Posted last month
Development Manager — Maintenance & Delivery
@ Windward Software Systems Inc
Penticton, British Columbia
Overview
Windward Software, a Volaris Group business unit within Constellation Software, is hiring a Development Manager to own maintenance and release of its production software and lead a six-developer team. The role is full-time, remote within Canada, and reports to the Head of AI Enablement, Product and Technology. The posting asks for 3+ years leading a delivery team and experience with established products.
Responsibilities:
- Own maintenance, defects, releases and customer commitments for production products
- Lead and manage six developers, including planning and performance
- Set technical standards and make tooling and platform decisions
- Apply and coach AI use across the team
- Own reporting, budget input and team performance measures
Requirements summary:
- 3+ years in technical lead or engineering management
- Software and data technical fluency
- Experience maintaining legacy or established products
- Database and client-server or desktop application experience
- Strong planning, reporting and follow-through
- Interest in AI in engineering
Tools & skills
Source and dates
Employer career site / ATS feed · workday
- Employer posting date
- 2026-09-22
- First seen by our source
- 2026-10-08
- Source record updated
- 2026-10-29
These dates describe the source record, not a live verification that the employer is still hiring. Check the original posting.
Job details
| Seniority | Manager |
| Department | Software development |
| Management experience | 3+ years |
| Manages people | Yes |
| Hours per week | 40 (estimated) |
| Travel | air: none · ground: none |
| Work setting | Home |
| Position | Mostly sitting |
| Physical demands | physical low · computer high |
| Languages | English |
Summary and details written by AI from the posting; the employer’s posting is the authority.
Windward Software Systems Inc
Saved company profile
Historical company information from a saved The Jobs API profile (LinkedIn/Crunchbase fields). It is not live-verified; figures may have changed. Missing values remain unknown.
NOW HIRING REMOTE | Invoicing and inventory control solutions for businesses just like yours.
Full company description
Integrated Point of Sale, Inventory Control, CRM and Accounting Software for your industry- Configured for your unique business. Founded in 1984, Windward Software is a multinational company with 1000's of customers across North America and Australia! Our flagship software, Windward System Five on Cloud is a fully integrated business management solution designed for independent retail and wholesale businesses. Feature rich, scalable, and customizable to the needs of the customer make our solution a must-have for businesses that want to reduce errors, save valuable time, and deliver business results and profitability. Customers appreciate our live international 24/7 support and informative workshops and training sessions offered by our knowledgeable staff. We are proud of our people, our product and of our accomplishments. Servicing Home Goods, Building Materials, and Rental businesses, Windward Software maintains an A+ BBB rating and that over 10,000 Windward stations are in operation worldwide processing over $1.5 Billion in sales. Whether you sell, service, or rent product, Windward Software’s fully integrated business management solution is designed and developed with your specific needs in mind. We help you run your business, instead of just reporting on it! Windward Software is a part of the Volaris Group, an operating group of Constellation Software Inc. (TSX:CSU).
- LinkedIn followers
- 2,773
- People associated on LinkedIn
- 66
- Reported office locations
- Penticton, British Columbia V2A 7K2, CA
- North America, US
- Australia, AU
- Business categories
- Business Development
- Computer
- Software
- Other recorded names
- Windward Software
- Windward Software Systems Inc.
- Specialties
- Point of Sale
- Inventory Control
- Integrated Accounting
- Third Party Integrations
- Custom Development
- 24/7 support
- Mult-store POS
- Customer Management
- Barcoding
- Serial Number Tracking
- Business Intelligence
- Purchasing
- Invoicing
- Rental Management
- Retail POS
- Unit Tracking
- Cloud Platform
- Industry Specific Features
- CRM
- and Professional Services
- Profile identifies a recruitment agency
- No
- Reported total investment
- 0
Currency and observation date were not supplied; this is not a current valuation or a funding round.
Integrated Point of Sale, Inventory Control, CRM and Accounting Software for your industry- Configured for your unique business. Founded in 1984, Windward Software is a multinational company with 1000's of customers across North America and Australia! Our flagship software, Windward System Five on Cloud is a fully integrated business management solution designed for independent retail and wholesale businesses…
| Field | Value |
|---|---|
| Industry | Software Development |
| Company size | 51-200 employees |
| Headquarters | Penticton, British Columbia |
| Organization type | Public Company |
| Year founded | 1984 |
| Specialties | Point of SaleInventory ControlIntegrated AccountingThird Party IntegrationsCustom Development24/7 supportMult-store POSCustomer ManagementBarcodingSerial Number Tracking |
| Open jobs on Jobsy | 1 |
| View page |
Job Summary:
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.
Worker Type:
RegularNumber of Openings Available:
1Journal
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