Principal 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 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 strong 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, where core technical and organizational problems are typically already solved
- A track record of balancing hands-on technical credibility with people leadership, you can still review code or weigh in on architecture, but you don't need to be the smartest engineer in the room to lead effectively
- Judgment for when to build process versus when process would slow the team down, especially in ambiguous, fast-changing environments
- Experience hiring and interviewing engineers and engineering leaders, including defining role scope and leveling criteria from scratch
- Comfort operating with incomplete information and revisiting decisions as the organization's needs evolve, rather than defending a framework once it's built
- A track record of translating ambiguous business or technical goals into a clear team structure, roadmap, or set of priorities
Our Stack
- Languages/Frameworks: TypeScript, NodeJS, React
- Database: MongoDB
- Cloud/Infra: AWS, Terraform
- APIs: REST APIs at scale (1B+ requests/month)
- Integrations: CRM & ERP platform integrations, third-party API ecosystems
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 reporting to 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 mandate, though the specific timeline and scope will depend on performance and business needs rather than being guaranteed at the outset.
