Founding Engineer - Full Stack (In Person Toronto)
Dimely · CA ·
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Dimely · CA ·
Dimely (YC S24)
Full-time
Three people. Years of runway. Scaling technology companies including Checkr and Forward Networks run critical billing workflows on Dimely today.
We read customer contracts and order forms, validate the billing terms inside them against company rules and source systems, catch discrepancies before they reach an invoice, and sync accurate data into systems like NetSuite, QuickBooks, Rillet, Salesforce, and Stripe.
We’re not trying to build a small software company. We’re building Dimely to become a category-defining company in financial operations.
Contract terms are unstructured. Every system downstream of them is not.
At many scaling companies, someone reads an order form, interprets it, checks it against a CRM record and a rate card, and retypes the result into finance software. When that goes wrong, it creates billing delays, revenue leakage, reconciliation work, and accounting problems that can surface months later.
This is harder than it sounds.
Extraction has to be accurate on documents nobody designed to be machine-readable. The output has to be auditable, because a finance team will not hand you critical billing workflows until they can understand why the system made every decision.
Most of the interesting work is in the gap between "the model got it mostly right" and "a controller signed off on it."
That is the gap we are building for.
You are our fourth team member and one of the first engineers at Dimely.
You will own product areas end to end: talk to the customer, understand the problem, decide what to build, make the architectural call, ship it, and confirm it works in production.
There is no spec to hand off. You are responsible for getting from customer problem to working product.
One day you might be designing infrastructure for an AI-powered billing workflow. The next, you might be debugging a NetSuite integration, improving an exception-review interface, or talking directly with a finance team to understand why their process is breaking.
You will have a large amount of autonomy and a correspondingly high level of responsibility.
The specific problems will change.
Owning the outcome rather than the implementation will not.
You own outcomes, not tickets. Shipping code is not the goal. Solving the problem is.
You move without waiting for permission. If something important needs to happen, you move it forward.
You close loops. Problems do not disappear into Slack threads, Linear tickets, or somebody else's backlog.
You care about the whole product. Backend, frontend, infrastructure, integrations, customer experience, reliability, and documentation are all part of making the product work.
You hold a high bar on correctness. Customers depend on Dimely for workflows that affect invoicing, cash collection, and accounting.
You think like an owner. You make decisions based on what is best for the customer and the company, not just what falls inside your job description.
Scope here is not predictable. Priorities change, customer problems can be urgent, and some of what you encounter will be problems nobody at Dimely has solved before.
We expect you to be comfortable figuring things out.
Experience with finance, accounting, billing, NetSuite, Salesforce, or similar systems is useful, but not required.
We care much more about whether you can learn quickly, build excellent software, and take ownership of difficult problems.
Dimely is built primarily in TypeScript, Next.js, and React, with a production codebase already supporting real customers and critical billing workflows.
You will not be joining a pristine greenfield project. You will inherit systems that have evolved quickly as we learned from customers, and you will have significant freedom to improve, rethink, or replace parts of the architecture that will not scale with where we are going.
We are still early enough that many of the most important architectural decisions are ahead of us.
**Be extremely early.**
You’ll be our fourth hire and one of the people who defines what the company becomes.
**Own something meaningful.**
Major parts of Dimely will exist because you built them.
**Work on difficult engineering problems.**
We sit at the intersection of AI, financial infrastructure, workflow orchestration, enterprise integrations, and systems where correctness matters.
**Build AI that does real work.**
AI at Dimely is part of operational systems that affect how companies invoice customers and manage revenue. It is not a chatbot layer or a demo.
**Work directly with customers.**
You’ll see what breaks, understand why it matters, and have the ability to fix it.
**Solve an expensive problem.**
Billing errors and delays directly affect cash collection, revenue visibility, accounting operations, and the customer experience.
**Shape the architecture.**
You’ll help design the systems that take Dimely from today's customers to hundreds and eventually thousands of companies.
**Help build the team and culture.**
As one of the first engineers, you will influence engineering standards, development practices, how we use AI, and who we hire next.
**Work with a small, ambitious team.**
You’ll work directly with co-founders Peter (Waterloo ECE / ex-Facebook) and David (Wharton / ex-Silver Lake).
**Meaningful equity and meaningful impact.**
You are joining early enough that your contribution can materially affect both the company and your career.
There will be ambiguity, changing priorities, difficult technical problems, and situations where there is no existing playbook.
We operate with urgency. We expect people to take responsibility, close loops, and work hard on the problems that matter most.
If you want clearly defined tickets, predictable scope, and narrowly defined responsibilities, this probably is not the right role.
If you want to build important systems from the ground up, work directly with customers, solve difficult problems, and have an outsized impact on what Dimely becomes, we’d love to talk.