Staff Software Engineer, Technology

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 engineering leader to join a scaling organization at a pivotal stage, with a meaningful opportunity to grow into a broader Director-level engineering mandate as scope and results warrant.

We are looking for someone who has been there before. A leader who has scaled an engineering organization through a similar growth stage, who knows how to build formal structure where none yet exists, and who can turn a group of strong individual team leads into a durable, well-run organization.

You will work alongside the current engineering leader, existing C-suite in a highly cooperative environment where Engineering is a strategic partner to the business.

This is an opportunity to help shape what comes next.

The Mandate

As a Staff Software Engineer, you will build and evolve the engineering function to support continued growth, with a clear track toward a Director-level mandate as the organization matures.

Your mandate will include:

- Oversee four team leads and their teams: product engineering, logistics engineering, customer engineering, and special projects
- Partner closely with the current engineering leader on architecture, technical planning, roadmap execution, and identifying organizational gaps
- Make and support high-quality technical and product-level engineering decisions
- Coach and develop team leads, improving their decision-making and management capability
- Formalize and evolve engineering processes, including career progression, work allocation, coaching, planning, and execution frameworks
- Build scalable operating rhythms, policies, and documentation where progression and process are currently informal
- Ensure urgent, cross-functional work can be absorbed without derailing committed roadmap work
- Collaborate effectively with C-suite leaders and other incoming Director-level hires

In your first 6–12 months,



you will get close to each team and its work, build trust with the team leads, and identify where structure is missing. You will formalize career progression and performance frameworks, establish clearer planning and execution cadences, and put in place the documentation and policies the organization needs as it grows. You will also take on a growing share of architecture and roadmap decision-making alongside the current engineering leader, and demonstrate the judgment and organizational impact that support a path to a broader Director-level mandate.

Who You Are

- You are an experienced engineering leader who has already scaled an organization through a comparable growth stage, you've built this kind of structure before, not just read about it.
- You are likely operating today as a Staff+, Senior Staff, Principal, Engineering Manager, Senior Manager, or Director at a scale-up, and ready for a meaningful increase in scope.
- You have a strong full-stack engineering background, having climbed the technical ladder before moving into broader leadership.
- You have built or significantly improved engineering processes, career progression frameworks, and planning cadences in an organization that didn't have them yet.
- You are a strong people leader, comfortable coaching first-time or emerging managers and helping them grow into stronger leaders.
- You bring excellent written and verbal communication, and can point to real evidence of it, technical writing, conference talks, or a track record of clear communication with technical and non-technical audiences alike.
- You are comfortable operating hands-on in an evolving organization with incomplete processes, rather than expecting a fully built environment.
- You bring a collaborative, low-ego style,



you're motivated by building something well with others, and you're comfortable challenging leadership constructively rather than simply agreeing.

You bring:

- Demonstrated success scaling an engineering organization in a startup or scale-up environment, ideally at a stage beyond where this organization is today
- Strong systems, architecture, and full-stack engineering judgment
- A track record of developing team leads, managers, or other emerging leaders
- Experience formalizing engineering processes: progression frameworks, work allocation, coaching structures, and execution rhythms
- Excellent written and verbal communication skills, with concrete examples to draw on
- Comfort partnering with a current organizational leader rather than operating in a vacuum
- Willingness to work hybrid, based in or near Toronto
- Experience at a company outside of large, established tech organizations, where the core technical and organizational problems are typically already solved

Why This Role You will join at a moment when the engineering organization has real technical talent and strong team leads, but is still building the formal structure it needs to scale further. This role is being built around real ownership: partnering closely with the current engineering leader today, and growing into independent ownership of architecture, planning, and organizational decisions as you establish trust and track record.

You will have the opportunity to build lasting structure, develop the leaders beneath you, and shape how the engineering organization scales into its next stage of growth.

For the right leader, this role carries a meaningful path to grow into a broader Director-level engineering mandate, though the specific timeline and scope will depend on performance and business needs rather than being guaranteed at the outset.

If you've scaled an engineering organization through this stage before and you're ready to build what comes next, this could be the opportunity you've been waiting for.

Compensation:

160K - 180K Base CAD per year, plus annual performance bonus and comprehensive benefits.

📌 Staff Software Engineer (Greater Toronto Area)
🏢 HRXConnect
📍 Greater Toronto Area