Development Manager - Maintenance & Delivery

Windward Software is seeking a Development Manager to own the maintenance and release of our production software and to lead the team that sustains it. Reporting to the Head of AI Enablement, Product and Technology, you will manage six developers directly, with quality assurance reporting through its own lead. You will be accountable for defect resolution, releases and customer commitments across all products in production, and for the technology decisions that keep the installed base supportable. This is a remote role based in Canada.
Job Description
The role
Thousands of business users open Windward software when they open their doors. This role keeps it working, and takes ownership of everything we build next.
Own the software Windward has in the field today, and everything we release from here. You are accountable for its health, supportability and release, and you lead the development team that sustains it.
You manage six developers directly. Quality assurance reports to you through its own lead.
About Windward
Windward Software is a Volaris Group business unit within Constellation Software Inc. We build business management and ERP software, including System Five, that helps independent retailers, wholesalers and service businesses run their entire operation. We are developing new software while continuing to support the customers who run their business on our established products today. Both halves of that matter, and this role holds one of them.
What you will do
Sustain the products in the field
Own maintenance, defect resolution, releases, patches and customer commitments across all products in production, current and future.
Make the technology decisions for the products you manage: tooling, platform and upgrade choices, within organization-wide technology and AI standards.
Set the bar a new product meets before it transitions to maintenance: documentation, test coverage, operational readiness and support training.
Own the maintenance of the installed base: version currency, upgrade paths and the technical debt position of released software.
Lead the development team day to day
Run delivery for six developers: cadence, prioritization, sprint planning, unblocking and the schedule the team is held to.
Grow the team, and own performance, development, capacity and hiring input.
Own quality assurance outcomes, held through the quality assurance lead who manages that team.
Approve concepts, approaches and direction for maintenance work, and hold technical standards consistent across the team's output.
Own the administration of the function: reporting, the performance review and scorecard cycle, budget input, and the team's performance measures.
Put AI to work across the team
Apply the organization's AI standards and tooling to the team's daily work.
Coach the team to design, build, test and ship with AI, and build the capability to use it well.
Partner across the organization
Work closely with product management, technical architecture, cloud operations and IT, and customer support.
What you will bring
3+ years in a technical lead or engineering management capacity leading a delivery team.
Technical fluency in software and data: deep enough to approve concepts, assess approaches and hold a standard.
Experience maintaining and evolving an established or legacy product while introducing new technology and practices.
Strong planning, reporting and follow through, treated as a core part of the job.
Real enthusiasm for AI in engineering, and the judgement to know where it applies.
Solid software architecture and delivery fundamentals; database and client-server or desktop application experience.
A clear communicator and mentor who keeps a small team focused, productive and motivated.
Nice to have:
System Five, ERP or business management software domain experience; database platform migration, including Btrieve or Actian Pervasive to PostgreSQL; cloud and SaaS modernisation; coordinating remote teams of development and QA resources.
Why this role
Everything Windward sells today, and everything it releases from here, sits under this role. You get a defined team, full accountability for the installed base, and the authority to set the technical standard maintained software meets. It is a rare amount of ownership for a team this size, with the backing of the Volaris and Constellation model behind it.

Work arrangement
Yes