Director, Software Engineering & Innovation

Location: remote/Hybrid (Montreal/Sherbrooke)

Reporting to: Vice President, Platform & Engineering

Here's what we do and why we do it.

Simply put, we will work together to simplify businesses' IT with cloud technology so they can focus on what really matters. Discover how we do that here: 

About the role

We are looking for a Director, Software Engineering & Innovation, to lead a large engineering organization and help shape the next generation of how we build software at Sherweb. You will lead approximately 80 people through five managers and will be responsible for delivery, execution, engineering excellence, leadership development, and the evolution of our SDLC in an AI-enabled world.  

What makes this role different

This is a leadership role for someone who does not simply manage the current system but improves it. We want a leader who is curious, pragmatic, and comfortable experimenting with new practices before they become obvious industry norms. You will help teams adopt modern approaches such as Team Topologies, platform thinking, AI-assisted development, agentic workflows, and Spec-Driven Development where they create measurable value.

Who you are

You are a senior engineering leader with experience scaling teams, coaching managers, and delivering complex software products or platforms. You bring strong judgement, managerial courage, and the ability to have direct conversations while keeping trust and respect. You are serious about outcomes, but you do not take yourself too seriously. You bring energy, humility, and a work-hard/play-hard mindset that helps teams perform and enjoy the journey.  

Why this matters

AI is changing software delivery, but successful adoption requires more than tools. It requires clear intent, strong engineering discipline, modern leadership, secure guardrails, product alignment, and a culture willing to learn. This role will help Sherweb turn that opportunity into a repeatable operating advantage.  

How you will contribute to Sherweb's success

• Lead and scale a multi-team software engineering organization responsible for delivering high-quality, reliable, secure, and customer-focused products and platforms.  


• Create a culture where managers and teams continuously improve how they deliver value, not only what they deliver.  


• Champion and evolve modern engineering practices including Team Topologies, DevOps, platform thinking, AI-assisted development, and Spec-Driven Development where appropriate.  


• Develop leaders: coach five managers to become more autonomous, more courageous, more accountable, and better able to grow their own teams.  


• Build the next evolution of the SDLC by introducing practical AI-enabled workflows, guardrails, experimentation loops, metrics, and adoption patterns that improve quality, speed, predictability, and developer experience.  


• Act as a trusted partner to product, architecture, operations, security, finance, and executive leadership; connect technical execution to business outcomes.  


• Bring energy, clarity, and fun to the organization: work hard, create momentum, celebrate wins, and keep the team grounded without taking oneself too seriously.

Here's what your day-to-day will look like in this role.  

• Set and communicate a clear operating plan that connects department objectives, delivery priorities, engineering health, and Sherweb’s business strategy.  


• Lead, coach, and hold accountable a team of managers overseeing software development teams, platform capabilities, and delivery practices.  


• Drive execution across multiple initiatives by balancing customer outcomes, product priorities, architectural direction, operational reliability, security, and capacity constraints.  


• Introduce and scale new ways of working across the SDLC, including AI-assisted development, Spec-Driven Development, agentic coding workflows, quality gates, automated validation, and continuous improvement practices.  


• Partner with architecture leaders to ensure teams make sound technical decisions, manage complexity, reduce cognitive load, and evolve boundaries and team interactions intentionally.  


• Collaborate closely with product leadership to understand customer problems, product strategy, value streams, roadmap trade-offs, and delivery economics.  


• Strengthen management practices across recruitment, performance management, coaching, talent development, succession planning, compensation reviews, and engagement.  


• Identify high-potential employees and managers, create growth paths for them, and ensure key talent remains challenged, engaged, and visible.  


• Have direct and respectful tough conversations when required, take difficult decisions when they are the right ones, and coach managers to do the same.  


• Contribute to governance, audit, compliance, and operational practices, including SOC 2, PCI-DSS, ISO 27001, tax credits support, and internal controls.  


• Represent Sherweb’s values and help create an inclusive, open-minded, respectful, accountable, and high-performing culture.  

Required experiences and capabilities

• Significant experience leading software engineering organizations at scale, ideally 50+ people, with multiple managers reporting into the role.  


• Proven ability to coach managers, raise leadership maturity, build accountability, and develop succession capacity. 


• Strong experience delivering complex modern software products or platforms, ideally multi-tenant SaaS, API-centric, cloud-based, or high-scale web applications. 


• Demonstrated ability to modernize engineering practices across CI/CD, automated testing, code reviews, source control, observability, DevOps, security, reliability, and deployment practices.  


• Practical experience introducing AI into the SDLC, such as GitHub Copilot, agentic coding, AI-assisted reviews, automated test generation, AI-enabled documentation, or similar practices.  


• Familiarity with Spec-Driven Development, spec-first workflows, or equivalent approaches that use structured requirements, constraints, acceptance criteria, and validation as durable engineering artefacts.  


• Strong organizational design instincts; familiarity with Team Topologies, cognitive load, value streams, enabling teams, platform teams, stream-aligned teams, and interaction modes is a strong asset.  


• Excellent judgement, managerial courage, conflict resolution skills, and ability to make difficult decisions without drama.  


• Ability to partner with product leaders and understand product discovery, roadmap trade-offs, customer value, commercial impact, and delivery economics.  


• Strong communication skills with the ability to influence technical and non-technical stakeholders, including executive audiences.  


• Bilingual French and English, spoken and written, or strong ability to operate effectively in both languages.  

Nice-to-have experience

• Has led or partnered closely with product management in a SaaS or platform organization.   


• Has led platform engineering, developer experience, internal tooling, architecture, or technical enablement functions.  


• Has scaled AI adoption across teams using governance, enablement, communities of practice, secure tooling, and measurable adoption goals. 


• Has led organizational changes based on Team Topologies, Domain-Driven Design, platform operating models, or value-stream alignment. 


• Has experience with architecture leadership and could eventually lead or strongly influence architects and senior technical leaders. 

Benefits of working at Sherweb  

Sherweb is, above all, an environment where the needs of our customers are at the heart of our actions. We are committed to living our values of passion, teamwork and integrity every day.  

A fast-paced work environment that adapts to you  

• A friendly and diverse work culture with inclusion and equality at the heart of our actions  


• State-of-the art technology and tools  


• A results-oriented culture where talent, action, and thinking outside the box are given due recognition  


• Annual salary review based on performance  


• Generous and caring colleagues of various professional and cultural backgrounds  

A flexible total compensation offer  

• A base salary ranging between 112 140$ and 160 200$ yearly  


• Vacation time that considers your previous experience  


• Advanced paid hours to recharge your batteries (holidays and mobile days) 


• Flexible benefits plan that adapts to your needs  


• Flexible savings fund option  


• A monthly home internet allowance  

Considerable growth opportunities  

• A career path with opportunities to learn and grow  


• Proximity to your direct manager and open, honest communication to support your development  


• Multiple initial and on-the-job training opportunities and tools to track your progress and help you scale up in your career  

Last but not least: “Sherweblife” - a rich calendar of activities that allow us to gather virtually and face-to-face throughout the year  

At Sherweb, we believe in pay transparency and fairness. The salary range provided is intended to give an indication of what you might expect for this role. However, we recognize that each candidate brings a unique set of skills and experiences. As such, the final compensation package will be tailored to reflect the specific qualifications and expertise of the chosen candidate, ensuring that we remain competitive and equitable in our offerings.  

Reasons for the requirement of English: Sherweb has international customers and fluency in English is the only way to ensure proper service delivery to them. The main tasks related to this position require written and oral communication with an English-speaking clientele at all times.

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