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 technical leader to join a scaling organization at a pivotal stage, with a meaningful opportunity to grow into a broader Director-level mandate as scope and results warrant.
We are looking for someone who has been there before, a leader who has driven technical direction and built organizational structure through a similar growth stage, who knows how to bring architectural rigor to a fast-moving organization, and who can turn a group of strong individual team leads into a durable, well-run technical function.
You will work alongside the current engineering leader and the existing C-suite in a highly collaborative environment where Engineering is a strategic partner to the business. This is an opportunity to help shape what comes next.
The Mandate As a Principal Software Engineer, you will combine deep technical ownership with direct leadership of four team leads, helping the organization build the structure it needs to scale.
Your mandate will include:
Directly manage four team leads across product engineering, logistics engineering, customer engineering, and special projects
Act as a top-level technical authority, partner closely with the current engineering leader on architecture, technical planning, and roadmap execution
Make and support high-quality technical and system-level design decisions at scale
Coach and develop team leads, improving their technical decision-making and management capability
Formalize and evolve engineering processes: 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, both technical and organizational. 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 impact that support a path to a broader Director-level mandate.
Who You Are You are an experienced technical 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, or Engineering Manager at a scale-up, and ready for a meaningful increase in scope, including formal ownership of direct reports.
You have a solid full-stack engineering background,



having climbed the technical ladder and remained hands-on even as you've taken on people 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 managing and coaching team leads, and helping first-time or emerging managers grow.
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 directly managing and 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, whe

📌 Principal software engineer (Toronto)
🏢 HRXConnect
📍 Toronto