WHO ARE WE?
Oliver is a technology company focused on simplifying and modernizing the insurance, benefits, and pension administration ecosystem. The Oliver Software Suite is a modern, scalable, and highly configurable platform designed to optimize the distribution and administration of benefits and pension plans across North America.
Our platform supports a wide range of users, including plan sponsors, participants, administrators, adjudicators, underwriters, consultants, unions, employers, third-party administrators, MGAs, insurance carriers, and pension organizations.
We build technology around real workflows and real people. Our solutions help clients modernize complex legacy environments, reduce administrative friction, improve accuracy, connect fragmented systems, and create better digital experiences for everyone involved.
As we continue to scale our platform, modernize our technology environment, and expand our product capabilities, we are looking for a technology leader who can help us make strong technical decisions, improve how we build and deliver software, and create an environment where talented people can do their best work.
YOUR ROLE
As the Director of Technology, you will provide hands-on technical leadership across Oliver’s products, engineering teams, integrations, infrastructure, security, privacy, and broader technology environment.
This is a player-coach leadership role for someone who can think strategically, make sound architectural decisions, support teams through difficult technical problems, and step into the details when needed. It is not a purely administrative or high-level strategy role. You will remain close enough to the technology to understand what is being built, challenge assumptions, identify risks, and help unblock the team.
You will sit at the intersection of Technology, Product, Delivery, Implementation, and Client Success. You will work closely with leaders and teams across the business to turn product ideas, customer requirements, and operational needs into scalable, secure, maintainable solutions that Oliver can confidently deliver and support.
Oliver operates in an increasingly AI-enabled technology environment. We are looking for someone who sees AI, automation, and emerging technologies as practical tools for improving engineering productivity, software quality, testing, documentation, operations, and decision-making - while maintaining appropriate security, privacy, intellectual property, and governance controls.
Above all, we are looking for a curious, collaborative, low-ego problem solver. Someone who asks good questions, communicates openly, surfaces risks early, takes ownership of outcomes, and brings people together to solve problems rather than allowing those problems to move between teams.
YOUR IMPACT
Technology Leadership & Architecture
- Provide technical leadership across software architecture, engineering, APIs, integrations, data, cloud infrastructure, security, privacy, DevOps, and technical operations.
- Help establish and evolve the technical direction and architecture for Oliver’s products and platforms.
- Partner closely with Product to translate business problems, client needs, and product requirements into practical and scalable technical solutions.
- Make and facilitate architectural decisions that appropriately balance speed, scalability, security, maintainability, user experience, and business priorities.
- Promote modular, reusable, configurable approaches that reduce duplication and make future product development and client implementation faster.
Engineering, Delivery & Operational Excellence
- Improve the speed, quality, and predictability of software development, product releases, and client implementations.
- Help teams break complex problems into practical, achievable technical solutions without losing sight of the broader platform architecture.
- Strengthen software engineering practices across design, development, code review, testing, deployment, monitoring, troubleshooting, and production support.
- Promote clear ownership, realistic commitments, measurable progress, and proactive communication across technical work.
- Support effective incident response and root-cause analysis, with an emphasis on learning from issues and preventing repeat failures.
- Create reusable approaches, standards, and technical patterns so that each implementation, integration, and engineering challenge makes the next one easier.
AI-Enabled Engineering & Automation
- Help Oliver continue developing an AI-enabled engineering organization that uses AI thoughtfully to create meaningful leverage.
- Identify practical opportunities to use AI throughout the software development lifecycle, including discovery, requirements, solution design, coding, testing, documentation, debugging, deployment, and operations.
- Encourage experimentation with AI and emerging tools while maintaining appropriate controls around customer data, intellectual property, privacy, security, and vendor risk.
- Establish practical guidance for responsible use of AI-assisted development tools and AI-enabled product capabilities.
- Promote automation of repetitive engineering and operational activities where automation can improve reliability, consistency, or speed.
Security, Privacy & Technical Governance
- Embed security and privacy by design into architecture, products, development practices, integrations, AI capabilities, and infrastructure.
- Help establish practical standards for secure software development, access management, data handling, secrets management, vulnerability management, logging, monitoring, and environment controls.
- Partner with leadership and appropriate internal or external specialists on privacy, cybersecurity, compliance, risk, business continuity, and technology governance.
- Ensure technical risks are understood, documented, communicated, prioritized, and addressed based on business impact.
- Help ensure technology decisions protect Oliver, our customers, and the sensitive information entrusted to our systems.
Integrations, Infrastructure & Platform Reliability
- Guide API and integration strategy for customers, carriers, administrators, partners, data providers, and third-party platforms.
- Develop repeatable integration patterns and standards that reduce one-off solutions and accelerate onboarding of new clients and partners.
- Work with technical teams to support scalable, resilient, observable, and secure production environments.
- Help define expectations for monitoring, alerting, performance, availability, backup, recovery, and operational readiness.
- Support modernization of legacy technology while managing transition risk and maintaining continuity for existing customers.
Leadership, Culture & Collaboration
- Build strong, trusted relationships across Engineering, Product, QA, Implementation, Operations, Client Success, and senior leadership.
- Lead with curiosity and technical judgment rather than ego or hierarchy. Create space for good ideas to come from anywhere on the team.
- Create an environment where risks, blockers, mistakes, and disagreements can be surfaced early and discussed constructively.
- Communicate progress, risks, dependencies, and technical trade-offs clearly to both technical and non-technical stakeholders.
- Take ownership when something is not working and help the organization move from identifying the problem to solving it.
- Coach and mentor technical team members, strengthen engineering capability, and create clear expectations around quality, accountability, and collaboration.
- Model a proactive, dependable, and no-surprises leadership style: communicate early, follow through on commitments, and ask for help before issues become crises.
WHAT TO EXPECT IN YOUR FIRST 90 DAYS
In your first three months, you will:
- Build a strong understanding of Oliver’s products, architecture, data model, integrations, infrastructure, development practices, security environment, and active client commitments.
- Develop strong working relationships with Engineering, Product, QA, Implementation, Operations, and senior leadership.
- Review the current technology architecture and identify the most important technical risks, dependencies, bottlenecks, and modernization opportunities.
- Understand how work moves from product requirements through engineering, QA, deployment, implementation, and production support, and identify practical opportunities to improve that flow.
- Take ownership of one or more meaningful technical priorities and help move them from ambiguity toward a clear plan and measurable progress.
- Assess current AI-enabled development practices and identify opportunities to improve productivity, quality, governance, and cost effectiveness.
- Become a trusted technical leader who teams can rely on for sound judgment, practical problem-solving, clear communication, and follow-through.
THIS IS YOU
Experience
- 10+ years of progressive experience in software development, software engineering, architecture, or technology leadership, with meaningful responsibility for complex production systems.
- Experience leading or providing senior technical direction to engineering teams in a SaaS, software product, enterprise technology, or similarly complex environment.
- A strong hands-on technical foundation. You do not need to be the primary developer, but you must be able to understand architecture, review technical approaches, ask detailed questions, and contribute credibly to difficult technical discussions.
- Demonstrated experience designing, modernizing, or operating scalable applications, platforms, APIs, integrations, and cloud-based systems.
- Experience partnering closely with Product Management and translating product and business requirements into sound technical approaches.
- Experience supporting client implementations, production environments, integrations, migrations, or other delivery work where technical decisions directly affect customers.
Technical Knowledge & Skills
- Strong understanding of modern software architecture, distributed systems, APIs, integration patterns, data architecture, and enterprise application development.
- Strong understanding of cloud infrastructure, environments, deployment practices, observability, monitoring, scalability, reliability, and cost management.
- Strong knowledge of secure software development practices, identity and access management, data protection, application security, and privacy-by-design principles.
- Experience with modern software delivery practices including source control, CI/CD, automated testing, code review, release management, and production support.
- Experience with data integrations, file-based exchanges, APIs, event-driven approaches, background processing, and complex business workflows.
- Practical experience with AI-assisted software development, AI services, automation tools, or AI-enabled engineering workflows.
- Ability to understand complex business rules and translate them into durable technical structures, configurable systems, and maintainable solutions.
Leadership Skills & Attributes
- Curious and naturally inclined to understand the real problem before jumping to a solution.
- Low-ego and collaborative, with the confidence to challenge ideas respectfully and the maturity to change direction when better information emerges.
- Highly accountable and comfortable taking ownership of outcomes that cross team or departmental boundaries.
- Proactive communicator who surfaces risks, blockers, and uncertainty early rather than allowing surprises to accumulate.
- Pragmatic decision-maker who knows when to go deep, when to simplify, and how to balance speed with quality and long-term maintainability.
- Comfortable operating in ambiguity and capable of creating clarity, priorities, and practical next steps without waiting for perfect information.
- Clear communicator who can explain technical issues, options, and trade-offs to engineers, product leaders, clients, and executives.
STRONG ASSETS
The following are not required, but would be considered strong advantages:
- Experience working in insurance technology, Canadian group benefits, health and welfare benefits, pension administration, third-party administration, union benefits, multi-employer plans, or trust fund administration.
- Understanding of eligibility, enrolment, contributions, remittance, billing, premium calculation, claims, member administration, employer administration, plan rules, or benefit administration workflows.
- Experience modernizing legacy enterprise applications or guiding phased migrations from legacy systems to modern platforms.
- Experience in regulated, privacy-sensitive, or data-intensive environments with strong audit, security, or compliance expectations.
- Experience with SOC 2, security assessments, privacy programs, disaster recovery, business continuity, or formal technology risk management.
YOUR SUPERPOWERS
Technical Judgment: You separate what is important from what is merely complicated and help teams make sound technical decisions.
Player-Coach Leadership: You set direction and lead people while staying close enough to the work to help when the team needs you.
Systems Thinking: You understand how architecture, data, integrations, security, infrastructure, product decisions, and implementation realities affect one another.
Practical Problem-Solving: You ask good questions, work through ambiguity, and move problems toward clear, achievable solutions.
Low-Ego Collaboration: You listen, challenge respectfully, invite expertise from others, and care more about the outcome than whose idea wins.
Ownership & Follow-Through: You surface issues early, communicate clearly, follow through on commitments, and stay with important problems until they are resolved.
CERTIFICATIONS AND EDUCATION
- Bachelor’s degree in Computer Science, Software Engineering, Information Systems, or equivalent practical experience.
- We value demonstrated technical judgment, leadership capability, continuous learning, and practical experience as much as formal credentials.
YOUR COMPENSATION & BENEFITS
At the time of this posting, the estimated annual base salary for this position is $140,000-$165,000. Individual compensation within this range is determined by factors such as job-related skills, relevant experience, and education/training. This range reflects the annual base salary only and does not encompass the comprehensive total rewards package that we proudly offer.
Perks & Benefits:
- Flexible remote work options with occasional on-site collaboration.
- Comprehensive medical, dental, vision, and mental health programs.
- Professional development support, including training, certifications, and leadership development.
- Generous vacation, sick days, and personal leave.
- Employer-matching RRSP program.
WHAT YOU’LL GET
At Oliver, our purpose is to empower success, propel evolution, and ignite innovation for the future. Our culture is built on:
- Integrity & Care
- Simplicity
- Continuous Learning & Growth
- Design Success
You will play a central role in shaping the next generation of Oliver’s technology organization and platform. Your decisions will directly influence how we build products, protect customer data, deliver implementations, modernize legacy technology, and scale our capabilities across the benefits and pension ecosystem.
This is a role for someone who wants meaningful ownership, enjoys solving difficult problems with good people, and believes strong technology leadership is equal parts technical judgment, curiosity, accountability, collaboration, and execution.
10+ years in software development, engineering, architecture, or technology leadership; hands-on experience with production systems, cloud platforms, APIs, integrations, security, and software delivery; bachelor's degree or equivalent experience.
Key Responsibilities
- providing leadership
- guiding architecture
- coaching teams
Skills & Tools
APIs, CI/CD, AI, Microsoft
Job Details
- Category: Information Technology
- Seniority: Senior Level
- Commitment: Full Time
- Workplace: Remote — British Columbia, Canada
- Salary: CAD 140,000 – 165,000 / year
- Languages: English
Benefits
- Generous paid time off
- Tuition reimbursement
- Retirement plan
About Oliver
A technology company that modernizes insurance, benefits, and pension administration through scalable software platforms. — Industry: Information Technology