Vice President, Technology

WHO ARE WE?

Oliver is a technology company built on clarity, connection, and care. We design solutions that make the insurance and benefits ecosystem work together with greater confidence, simplicity, and ease. Our platform ecosystem bridges legacy and modern environments helping insurers, TPAs, advisors, and pension organizations modernize without disruption.

What sets us apart is our deep operational understanding of how the industry truly works. We build technology around real workflows and real people, not theoretical models. Our tools integrate the systems others struggle to connect, reduce administrative friction, and create measurable improvements in accuracy, transparency, and user experience.

Our culture is grounded in honesty, collaboration, and craftsmanship. We listen first, communicate plainly, and focus on delivering solutions that genuinely help people do their best work. Internally, we are curious, thoughtful, and united by a shared purpose: to bring clarity to complexity and make modernization feel simple, practical, and human.

As we scale our platform and expand our impact across North America, we are continuing to build a leadership team that reflects these values and drives our next stage of technological evolution.

YOUR ROLE

As Vice President, Technology, you will lead Oliver's engineering, architecture, QA, DevOps, and technical delivery functions the teams responsible for building, scaling, and releasing our platform ecosystem. Reporting directly to the President, working alongside the President, CEO, and Senior Vice President.

You will be responsible for building and scaling the engineering organization, overseeing its teams, functions and overall performance that delivers reliable, secure, and modern technology solutions. This includes full ownership of engineering, QA, DevOps, architecture, technical delivery, and the end-to-end development pipeline from build QA UAT release.

You will partner closely with the business and product teams, ensuring that technical execution aligns with operational needs, client expectations, and company strategy. You bring both technical depth and operational rigor, able to operate at an executive level while also stepping into the details when needed.

This is a pivotal leadership role designed for a builder, someone who not only has experience scaling a technology function, but who thrives in creating structure, systems, and teams from the ground up. This leader is ready to help Oliver elevate, modernize, and expand its technology capabilities. As Oliver grows, this role has a natural runway toward Chief Technology Officer (CTO).

YOUR IMPACT

Technology Leadership & Vision

• Provide executive leadership for all engineering, QA, DevOps, and technical operations teams.
• Establish a cohesive technology vision that supports platform modernization, scalability, and reliability.
• Build a culture of excellence, accountability, continuous learning, and technical craftsmanship.
• Identify and implement the technology strategy needed to support Oliver's growth over the coming years.

Engineering & Delivery Management

• Own the end-to-end development lifecycle and delivery pipeline, ensuring high-quality releases that are ready for business and client use.
• Lead engineering managers and technical leads, supporting them in coaching, hiring, decision-making, and performance management.
• Introduce operational discipline across engineering processes: sprint execution, QA rigor, documentation, release governance, and cross-team alignment.
• Improve predictability, throughput, and transparency across all engineering teams.

Organizational Design, Reporting & Engineering Performance

• Design and scale Oliver's technology organization, aligning roles, responsibilities, structures, and operating mechanisms to support growth.
• Recruit, develop, and retain top-tier engineering talent and leaders.
• Build succession planning and leadership pipelines across the technology division.
• Establish data-driven reporting systems that provide transparent visibility into engineering productivity, capacity, and turnaround times.
• Develop and maintain analytics dashboards that track workflow efficiency, delivery velocity, and organizational health.
• Implement mechanisms for ongoing performance measurement across teams, ensuring leaders have actionable insights to guide decision-making and resource allocation.
• Build a culture of data-informed planning, enabling engineering leaders to forecast needs, identify bottlenecks, and optimize team performance.

Technical Strategy & Architecture Oversight

• Guide architectural direction and platform modernization in partnership with senior technical leaders.
• Ensure engineering teams are delivering scalable, secure, maintainable solutions.
• Lead improvements to platform performance, reliability, and developer productivity.

Cross-Functional Partnership

• Work closely with the Senior Vice President to ensure alignment on priorities, requirements, and readiness.
• Act as the technical point of contact during key client conversations or escalations when needed.
• Support organizational initiatives and enterprise-wide platform enhancements.
• Serve as a strategic advisor to the organization on complex technology challenges, providing guidance on trade-offs, risks, and solution paths.
• Partner with cross-functional leaders to translate business problems into technical strategies and data-informed recommendations.
• Develop frameworks and processes that help the organization evaluate technology choices, architectural decisions, and operational impacts.
• Offer expertise and thought leadership on emerging technologies and industry best practices to inform company-wide decision-making.

Operational Excellence

• Establish KPIs, quality measures, and reporting that create visibility into engineering performance.
• Reduce delivery risk through proactive issue identification, mitigation, and process improvement.
• Ensure technology decisions support both short-term business needs and long-term scalability.
• Create consistent mechanisms for measuring delivery velocity, cycle times, and overall engineering throughput.
• Establish operational playbooks and best practices to ensure predictable, high-quality engineering outcomes.
• Partner with product, design, and operations leaders to optimize cross-functional workflows and eliminate bottlenecks.

WHAT TO EXPECT

In your first three months, you will:

• Gain a deep understanding of Oliver's platform, technology stack, engineering workflows, and current pain points.
• Assess the strengths and gaps within the technology organization and define a plan for team structure, standards, and leadership alignment.
• Establish clear expectations with engineering managers and technical leads.
• Stabilize delivery processes and introduce operational discipline to ensure predictable delivery.
• Quickly become a trusted partner to the President, VP of Business/Operations, and product leadership.
• Take ownership of one or more priority initiatives, such as modernization work, Oliver Connect, or EXL technical support and bring clarity, structure, and momentum.

THIS IS YOU

Experience:

• 15+ years of progressive experience in technology, including at least 10 years in senior leadership roles overseeing engineering teams and managers.
• Proven success in a VP, Head of Engineering, CTO, or similar senior technology leadership role ideally in a startup or scale-up environment.
• Deep experience supporting large enterprise software or SaaS platforms.
• Track record of modernizing technology teams, processes, and systems.

Skills & Attributes:

• Strong technical background in modern software engineering, cloud infrastructure, security, and architecture.
• Exceptional communication skills able to translate between business and technical contexts.
• Highly self-directed, resourceful, and comfortable operating in ambiguity.
• Delivery-focused with an ability to prioritize, sequence, and execute effectively.
• A builder who thrives in environments where they can leave a lasting imprint.

Certifications and Education:

• Bachelor's degree in computer science, Engineering, or equivalent experience.
• MBA or equivalent business education is an asset. Bachelor's degree in Computer Science, Engineering, or equivalent experience.
• Additional leadership or technology certifications are an asset, including Agile, Scrum, PMP, and other program or project management credentials.
• Certifications in delivery and process frameworks—such as Lean, Six Sigma, Kanban, or Agile Coaching—are also highly valuable.
• Certifications in cloud platforms (e.g., AWS, Azure) or architecture and engineering frameworks (e.g., ITIL,) are considered beneficial.

YOUR SUPERPOWERS

• Technology Transformation: You have led modernization initiatives, improved engineering quality, and built scalable systems.
• Operational Excellence: You know how to bring structure, measurement, and predictability to a fast-moving engineering organization.
• Leadership of Leaders: You excel at building, coaching, and empowering high-performing teams and technical managers.
• Startup Execution Mindset: You are hands-on when needed, decisive, and comfortable building structure where none exists.
• Cross-Functional Influence: You partner effectively with product, business, and operations leaders and can represent technology in client-facing conversations.

YOUR COMPENSATION & BENEFITS

At the time of this posting, the estimated annual base salary pay range 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 on-site collaboration when needed
• Comprehensive medical, dental, vision, and mental health programs
• Professional development and leadership coaching support
• Generous vacation 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

As VP of Technology, you will play a defining role in shaping the next generation of Oliver's technology and accelerating our growth across North America. You will help build a technology organization capable of supporting our future scale, and if all goes well you will be on a natural path toward becoming Oliver's future Chief Technology Officer.