Director of Engineering

Aspire Software

. Manage, coach, and develop engineers through regular 1:1s, clear expectations, and consistent feedback .

Posted 10/20/2026full-timeRemote • Canada, United StatesLead💰 CA$170,000 - CA$200,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in managing engineering teams, driving software development lifecycles, and implementing agile practices. Proficient in Java, Azure, and compliance frameworks, with a strong focus on optimizing performance and ensuring release quality.

Highest-signal resume keywords

Java Back-End DevelopmentAgile Practices ImplementationCI/CD and Test AutomationSite Reliability EngineeringPCI DSS Compliance

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Software DevelopmentRelational Database DesignPerformance OptimizationIncident ManagementTechnical Direction SettingCode Review StandardsAutomated TestingERP ModernizationCloud OptimizationLegacy System Support

Soft Skills

Coaching and DevelopmentCommunication SkillsTalent AssessmentFeedback DeliveryTeam Leadership

Tools & Technologies

AzureJavaLinuxPerlSpring BootOracleSQLAI-Assisted Development ToolsCI/CD ToolsAutomated Testing Tools

Industry Keywords

B2B SystemsDistribution SoftwareSupply Chain SoftwarePrint IndustryPromotional Products Industry

Tech Stack

Tools & technologies

AWSAzureCloudERPGoogle Cloud PlatformJavaLinuxOraclePerlSpringSpring BootSpringBootSQL

About the role

Key responsibilities & impact

Manage, coach, and develop engineers through regular 1:1s, clear expectations, and consistent feedback
Assess team strengths and gaps and recommend hiring, development, and organizational structure
Hire and onboard engineers and build a culture of ownership, accountability, and continuous improvement
Set technical direction and lead architecture decisions for the next-generation ERP, including finalizing the Java-based technology stack
Conduct code reviews, design, prototype, and contribute directly to critical components
Balance modernization with support for existing product lines and customers and proactively manage technical debt
Own the software development lifecycle, including sprint cadence, daily standups, retrospectives, and release schedules
Strengthen automated testing, CI/CD, and Engineering ownership of release quality
Set standards for code review, testing, and observability
Drive adoption of AI-assisted development tools such as Claude Code, Cursor, and Copilot
Provide technical feasibility input and sizing estimates during epic kickoffs and discovery
Own quarterly and sprint engineering capacity planning
Communicate trade-offs, risks, and progress to Product, Support, and leadership
Oversee IT/Infrastructure and Site Reliability Engineering alongside software engineering
Own production incidents and the on-call model and serve as escalation point for outages and critical issues
Own the PCI compliance process from controls and audits through remediation
Optimize Azure costs by tracking spend and right-sizing environments
Keep the legacy Linux, Perl, Spring Boot, Oracle, and SQL platform stable and secure

Requirements

What you’ll need

8+ years in software development, including 3+ years managing engineering teams
Strong hands-on Java experience in back-end and enterprise applications
Experience building or modernizing an ERP or complex transactional B2B systems
Track record implementing agile practices, CI/CD, and test automation
Strong relational database design and performance optimization skills
Ability to assess talent, give direct feedback, and make tough people decisions
Hands-on Azure experience, including managing and optimizing cloud spend; AWS or GCP also considered
Experience building or leading a QA function and test automation strategy
Experience owning production operations, on-call rotations, incident management, and Site Reliability Engineering practices
Experience with PCI DSS compliance or a comparable security and compliance framework in a production environment
Comfort supporting and modernizing legacy systems, including Linux, Perl, Spring Boot, Oracle, and SQL
Active, hands-on use of AI-assisted development tools
Excellent communication skills and ability to translate technical issues into business impact
Experience in distribution or supply chain software, or the print and promotional products industry (strongly preferred)
Experience in an acquisitive, growth-stage vertical software business (strongly preferred)
Experience managing teams distributed across Canada and the U.S. (strongly preferred)

Benefits

Comp & perks

AI-powered tools, including transcription and automated note-taking, used during portions of the interview process
Alternative interview-process accommodation available upon request
Commitment to diverse, equitable, and inclusive teams