge our work by the difference it makes to the customer’s business and their people. If something doesn't improve their everyday reality, it’s not enough.
What this looks like
- You start every decision with the impact on customers’ day-to-day work.
- You focus on removing friction, reducing bottlenecks and helping teams get real work done.
- You think about trust, usability and long-term usefulness.
What this doesn't mean
Building for convenience, hiding trade-offs, losing sight of customer goals.
how we hire
Hiring, run like delivery.
The people who interview you are the people you'd work with, founders included. Honest and straightforward, no corporate fluff.
01
Apply
Through the links below. A resume or LinkedIn profile and a few sentences on why this role.
From you: 10 minutes
02
Conversations
With the people you'd work with, founders included. Real questions about real work.
From you: 2-3 conversations
03
Practical
A role-specific exercise that looks like the actual work.
From you: a few focused hours
04
Decision & checks
A clear yes or no. Enterprise work means background verification and security training before system access; we say so up front.
From you: documents for verification
05
Onboarding
Security awareness training on day one, then straight into real work alongside a senior teammate.
From you: your first shipped work
Our open roles.
NOTHING THAT FITS RIGHT NOW?
Introduce yourself.
We add roles through the year as the team grows. Tell us who you are and we'll be in touch about roles. Nothing more.
Thank you! Your submission has been received!
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What you get.
Capability and commitment deserves fulfilment and reward.
Here’s what that looks like.
Here’s what that looks like.
Competitive pay
A salary and benefits package that takes experienced people seriously.
Unlimited vacation
And we encourage you to take it. That part is policy, not a poster.
Flexible by design
Remote working and flexible hours, shaped around how you work best.
Room to grow
We're scaling and adding roles through the year. Growth here means more scope, not more layers.
A team that has your back
Collaborative and inclusive, and candid with it; because we respect each other enough to be honest.
Work that ships
Real solutions for real businesses, live in weeks, with AI in your toolkit every day.
Ready to build with us?
