Director, Revenue

We are hiring for one of Canada’s fastest growing technology companies, recognized by Deloitte as the #1 Enterprise Software company in the 2025 North American Technology Fast 500 and ranked #5 in Deloitte Canada’s 2024 Technology Fast 50 Companies to Watch.

This is a rare opportunity for an accomplished revenue leader to join a high-growth company at a pivotal stage of its journey, with a meaningful opportunity to grow into a broader executive revenue mandate as the organization scales.

We are looking for someone who has been there before. A builder who has taken a revenue organization from the $10M stage toward $50M, who knows how to segment a go-to-market motion, stand up outbound where none existed, and turn a talented but early-stage team into a scalable engine.

You will work closely with founders and company leadership in a highly collaborative environment where Revenue is a strategic partner to the business, not a function waiting for direction.

This is an opportunity to help shape what comes next.

The Mandate

As Director of Revenue, you will build and evolve the revenue function to support the next stage of growth, with a transparent track toward a VP-level mandate as scope and results warrant.

Your mandate will include:

- Own enterprise, mid-market, and SMB sales as a unified revenue organization
- Lead SDR/BDR and business development, sales enablement, sales process, partnerships (initially), and revenue operations
- Build a scalable revenue organization rather than simply manage an existing one
- Segment the sales organization cleanly across SMB, mid-market, and enterprise
- Establish a repeatable, coachable enterprise sales motion
- Build an outbound SDR/BDR engine from a motion that is currently inbound-heavy
- Develop verticalized go-to-market motions across priority segments as the business expands
- Improve pipeline conversion, customer segmentation, expansion opportunity capture, partnership pricing, forecasting, metrics, and operating cadence
- Recruit and develop future specialist revenue leadership as the organization scales

In your first 90 days, you will diagnose the current organization, team capability, customer base, pipeline health,



and conversion gaps; recommend an org design and segmentation model; build the outbound strategy and SDR operating model; define the enterprise motion and go-to-market priorities; establish sales process, enablement, and metrics discipline; and deliver a practical plan for your first year alongside a longer-term view of the organization you're building.

Who You Are

- You are an experienced revenue leader who has already built something at a comparable stage of growth, you've run this playbook before, not just studied it.
- You have hands-on experience building or restructuring B2B SaaS revenue organizations in the $10M–$50M ARR range.
- You understand how to design and launch an enterprise motion, including quota models, deal cycles, and the discipline a more complex sale requires.
- You know how to build outbound from scratch, standing up SDR/BDR functions and pipeline generation where a business has historically relied on inbound.
- You are commercially sharp: fluent in recurring-revenue and usage-based models, pipeline conversion, forecasting, and where margin and leakage tend to hide.
- You think in systems and segmentation before you think in headcount, and you have a track record of building repeatable process rather than relying on individual heroics.
- You are a leadership builder who wants to develop the next layer of specialist revenue leaders as the organization grows.
- You bring a collaborative, low-ego style, you're motivated by building something well with others, not by proving you're the smartest person in the room, and you're comfortable challenging leadership constructively rather than simply agreeing.
- You ask thoughtful diagnostic questions before proposing solutions, and you're wary of leaders who skip straight to answers.
- You are a hands-on operator who will join calls, work deals directly,



and build from the ground up rather than manage from a dashboard.

You bring:

- 8–10+ years of B2B SaaS revenue leadership experience
- A proven track record of building or restructuring revenue organizations at the $10M–$50M ARR stage
- Experience across enterprise sales, outbound pipeline generation, SDR/BDR leadership, go-to-market design, quota models, partnerships, and customer expansion
- A solid understanding of recurring-revenue and usage-based business models
- Vertical SaaS experience, particularly in healthcare or telecom, is a plus
- The ability to operate strategically while staying close enough to the details to catch what others miss
- A collaborative, low-ego leadership style paired with the confidence to challenge and be challenged
- Comfort with autonomy and full accountability for outcomes
- Experience thriving in fast-moving, entrepreneurial environments where the organization is actively scaling

Why This Role

You will join at a moment when the revenue organization has real momentum and an even bigger ambition ahead of it. This is the first and most urgent senior revenue hire the business is making, and the role is being built around real ownership: the room to diagnose, design, and run the organization your way, not a seat where you're waiting for permission to make calls you're already qualified to make.

You will have the opportunity to build the revenue engine, develop the leaders beneath you, and shape how the business scales into its next stage of growth.

Compensation includes a competitive base salary, performance-based variable compensation, and equity. For the right leader, this role carries a meaningful path to grow into a broader executive revenue mandate as the company scales, though specific future titles and timelines will depend on performance and business needs rather than being guaranteed at the outset.

If you've built something at this stage before and you're ready to build what comes next, this could be the opportunity you've been waiting for.

Compensation for this role: CAD 150,000–185,000 base + on-target earnings (OTE), with performance- and activity-based incentives tied to agreed targets.

📌 Director of Revenue (Toronto)
🏢 HRXConnect
📍 Toronto