VIP Software Executive Leadership
Meet the leaders driving innovation across the P&C insurance technology ecosystem.
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James Makris is a serial entrepreneur, technology executive, and recognized thought leader within the Property & Casualty insurance industry, known for identifying emerging market inefficiencies and transforming them into scalable technology and intelligence platforms.
Over the course of his career, James has co-founded and helped scale multiple InsurTech and technology-enabled businesses across the insurance ecosystem, several of which have achieved successful strategic and private equity-backed exits. His experience spans software, claims operations, workflow infrastructure, data intelligence, and embedded financial technologies, with a consistent focus on creating differentiated platforms that align with evolving market dynamics.
Unlike many operators who follow established market trends, James is recognized for identifying raw, underserved opportunities early and building infrastructure layers that create long-term strategic value. His leadership philosophy centers around anticipating industry transformation before it becomes mainstream — aligning products, data, and monetization models with where the market is ultimately heading rather than where it currently resides.
As Founder and CEO of VIP Software, James has led the company’s evolution from a traditional SaaS provider into an emerging intelligence and financial infrastructure platform serving the P&C insurance industry. Under his leadership, VIP Software patiently built critical ecosystem scale across carriers, independent adjusting firms, service providers, and workflow participants — creating a highly defensible data and transaction network that now powers the company’s transition toward intelligence-driven monetization.
Today, VIP Software is positioning itself at the intersection of workflow infrastructure, benchmark intelligence, and embedded fintech through platforms such as RateIQ and RateIQ Exchange — initiatives designed to transform operational claims data into actionable market intelligence and new economic opportunity across the insurance ecosystem.
James is widely regarded for his ability to pivot and strategically realign business models as markets evolve — including VIP Software’s transition from workflow-centric SaaS toward intelligence, data monetization, and embedded financial infrastructure. His long-term vision continues to focus on building the intelligence layer for the insurance industry while enabling carriers, firms, and independent professionals to operate with greater transparency, efficiency, and economic alignment.
Michael Battis has been part of VIP Software since day one, helping scale the company from an early-stage startup into a growing technology platform serving the P&C insurance industry. Over more than 13 years, he has advanced through multiple leadership roles spanning finance, enterprise sales, and revenue operations, giving him a unique end-to-end understanding of both the business and the industry.
As CRO, Michael leads strategic growth initiatives, enterprise partnerships, and revenue expansion efforts across carriers, IA firms, and service providers, while helping shape the long-term commercial vision of VIP Software.
Chris Kennedy brings nearly 15 years of leadership experience from N-able, where he helped build and scale global sales development and customer success operations across North America. Throughout his career, Chris has focused on creating scalable systems, aligning teams, and driving structured revenue growth through repeatable execution.
At VIP Software, Chris leads operational strategy and growth initiatives, helping transform emerging products and market momentum into scalable, long-term execution across the organization.
With more than 20 years leading enterprise technology and solution architecture initiatives, Alex has built and integrated complex systems across Fortune 1000 companies, SaaS platforms, and high-growth startups. Before joining VIP Software as CTO, he led enterprise consulting and infrastructure operations roles at Mavenlink and ZeroLag Hosting.
Alex drives innovation, scalable solutions, and aligns technology with business goals to deliver measurable value across the organization.
Sara Lasseter has played a critical role in scaling operations, customer success, and data intelligence initiatives across VIP Software for more than five years. With experience spanning client services, executive operations management, and strategic planning, Sara has become a key leader behind VIP's operational infrastructure and partner experience.
Today, Sara leads operational strategy and oversees VIP's growing mimia™ data ecosystem, helping carriers, IA firms, and service providers better understand industry trends through advanced analytics, Power BI reporting, and data-driven insights. Her cross-functional leadership has also supported marketing initiatives, customer success programs, and enterprise partner engagement across the organization.
Artie Makris has spent more than a decade leading strategic marketing, brand development, and growth initiatives across the technology and SaaS industries. Prior to joining VIP Software, he held leadership roles at N-able, where he focused on strategic marketing operations, revenue growth initiatives, and partnership development within large-scale channel ecosystems.
At VIP Software, Artie leads the company's market positioning, product branding, go-to-market strategy, and digital growth initiatives, helping shape the public vision and industry presence of platforms including RateIQ™, VIP Connect™, and VIP Wallet™.
Jason Brandes brings a strong combination of insurance industry expertise and enterprise technology sales leadership to VIP Software. Prior to joining the company, he held leadership and consulting roles at EagleView and Homee, where he specialized in carrier relationships, virtual adjusting technology, underwriting solutions, and scaling SaaS-driven insurance operations.
At VIP Software, Jason leads enterprise sales and strategic carrier engagement initiatives, helping expand adoption of the company's technology platforms across insurers, IA firms, and service providers throughout the claims ecosystem.
Gabriel Vella brings a unique combination of product strategy, systems integration, infrastructure engineering, and enterprise SaaS experience to VIP Software. Over the past decade, he has architected and delivered complex CRM, ERP, and workflow platforms while working across AWS, Azure, automation, and enterprise-scale SaaS environments.
At VIP Software, Gabriel leads product strategy and platform modernization efforts across the P&C insurance ecosystem, including the development of VIP Connect™ and critical integrations with Guidewire ClaimCenter, Xactimate, Snapsheet, and Cotality. He has played a key role in stabilizing enterprise carrier integrations, modernizing legacy infrastructure, and driving scalable product innovation across the organization.
Leads RateIQ™'s growth, digital acquisition, and market expansion initiatives across the Property & Casualty insurance sector. Holding a Master's degree in Marketing, she oversees social media, SEO, digital campaigns, and growth infrastructure, driving customer acquisition, pipeline generation, and brand awareness throughout the insurance ecosystem.
At VIP Software, Kasia leads digital growth, brand visibility, and market expansion initiatives across the P&C insurance ecosystem. She oversees SEO, social media, content strategy, and demand generation programs that strengthen RateIQ™'s market presence, drive qualified engagement, and support customer acquisition efforts. Her work plays a key role in expanding industry awareness, accelerating adoption, and building sustainable growth infrastructure across the organization.
Benny AI™
Chief Intelligence Hound (CIH) | RateIQ™
"Benny AI™ is the intelligence engine and conversational operating layer behind RateIQ™, designed to help carriers, IA firms, and independent adjusters make faster, smarter, and more profitable decisions across the claims lifecycle. Embedded directly into the platform experience, Benny powers the Ask Benny™ interface — transforming complex operational, pricing, and market data into actionable insights through natural conversation.
Benny continuously analyzes anonymized claims data, regional market trends, vendor performance, fee schedules, and operational workflows to surface benchmarking intelligence, strategic recommendations, and predictive insights in real time. Its role extends beyond automation, serving as the engagement and intelligence layer that drives adoption, retention, and workflow optimization across the RateIQ™ ecosystem.
Through integrations with RateIQ™ and VIP Connect™, Benny AI™ acts as the connective intelligence layer across the platform — helping insurance organizations modernize operations, improve decision-making, and unlock greater visibility into performance and profitability."
