Senior 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 Rapid 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, Revenue, you will design and execute the go-to-market strategy across new business, expansion, and partnerships, and help take the business from its current stage toward its next major scale milestone.

Your mandate will include:

Revenue Strategy & GTM

- Own and execute the company's revenue strategy across new business, expansion, and partnerships
- Develop a scalable GTM model across SMB, Mid-Market, and Enterprise
- Establish clear ICPs, segmentation, territories, quotas, and coverage models
- Identify priority verticals and build repeatable vertical GTM motions
- Develop the organizational structure, talent plan, and operating model required to scale revenue

Sales & New Business

- Lead and evolve the sales organization across SMB, Mid-Market, and Enterprise
- Build a repeatable enterprise sales motion focused on business value, ROI, and executive-level selling
- Establish sales methodologies, qualification frameworks, pipeline standards, and forecasting discipline
- Increase ACV and improve win rates and sales velocity
- Build a scalable sales management and coaching culture

Outbound & Pipeline Generation

- Transform the current SDR function from primarily inbound qualification into a predictable outbound pipeline engine
- Define TAM, account segmentation, targeting, and outbound strategy
- Build vertical and account-based outbound programs
- Establish SDR/AE alignment, productivity metrics, and pipeline accountability
- Create predictable pipeline coverage across each revenue segment

Customer Expansion

- Build a structured customer segmentation and expansion strategy
- Partner with Customer Success to establish differentiated engagement models for SMB, Mid-Market, and Enterprise customers
- Identify usage, product adoption, and customer growth signals that create expansion opportunities
- Build cross-sell, upsell, and expansion motions
- Establish accountability for GRR, NRR, and Expansion ARR

Partnerships

- Build a scalable revenue strategy across strategic, technology, and channel partnerships
- Define partner ICP, economics, incentives, qualification, and activation models




- Develop technology partnerships that embed the company's product into relevant software ecosystems
- Build channel relationships with agencies, consultants, resellers, and system integrators
- Establish measurable partner-sourced pipeline and revenue targets
- Work cross-functionally to develop appropriate SaaS and usage-based commercial models for partners

Revenue Operations

- Establish a unified revenue operating system across Marketing, SDR, Sales, Customer Success, and Partnerships
- Develop revenue dashboards and KPI frameworks
- Improve pipeline visibility, forecasting accuracy, and revenue predictability
- Establish consistent definitions and accountability across the revenue funnel
- Partner with RevOps to improve territory planning, compensation, reporting, and sales productivity

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 are highly entrepreneurial, data-driven,



commercially sophisticated, and obsessed with revenue predictability.
- You are comfortable moving between strategy, organization, process, pipeline, deals, and metrics, and can build the strategy with leadership in the morning and coach an AE on an enterprise opportunity in the afternoon.

You bring:

- 10+ years of experience in B2B SaaS, technology, or a comparable recurring-revenue business, including 5+ years in senior revenue, sales, or GTM leadership
- A proven track record of scaling a business through a significant growth stage, ideally from approximately $10M to $50M+ ARR or comparable scale
- Experience building and managing SMB, Mid-Market, and Enterprise sales motions
- Demonstrated experience building an SDR/BDR outbound pipeline motion
- Strong enterprise sales and value-selling experience
- Experience with customer expansion, renewals, and NRR
- Experience developing or scaling partner/channel revenue
- A strong understanding of SaaS economics, pricing, and unit economics
- Strong analytical, forecasting, and operational capabilities
- Experience hiring, developing, and managing high-performing revenue teams

Preferred Experience

- API or developer-focused SaaS
- Usage-based or hybrid SaaS plus usage pricing models
- Infrastructure, communications, fintech, healthcare, or telecom technology
- Vertical GTM experience
- PE-backed or high-growth SaaS environments
- Experience building revenue organizations during a major scale-up phase

The Type of Leader We Want The ideal candidate has built a revenue machine rather than inherited one. This role is not a fit for candidates whose experience is primarily:

- Managing a large, mature sales organization without having built it
- Running an established enterprise sales team with significant supporting infrastructure already in place
- Pure sales operations / RevOps
- Pure partnerships or alliances
- Relationship management without revenue ownership
- Managing large teams without direct experience building GTM systems
- Traditional enterprise sales leadership without SMB/MM or outbound experience

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.

📌 Senior Director of Revenue (Toronto)
🏢 HRXConnect
📍 Toronto