Headquarters:

400–15315 31st Ave, Surrey, BC, V3Z 6X2

Year founded:

2014

Number of employees:

Phone:

778 200 5757

Email:

gerald@oliver.app

Website:

oliver.app

LinkedIn:

linkedin.com/company/oliver-software

“We prioritise embracing cutting-edge technologies, creative problem solving and continuous improvement to enhance our premium funding solutions and provide exceptional value to our clients”

Gerald Cole

Chief Executive Officer

Corwyn Amendt

President

Riyaad Ammantoola

Vice President, Market Development and Growth

Leadership

As CEO of Oliver Software, Gerald Cole brings nearly two decades of experience in technology, entrepreneurship, and the group benefits industry. He is known for solving complex operational and industry challenges with practical, scalable solutions rooted in collaboration, focus, and data-driven execution. His leadership emphasizes seamless ecosystem integration, strong partnerships, and measurable impact.

Chief Executive Officer

Gerald Cole

Corwyn Amendt, president of Oliver Insurance Software, is a seasoned technology executive with over 25 years of experience modernizing group benefits administration. He has led major platform transformations and digital innovation across regulated environments. At Oliver, he drives a focused strategy to deliver scalable, user-centric solutions for unions, trust funds, employers, and members. Combining deep industry expertise with strong product vision, Amendt guides teams to improve operations while meeting strict compliance and data-integrity requirements. Known for his collaborative style and commitment to meaningful change, he is a respected leader in benefits technology and organizational transformation.

President

Corwyn Amendt

Riyaad Ammantoola is a transformative leader in the pensions and benefits industry, known for elevating service delivery, operational excellence, and member outcomes. With over 17 years of experience across major institutions in Canada, the US, and Europe, he has led award-winning teams through modernization, digital innovation, and service redesign. As vice president at Oliver, Ammantoola advances a people-first vision for benefits administration, integrating technology, human-centered design, and operational strategy. He holds designations in financial planning, retirement consulting, Lean Six Sigma, and change management, demonstrating his commitment to continuous improvement and exceptional client experience.

Vice President, Market Development and Growth

Riyaad Ammantoola

BRETT BASTOW, IQUMULATE PREMIUM FUNDINGs

Leadership

Ananda Rao Thudi

Senior Technical Strategist and Domain Expert

Rao Thudi is a veteran technology leader with over 30 years of experience advancing solutions in the pension, health, and welfare industry. Beginning his career in the early 1990s with a Master of Computer Applications, he spent several years in India’s software sector before moving to Canada in 1999. Since joining CDAT/Oliver that same year, Rao has been a key contributor to the organization’s evolution. Known for his analytical mindset and strength in functional and technical problem-solving, he brings deep expertise in data migration and a longstanding passion for building and enhancing Oliver’s products and capabilities.

Senior Technical Strategist and Domain Expert

Ananda Rao Thudi

Rob Fuller

Head of School (10-12)

Rob Fuller commenced as head of school (Years 10–12) in 2024. He joined Kingswood College from Ivanhoe Girls’ Grammar School, where he was director of curriculum. He is a passionate teacher of politics, history and English and has held roles such as year level coordinator and curriculum leader across the middle and senior years. He is deeply committed to supporting students through their VCE journey and enhancing teacher practice. At Kingswood, Fuller has introduced improved subject selection processes, reimagined the Student Representative Council and strengthened student-centred initiatives that promote resilience, character and meaningful real-world learning experiences.

Head of School (10-12)

Rob Fuller

Stevens & Associates Lawyers is a leading and trusted employment law firm based in Sydney known for delivering high-quality legal expertise in the area of employment law and industrial relations across Australia, alongside a proven track record of effectively and swiftly resolving a variety of workplace law issues. In the past year, the firm’s growth has been notable. It has: • experienced a 213% growth in the number of client matters, increasing from 149 client matters in the 2022 financial year to 390 client matters in the 2023 financial year • improved its online visibility, leading to over 50 online enquiries each month and a conversion rate of client leads of up to 40% • significantly expanded the breadth and type of matters that it advises on day to day, which has increased the firm’s skillsets, diversity and resilience • expanded its community outreach by collaborating with local Sydney venues for client seminars and continuing active participation in a Sydney small/family business group Stevens & Associates Lawyers has adapted to digital trends by implementing an effective strategy with SEO and web design, resulting in a structural shift that has seen increased representation of employees where the firm previously mainly advised employers. The firm’s recognition as a “Fast Firm” attests to its momentum in the employment law space.

“IQumulate is on a technology journey, and we’re just getting started”

Wayne Tower, IQumulate Premium Funding

Tina Flyger

Head of People and Culture

Matthew Westwood-Hill

Chief Information Security Officer

Kathy Pallasis

Manager, Human Resources

Pam Chhabra

Manager – Residential Strata

Tina Flyger commenced as head of people and culture in 2024. With over 15 years of human resources experience, she believes people are the cornerstone of any organisation. She takes a collaborative approach, working closely with executives, managers and teams to shape and deliver effective strategy. She is a dynamic, approachable and highly experienced people and culture leader, with a background spanning both schools and industry. Flyger’s expertise is key to nurturing staff and students, strengthening relationships, and fostering a positive, forward-looking culture that supports the continued growth and success of the Kingswood College community.

Head of People and Culture

Tina Flyger

Matthew Westwood-Hill is a seasoned cyber security leader with over 20 years’ experience in digital forensics, incident response and information security. He has led teams at SBS, CyberCX, and Ernst & Young, managing major incidents and aligning security strategies with business goals. Westwood-Hill is known for his innovative, risk-reducing solutions and clear communication with executives and regulators. He drives awareness, compliance and resilience through training, policy and strategic planning. A frequent speaker and media contributor, he holds advanced qualifications in cyber security and digital forensics and is a recognised expert witness committed to continuous learning and emerging threat readiness.

Chief Information Security Officer

Matthew Westwood-Hill

Kathy Pallasis, manager, human resources at Frontier Software, leads HR strategy and operations from Melbourne. She oversees policy development, employee relations, and internal communications, working closely with senior leadership and cross-functional teams. Pallasis is known for her clear, responsive communication and collaborative approach. She manages employee records, supports strategic planning and coordinates workplace logistics. With experience in enterprise software, payroll systems and governance, Pallasis is a trusted resource for internal stakeholders. She holds a humanities degree, is a member of AHRI, and actively contributes to continuous improvement and inclusive workplace practices through policy and operational leadership.

Manager, Human Resources

Kathy Pallasis

Stephen McMillan first entered the financial services Industry when he joined GE Capital as a finance analyst in 2008, from which he progressed through roles working both onshore and offshore. From there, he moved into Pacific Premium Funding as a financial planning and analysis leader in 2012 and was a key resource in the evolution of the business, first with the successful sale to Macquarie Pacific Funding and then the following progression into IQumulate Premium Funding, where he is now the commercial manager. As commercial manager, McMillan leads a team that is responsible for commercial analysis and business support, identifying and reporting improvement initiatives, and the securitization and treasury functions of the business.

Commercial Manager

Stephen McMillan

One culmination of these efforts has been the real-world, needs-based IQEdge solution. A one-stop online quoting tool designed for both the Australian and New Zealand markets, IQEdge delivers quotes in under 60 seconds. Plus, the solution offers quote comparison and quote versioning capabilities, enabling users to review vital historical and financial data in a single page view. IQEdge can streamline and automate application processing, underwriting document verification and payment collection, cutting the need for manual labour and minimising processing errors. A digital “self-service” platform, IQEdge, reduces the need for customer and administrative support. Meanwhile, borrowers can access their accounts, make payments and manage their policies independently and through sales and support teams, which are always available for further assistance. “We’ve created a quality platform that simplifies the quoting process yet amplifies the customer experience,” says Gordon. “It’s a real game changer.” IQumulate offers an online digital quoting tool to clients. The best-in-market solution enables IQumulate to tailor funding offerings to brokers that align with their prefered distribution channel.

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What does IQumulate have in mind for the future? “IQumulate is on a technology journey, and we’re just getting started,” says Wayne Tower, CEO. “Through continuous engagement with our clients, partners, marketplace and industry, we will listen to the needs as they arise and position our business to be agile and respond to changes as they occur. “Faster decision-making innovations such as AI-powered decision support systems can expedite the underwriting and approval process, leading to quicker responses to clients. This can improve client satisfaction and potentially attract more business, creating a competitive advantage with the potential to allow IQumulate to command premium pricing or capture a larger market share. “As forward-thinkers with a digital and ‘do it better’ mindset, we collectively and proactively look to learn and improve on our customer experience for our clients, paving the way for successful business outcomes for our clients and our business in the coming years ahead. “We’re excited for the future and look forward to what’s on the horizon.”

Adam Basaldella

Manager – Claims

Product Manager

Claire Watson

Commercial Manager

Stephen McMillan

Claire Watson

Product Manager

Claire Watson

Product Manager

Claire Watson

“Our teams measure value through clarity, reliability, and real improvements in accuracy, compliance, and experience”

Gerald Cole, Oliver Insurance Software

“We unify the people, systems, and processes that power insurance and benefits, offering a flexible platform ecosystem that bridges legacy and modern environments without ‘rip and replace’”

Gerald Cole, Oliver Insurance Software

Ivan Verescuk

Chief Executive Officer and Managing Director

Shaun O’Brien

Head of Underwriting

Emily Walker

Head of Strata and Development

Rex Oakman

Head of Operations and Risk

Sandy Newton

Head of Underwriting

Andrew Mitchell

Manager – NSW

Michael Prokopis

Manager – Southern Region

Pam Chhabra

Manager – Residential Strata

Jeffrey Valdivia

Manager – Commercial Strata

Adam Basaldella

Manager – Claims

Many insurers and benefits organizations face a familiar hurdle when they try to update legacy systems. Oliver Insurance Software has earned accolades by making that work feel manageable. Its platform brings people, data, and operations into one environment in a way that matches how the industry actually runs. That approach has earned the company a 5-Star Technology Provider award for 2025 from BPM. Oliver describes its culture as straightforward and collaborative. Teams are encouraged to be curious, thoughtful, and work with purpose. Much of the company’s judgment comes from long experience in benefits and insurance, supported by a habit of looking for practical fixes that help organizations move through complexity without turning everything upside down. Those instincts carry into product development and client delivery. CEO Gerald Cole guides the overall direction with an emphasis on user needs, integrations that matter, and outcomes clients can trust. President Corwyn Amendt manages execution and the day-to-day evolution of the platform. Vice president Riyaad Ammantoola brings a delivery background shaped by pensions, service design, and analytics. Senior technical strategist Rao Thudi adds the deep system knowledge that helps keep the technology dependable and consistent.

IQumulate invests in education and people, which are vital to attracting new business and talent to the company. “We have long tenures for several of our key staff, including some in leadership positions, and this sound working knowledge of our business, practices and industry provides great insights and a wealth of experience to offer our clients,” says Bastow. “Our new head of sales, Graeme Gordon, formerly manager for New Zealand, joins us in Australia to drive our sales strategy and lead our team to successful outcomes for our clients and our business. We look forward to great things ahead with Graeme as he continues to be active and present in the New Zealand market as well as building sound working relationships and new connections in Australia.” Clients can also expect a lot from working with IQumulate. “Through active engagement with our trusted broker network, IQumulate provides relevant information, education and training content,” says Graeme Gordon, head of sales. “Our clients can expect IQumulate to support their business in several ways, providing an understanding of what premium funding solutions are available and how IQumulate can spread the cost of insurance and help borrowers get the right level of insurance cover to free up their cash flow for other expenses or business growth opportunities. Premium funding is often considered a tool for those who simply cannot afford to pay their premiums in full. While this is certainly a significant driver for many, it is also successfully used by profitable companies who use premium funding to manage their cash flows more wisely or better manage their liquidity.”

Medal

Recruitment Solutions Software

Benefits

Compensation

Culture

Diversity, equity and inclusion

Innovation

Reputation

Sustainable programs

Overall

Oliver’s edge lies in how it approaches connection. The company avoids big rebuilds unless they are necessary. Instead, it works to bring systems together in a way that reflects the actual pace of operations. “Oliver stands out because we focus on connection, not disruption,” says spokesperson name and title. “We unify the people, systems, and processes that power insurance and benefits, offering a flexible platform ecosystem that bridges legacy and modern environments without ‘rip and replace.’” Clients tend to notice this early in the relationship. The team spends significant time on integration design, data mapping, and workflow reviews that reduce risk and help teams trust the system from day one. Over the past couple of years, the team has put much of its energy into tightening the nuts and bolts of the platform. Work on Oliver Connect and the Unified API Platform has helped clients get up and running with fewer bumps and has made day-to-day system interactions smoother. Work on group billing, multi-plan administration, and consulting has made it easier for organizations to adopt new tools without unnecessary cost or disruption. This strategic focus enables clients to adopt modern tools with confidence, linking systems, improving accuracy, and delivering better experiences for members, employees, and retirees. Clients often arrive with specific operational issues. Oliver responds by keeping the path straightforward. Onboarding follows a clear structure, with data migration and validation handled in steady steps. Integrations are added only when needed, which keeps projects contained and reduces the risk that accompanies replacing older systems. Many clients report smoother workflows, fewer errors, and more consistent experiences for members and employers. “Our teams measure value through clarity, reliability, and real improvements in accuracy, compliance, and experience,” adds spokesperson. The company’s roadmap builds on this foundation. Plans include expanded real-time capabilities in Oliver Connect, stronger API infrastructure, and more support for pensions, hour banks, and multi-employer plans. Consulting services and selective AI features are also in development, aimed at reducing administrative work.

Re-engineering insurance and benefits for how the world actually works For decades, insurance and benefits organizations have been sold a false choice: live with legacy systems that no longer fit the business, or endure risky, expensive transformations that disrupt everything in the name of modernization. That framing is outdated. At Oliver Insurance Software, we believe there’s a better path, one that applies modern architecture, platform thinking, and data discipline to the real constraints of insurance and benefits operations. Not to blow them up, but to make them finally work the way they should. That perspective is why Oliver was named a 2025 5-Star Technology Provider by BPM, and why a growing number of insurers, TPAs, administrators, and plan sponsors are choosing a fundamentally different model for modernization. Innovation that respects reality The insurance and benefits industry isn’t short on software. What it lacks is software that understands how fragmented, regulated, and interconnected the ecosystem actually is. Oliver was built around a simple belief: modern platforms should adapt to the business, not force the business to adapt to them. Instead of “rip and replace” programs that stall under their own weight, Oliver delivers an integration-first platform ecosystem that connects legacy systems, modern tools, and third-party partners through a unified operational layer. Progress happens faster. Risk stays contained. The business keeps running. This is innovation with intent: APIs designed for real operational workflows data models purpose-built for insurance and benefits modular capabilities that scale as complexity grows Modernization becomes continuous, not episodic. Integration is the product At the center of the platform is Oliver Connect, a unified API and integration framework built specifically for insurance and benefits. It brings policy, billing, eligibility, pensions, hour banks, group administration, and external partners into a single, coherent operating model. When systems actually talk to each other, everything changes: manual workarounds disappear data becomes trustworthy new plans and partners onboard faster members, employers, and administrators get better experiences Clients don’t experience Oliver as “another system.” They experience it as clarity.

Operators, not tourists Oliver is led by people who’ve lived inside the systems they’re building. CEO Gerald Cole sets the vision around usability, integration depth, and long-term leverage — where data and architecture compound in value over time. President Corwyn Amendt drives execution, ensuring the platform evolves in lockstep with operational reality. Vice president Riyaad Ammantoola brings a delivery-first mindset shaped by pensions, analytics, and service design, while senior technical strategist Rao Thudi anchors the platform with the deep systems expertise required to keep complex environments stable and scalable. This isn’t innovation theater. It’s applied systems thinking. From foundation to flywheel Over the past several years, Oliver has invested heavily in the fundamentals: API infrastructure, group billing, multi-plan administration, data integrity, and disciplined onboarding frameworks. That foundation now powers something more important — momentum. New clients go live faster. New capabilities layer in without destabilizing operations. New ideas move from concept to production without multi-year programs. The roadmap builds forward from there: expanded real-time capabilities in Oliver Connect, deeper API infrastructure, stronger support for pensions and multi-employer environments, and selective AI features focused on reducing administrative drag, not replacing human judgment. Consulting services continue to evolve alongside the platform, aligned to execution, not theory. A different definition of leadership Some companies lead with history. Others lead with promises. Oliver leads with architecture, execution, and results. We believe the next generation of insurance and benefits platforms won’t be defined by how long they’ve existed, but by how effectively they help organizations adapt, connect, and move forward in a complex world. That’s the work we’re here to do. And we’re just getting started.