About Actual™

Hospitality is built on actuals, that's not just our tagline, it's how we operate. At Actual™, we're building the payment infrastructure hospitality businesses run on, moving millions of dollars in hard-earned tips directly to the employees who earned them. No cash envelope, no spreadsheet, no two-week wait.

Our flagship product, Actual™ Tips, handles tip pooling, instant tip payouts, cashless tip distribution, reporting and compliance, so operators can eliminate manual admin and reduce payroll burden. Beyond tips, Actual Ops gives operators a live view of labor cost, cost of goods sold, purchases and data-driven sales forecasts, replacing gut-based scheduling decisions with real numbers. And Actual Payroll extends that same automation to payroll itself, built specifically for hospitality operators and their teams.

Backed by N49P, Northside Ventures, Union Capital and other investors, we're trusted by restaurants, hotels and coffee shops across Canada to move real money reliably. The numbers you can trust.

The role

Getting a restaurant group live on Actual is the hardest, most consequential work we do.

For our more straightforward customers, onboarding is close to self-service. For those looking to benefit from automation, the work required to integrate the point-of-sale (POS) and scheduling systems with complex tip division rules requires implementation work: mapping sales and tips data with employees schedules across systems that provide overlapping datapoints,  configuring tip division rules based on the unique operational style of each business, validating it against live data, training customers and staying with them until the first payouts run clean.

We're hiring because we're growing fast and our customers' needs are often complex. Implementation has become a function of its own at Actual and we're building out the team that owns it.

You'll own the customer journey from signing to successfully processing. You'll sit with our engineering team, working directly with the developers who build our integrations, and report to the VP of Engineering.

You won't be figuring it out alone. You'll join alongside the specialist who built this function, as a peer doing the same job, with a substantial overlap to learn our systems, our customer’s evolving needs, and helping build and document the process for scale.

What you'll own

  • The implementation itself. Advanced and integrated onboardings end to end: intake and scoping, POS and scheduling integration setup, role and department data mapping, tip model configuration, validation against real payroll periods and customer training. You will be the person who knows whether a configuration is actually right.

  • The handoff. Implementation isn't finished when the config is done - it's finished when the customer has run a payment cycle or two and an account manager can take them on with confidence, using documentation that shares all the details so that the day to day can be managed by account managers and support team. You'll own that transition and the checklist that gates it.

  • Capacity and pipeline visibility. Sales needs to know what's realistic before they commit to a customer, not after. You'll keep a clear picture of what's in flight, what's blocked and on whom plus when capacity frees up.

  • Making the next implementation easier than the last. We're always trying to improve our implementation and onboarding processes. You'll build reusable intake, training material and documentation, and you'll be a direct voice in the product decisions that reduce how much bespoke configuration we need in the first place. Our engineering direction is moving toward standard configurations and away from per-location customization, and the implementation perspective has a lot of say in how we do that.

  • Being the subject matter expert. Sales asks whether a tip model is supportable. Support asks whether something is a bug or a misunderstanding. Engineering asks what the customer actually meant. You will be able to answer to all three, and part of the job is building enough shared knowledge that others will be able to do the same.

What we're looking for

  • You've done this job before. At least a few years as an implementation specialist, or in onboarding, solutions or technical account management, configuring a SaaS product for external customers. At the complex end of it: integrations, data migration, setups that vary customer to customer.

  • Translating how a business operates into how a system is configured. An operator describes their tip model in their own words, in their own order, with the exceptions they forgot to mention. You turn that into a configuration that pays people correctly. This is the heart of the job.

  • Real systems literacy. You should be able to reason about how data flows between two systems, spot why a match failed, read an API's output well enough to know whether the problem is the integration or the customer's data and hold an accurate model of a complicated product in your head. To be clear, you don't need to write code and we're not looking for a developer. We are looking for someone who understands how systems work.

  • Fluency with messy data. Employee lists, role mappings, POS exports, spreadsheets that disagree. Much of this work is careful reconciliation, and being good at it is a skill we take seriously.

  • Composure under pressure. This work runs to deadlines and involves people's earnings, so questions tend to arrive with urgency attached. You stay calm, stay solution-oriented and keep the customer confident while you work it through.

  • Customer-facing confidence with operators. You'll be training general managers and restaurant owners, and sometimes helping them improve their own processes. That takes directness and patience in the same conversation.

  • The judgment to work out what's actually broken, and explain it in both directions. Turning a customer's account of what went wrong into something an engineer can act on, and an engineer's answer into something an operator can use. Knowing what to escalate and what to solve yourself.

  • Initiative and curiosity. You go and find out. When something doesn't add up you dig into it rather than filing it, and you're the kind of person who wants to know why a system behaves the way it does.

  • Strong written communication and self-direction. We're remote and distributed across Canada and Europe. You will be expected to anticipate what's next and plan your work accordingly.

  • Comfort building the process you're working inside. The dedicated implementation function at Actual is less than a year old. Some of what you need does not exist yet.

What will make you stand out: experience implementing or supporting hospitality technology - POS, payroll, scheduling, HR or tip management (Toast, Squirrel, Push, Silverware and their equivalents); hands-on knowledge of tip models, tip pooling, tip-outs and service charge structures, and the rules that govern them; having worked in restaurants yourself; payments or payroll domain knowledge; having been an early hire on an implementation or professional services team.

What this role is not

We'd rather be direct than have you find this out in week three.

It isn't account management. You aren't carrying a book of accounts or owning renewals. You own customers through implementation and then genuinely hand them off - our account management team takes it from there, and we're strict about that boundary.

It isn't a development role. You'll work closely with engineers, you'll file the ticket, sometimes you'll be the reason a bug gets found but you won't be building the integration.

It isn't purely project coordination. Tracking the work is a small part of it. Knowing the product deeply enough to configure it correctly is the job.

And to be straight about the state of things: today, nearly every integrated customer is configured somewhat differently, our documentation is thinner than we'd like and there is a backlog. We're actively fixing all three, and you would have real influence over how. If that sounds like an interesting problem, we should talk.

How we work

We're a small company - around thirty people - which means your work is visible and your judgment carries weight. Implementation sits with engineering rather than off to the side, deliberately: it puts you next to the people who build the thing, and it means product decisions hear from you early rather than after the fact.

We're remote-first and honest about the tradeoffs: strong written communication matters more here than it would in an office.

Compensation and details

  • Salary: $55,000 - $105,000 CAD, based on experience

  • Location: Remote within Canada

  • Full-time permanent position

How to apply

Click here to submit your details - https://bsxn99lvr70.typeform.com/to/dYCyfY1t . We're interested in one thing specifically: tell us about the most complicated customer implementation you've run - what made it hard, and what you'd do differently now.

No cover letter template required. We read every application.

Actual is an equal opportunity employer. We welcome applications from people of all backgrounds and are committed to building a team that reflects the diversity of the industry we serve. Accommodations are available on request at any stage of the hiring process - just let us know what you need.