Why this role exists

We've reached the stage where "operations" is spread across several leaders and, often, the CEO. We're hiring a full-time Head of Operations to become the operational backbone of the company: to consolidate the run-the-business functions into one coherent org, build the systems and cadence that let us scale cleanly, and free the founders to stay on product, growth, and the relationships that move the business.

You'll be the full-time operational anchor alongside a fractional CFO and VP of Sales, and a true partner to the CEO through a pivotal growth chapter. This is a senior leadership-team role with broad ownership and a clear path to grow into a COO mandate.

How you'll build it, AI-native, from first principles

We're an AI company, and we want operations built the way we build our product: not by importing the standard SaaS playbook, but by asking what each function should look like now that AI can do so much of the work.

• First principles over best practices. Treat the conventional playbook as a data point, not an answer. Start from the real problem and the outcome you want, then design the leanest path to it, even if it looks nothing like how it's "supposed" to be done.

• AI-native by default. Assume AI and automation are the first tool, not the last resort. The question is rarely "who do we hire to do this?" and more often "how much of this should a human do at all?" Build a team and processes that are small, leveraged, and AI-augmented from day one.

• Curiosity as a discipline. Meet every operational problem, a clogged funnel, slow onboarding, a compliance burden, with genuine curiosity about why it works the way it does before deciding how to fix it. The good answers usually aren't in the textbook.

What you'll own

The mandate in every domain below is the same: build the AI-native version, not the legacy one.

1. The operating system & cadence

Run the company's operating rhythm: annual/quarterly planning, OKRs and goal-setting, and the leadership-meeting and board-prep cycle.

Drive cross-functional execution and program management, turning strategy into shipped outcomes across teams.

Act as the CEO's force multiplier on special projects, including operational quarterbacking of financing and strategic initiatives alongside the CFO and our advisors.

2. People & Culture

Own the People function: hiring velocity (we have several open roles and are scaling), onboarding, and performance and compensation frameworks.

Steward culture and team health as headcount grows.

3. Revenue & Business Operations

Own RevOps/BizOps, the systems and data beneath the funnel: CRM (HubSpot) hygiene, pipeline and SLA reporting, lead definitions (MQL/PQL), and billing and renewals operations.

Make the business measurable and the go-to-market machine efficient; partner closely with Sales, Marketing, and Customer Success.

4. Security, Privacy & Compliance

Own the trust backbone of a healthtech company: SOC 2, PHIPA/PIPEDA compliance, data governance, information security, and vendor security reviews.

Turn security and privacy into a competitive advantage in enterprise sales and a clean story in any diligence.

5. Legal, Vendor & Corporate Operations

Manage contracts, vendors, and procurement (including partner and platform agreements), and coordinate legal and corporate administration.

Keep the corporate operating foundation tidy and audit-ready.

What success looks like

First 90 days: you've mapped the operational surface area, taken ownership of People and RevOps, established the leadership operating cadence, and stabilised the basics (CRM hygiene, reporting, the financing data room).

6 months: clear OKRs and reporting the leadership team runs on; a People engine keeping pace with hiring; a defined, instrumented funnel (MQL → PQL → paying); a credible security & compliance roadmap underway.

12 months: operations is a durable, scalable backbone rather than a set of heroics, and the CEO's time has visibly shifted from running the business to growing it.

What we're looking for

Must-haves

8+ years in operations, including senior operational leadership at a startup/scaleup (Series A–C), ideally in B2B SaaS.

Hands-on experience standing up and running at least two of: RevOps/BizOps, People/HR, Security/Compliance, IT.

A player-coach, equally comfortable setting strategy and doing the work. This is a builder's role, not a delegator's.

An AI-native operator, you reach for automation and AI first, and have built (or rebuilt) processes around what AI can now do, not around how things were done before.

A first-principles, curious thinker, you treat best practices as inputs, not defaults, and you'd rather take a problem apart and understand it than copy someone else's solution.

Strong systems and data instincts; fluency with operational tooling (CRM/RevOps, HRIS, and the like).

High trust, low ego, calm under ambiguity, and excellent judgment about what to prioritise and what to let go.

Bonus

Healthtech or another regulated industry; familiarity with PHIPA/PIPEDA, SOC 2, or healthcare data.

Experience supporting a financing round or other strategic corporate process operationally.

Canadian healthcare-system context; HubSpot depth.

What this role is not

This is not finance leadership (our CFO owns FP&A and capital), not product or engineering (owned by the CTPO), and not sales leadership (owned by the VP of Sales). The Head of Operations makes all of these run better, owning the operational systems beneath them, rather than owning their outcomes

Team & reporting

Reports to the CEO and sits on the leadership team. Inherits the People & Culture and Revenue & Business Operations functions (each with an existing lead) plus an incoming GTM Ops Engineer, and builds out Security/Compliance and IT.

• Remote and hybrid work options & flexible work hours
• Comprehensive health and wellness coverage from day one
• Competitive PTO, including winter shutdown Dec 25 - Jan 1, birthdays and Taliversaries, and 'extra long' long weekends
• $2000 annually in "Knowledge Dollars" to learn, grow, and level up
• Quarterly socials & company outings that bring our team together beyond the day-to-day

170000 - 220000 CAD a year