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

Founder-led sales, customer referrals, and strong partnerships have built a business that restaurants trust. Now we're ready to grow faster, and we're hiring our first marketer to lead the way.

As our Head of Marketing, you'll own pipeline growth and build Actual's marketing from the ground up.

You'll report to the CEO and work closely with Sales and Customer Success every day. Some of the groundwork is already done: partner webinars have restarted with more on the calendar, and an end-of-year offer is in the works. You'll take these over and decide what to scale, change, or stop.

This role is about building our marketing machine: launching channels, testing quickly, and making fast calls on where to double down. You'll start as a team of one. Around six months in, once we can see which channels are working, you'll have the opportunity to build a team under you to speed up growth.

Success means qualified demos booked and pipeline created every month, a partner channel that delivers on a regular schedule, and at least one more channel producing predictable demos within six months.

What you'll own

  • In your first few months:

    • An audit and a plan. Within 30 days, review our channels, partners, and current pipeline sources: what's working, what's stalled, and what's never been tried. Turn that into a 90-day plan with clear targets, budget asks, and the first tests you want to run.

    • Our customers and sales process. Get to know the restaurants and hospitality groups we serve, how they buy, and how our Sales team runs a deal.

    • A regular rhythm. By 90 days, have the partner channel, outbound campaigns, and a customer referral program running on a regular schedule.

    Over the year:

    • Pipeline growth. Qualified demos booked and pipeline created each month are your numbers. Report weekly in HubSpot on leads, demos, cost per demo, and pipeline by source.

    • The partner channel. Build our relationships with provincial restaurant associations and technology partners (POS, payroll, and similar). Run the joint webinars, member emails, and co-marketing that come out of those partnerships, and get partner-sourced pipeline back to where it was and beyond.

    • Outbound with Sales. Plan and launch outbound campaigns organized by province, venue type, and partner, with shared pipeline targets.

    • A referral program. Turn happy customers and platform users into a repeatable source of demos.

    • Paid tests. Decide where paid digital (LinkedIn, Google, Meta) or an ad agency makes sense. Run small tests, read the results, and scale what ties back to demos and revenue.

    • Marketing vendors. Own our relationships with marketing agencies and vendors, and hold them to results.

    • The Actual name. Keep us top of mind with customers and prospects through newsletters, customer stories, industry reports, and events.

    • Your team. Once the first channels are working, hire the people who will help you scale them.

What we're looking for

  • B2B marketing with a pipeline number. 7 to 10 years in B2B marketing, with at least 3 years owning pipeline or demand generation.

  • Startup experience. Time at a Series A to B company or similar stage, ideally as the first or an early marketing hire.

  • Demand generation across several channels. A track record you can point to, with results.

  • Partnership and channel marketing. Associations, resellers, integrations, and co-marketing, plus webinars and events from promotion through follow-up.

  • Hands-on HubSpot. Workflows, email, lead tracking, and reporting. You build these yourself.

  • Budget and vendor management. You've managed agencies, freelancers, and a marketing budget.

  • Comfort with numbers. Cost per lead, cost per demo, and pipeline reporting are part of your week.

  • Strong writing. A good eye for messaging and the ability to write it yourself.

  • Canadian market experience. Based in Canada, with experience marketing to Canadian customers (preferred).

Helpful, not required: hospitality, restaurant tech, POS, payroll, or fintech experience; an SMB or vertical SaaS background; experience with a rebrand or name change; PR and industry reports; existing relationships in the Canadian or US restaurant ecosystem.

Before you apply

For the first six months, you'll be our only marketer. You'll write the emails, build the HubSpot workflows, and host the webinars yourself, bringing in agencies and freelancers where they help.

You'll likely thrive here if you've owned a pipeline number and like being measured on demos and revenue. It may be a harder fit if most of your experience is in brand or awareness work, if you've mainly managed agencies rather than doing the work, or if you've specialized in one channel such as SEO, paid, or content. The same goes if you prefer planning to shipping, or like to commit budget before you've tested an idea.

How we work

We're a small organization, around thirty people across the company, which means your work is visible and your judgment carries weight. Marketing will sit right next to Sales and Customer Success, and you'll have a direct line to the CEO. Everyone here uses AI tooling as a normal part of the job, and we expect the same of marketing.

We're remote-first with a distributed team, and we're honest about the tradeoffs that come with it: strong written communication matters more here than it would in an office.

Compensation and details

  • Compensation: Base salary, plus a performance bonus tied to qualified pipeline created, plus stock options

  • Location: Remote in Canada

  • Reports to: CEO

  • Full-time permanent position

How to apply

Click here to submit your details https://bsxn99lvr70.typeform.com/to/dYCyfY1t. We're most interested in one specific thing: tell us about a channel you took from untested to producing predictable demos or pipeline, what you tried that didn't work, and how you knew when it did.

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.