[Hiring] Head of Delivery @Vesta Software Group

Role Description

The Head of Delivery is responsible for leading all aspects of development delivery across JMS. This position ensures that custom development projects, product enhancements, and defect fixes deliver revenue and are delivered on time, to specification, and to a consistently high quality.

This is a commercially accountable role responsible for delivering Professional Services revenue through customer-funded custom development. The Head of Delivery ensures that all paid-for development work is delivered profitably, to committed customer deadlines, and in line with contractual expectations.

This role owns the PS development forecast, ensures delivery capacity is aligned to commercial demand, and is accountable for hitting revenue and margin targets.

Qualifications

• Experience in leading software development teams.
• Strong understanding of ERP systems and the metals industry.
• Proven track record in managing customer-funded development projects.
• Excellent communication and leadership skills.

Requirements

• Own the commercial performance of all customer-funded development work, including revenue, margin, and delivery against the PS business plan.
• Ensure all custom development is delivered on time to contractual deadlines, protecting revenue recognition and customer satisfaction.
• Maintain accurate rolling revenue forecasts for custom development and ensure delivery capacity matches commercial demand.
• Collaborate with Finance to ensure proper revenue recognition, invoicing triggers, and margin tracking.
• Define and enforce commercial rules of engagement for scoping, estimating, and approving custom work.
• Lead all day-to-day software development delivery activities across JMS’s product lines.
• Ensure predictable, high-quality delivery of customer-funded custom development, core product enhancements, and defect fixes.
• Forecast and custom development revenue and deliver against forecast.
• Operate strictly within the architectural patterns, guardrails, and design principles defined by the Head of Architecture & AI.
• Establish and enforce delivery governance, ensuring consistency, transparency, and alignment with the product roadmap.
• Own the functional product roadmap, supported by the Product Manager.
• Translate product strategy into estimated, planned, and sequenced delivery commitments.
• Ensure roadmap items are feasible within existing architectural constraints and timelines validated with Architecture & AI.
• Act as the commercial owner of all custom development commitments, ensuring profitability, feasibility, and alignment with revenue targets.
• Ensure customer deadlines are met consistently, as delays directly impact revenue recognition and customer satisfaction.
• Approve all estimates and delivery commitments with commercial viability as the primary decision factor.
• Collaborate with the Professional Services Manager to confirm resource availability and capacity for project-driven development.
• Own backlog management across enhancement, maintenance, custom development, and technical debt items.
• Plan and run sprint ceremonies including backlog refinement, sprint planning, and retrospectives.
• Maintain a reliable release cadence and continuously improve forecasting accuracy.
• Lead the QA function, ensuring all development work meets agreed quality standards before release.
• Oversee functional testing, regression testing, UAT support, and test cycle planning.
• Ensure clear acceptance criteria, repeatable test processes, and strong defect prevention controls.
• Ensure completed work is packaged, tested, documented, and ready for installation by Platform Engineering.
• Prepare release notes, user documentation inputs, and internal communication for upcoming releases.
• Collaborate with Platform Engineering to ensure delivery outputs conform to deployment and installation requirements.
• Lead, coach, and develop cross-functional development and QA teams (onshore and offshore).
• Establish and maintain consistent delivery workflows and engineering practices across teams.
• Collaborate with the Head of Architecture & AI on design feasibility, architectural impacts, and development approaches.
• Partner with Platform Engineering to align environment needs, CI/CD integration points, and deployment readiness.
• Work closely with the Product Manager on roadmap prioritisation, requirements clarity, and customer value alignment.
• Support the Professional Services Manager with development dependencies for implementations and migrations.
• Work with the Customer Support Manager to prioritise customer-reported defects and ensure timely remediation.
• Support the Enterprise Account Manager with technical insight for major customer escalations and roadmap visibility.
• Contribute to the strategy and future direction of the company through active participation in monthly Senior Leadership Team meetings.
• Foster strong relationships with other Senior Leadership Team members, maintaining regular communication to ensure mutual awareness of activities, issues, and priorities.
• Act as an ambassador for the company at Jonas Group and industry events.
• Set an appropriate example for other members of staff in terms of conduct, ethics, and embodiment of company values.

Benefits

• Competitive salary.
• Comprehensive health benefits.
• Opportunities for professional development.
• Flexible working hours.

Company Description

Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services, to name a few. Within these markets, Jonas is comprised of over 65 distinct brands, each a respected leader in its domain.

Jonas’ vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of “Software for Life.” We are committed to technology, product innovation, quality, and exceptional customer service.

Jonas Software supports over 60,000 customers in more than 30 countries. We employ over 6,000 skilled professionals, including industry experts and technology specialists. Across our broader network, we support a global workforce of more than 30,000 employees.

Headquartered in Canada, Jonas Software has a global footprint with offices around the world. We’re a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index.