Jonathan Hollander

About Jonathan Hollander

Across my career, I’ve learned a powerful truth: in insurance, growth without retention is fragile. The most durable path to sustainable success is to build “stickier” policyholders. This isn’t just a tactic; it’s a philosophy that aligns the interests of the client, agency, and carrier. Research from Bain & Company confirms this, finding that multi-policy customers are 3 to 5 times less likely to switch. This principle is at the core of every strategy I build and every program I launch.A strategy is only as strong as its execution. At People’s Trust Insurance, I architected and launched the WYO FEMA flood program and built a modern online flood rater from the ground up, cutting agency quoting time by 70%. These aren’t just technology projects; they are strategic enablers designed to make it simple for our partners to create those vital, sticky client relationships. This approach is built on a long track record of delivering at the intersection of innovation and leadership. As a founding executive at PhoneFusion, I delivered industry firsts, from the first visual voicemail platform on Android to Citibank’s global SMS verification system. At Sincuerda Wireless, I co-founded and scaled the company, managing a 938-person team and a $180MM budget to pioneer the systems that delivered internet to all Miami Beach hotels in 2002.The insurance industry stands at a crossroads. I see a future where AI becomes the agent\'s most powerful ally—anticipating client needs, simplifying risk, and freeing human talent to focus on what matters most: trust. My personal mission is to be one of the architects of this future. I believe the best technology amplifies people, not replaces them, and I build loyal, high-performance teams by leading by example and championing the alignment of business objectives with technological capabilities. I am always open to connecting with fellow leaders and innovators who are passionate about building the future of the insurance industry.

Experience

1. Executive Director of Agency Sales & Senior Executive Team Member

   People's Trust Insurance Company

   May 2018 — Present · Deerfield Beach, FL, US

   As a member of the senior executive team, I lead the vision, strategy, and execution of agency sales and account management for one of Florida’s largest property insurers, supporting a network of over 1,500 agencies. My mandate is to create sustainable growth and enduring partnerships by aligning agency, client, and carrier interests-**Executive Strategy & Growth:** Designed and executed the company’s primary growth strategy centered on building multi-policy households to drive client \"stickiness.\" This data-driven approach is proven to create 3–5x stronger client retention and greater agency stability-**Innovation & Enablement:** Serve as the bridge between corporate strategy and field execution, personally architecting practical solutions—including quoting engines and automation workflows—that simplify adoption and empower agency partners-**Sales Operations & Technology:** Architected and launched the companywide Salesforce CRM program, embedding visibility and efficiency into the sales process. I direct the data analytics and reporting functions to create a data-first sales culture with stronger forecasting and insights-**Key Accomplishments:**-**Launched & Grew the WYO FEMA Flood Program:** Created a new, significant agency revenue stream and expanded the company\'s market penetration-**Architected a Modern Online Flood Rater:** Delivered up to 15 quotes on one screen, cut agency quoting time by 70%, and measurably boosted sales conversions-**Piloted AI-Assisted Workflows:** Automated quoting and personalized client outreach, enabling agencies to efficiently scale multi-policy households.

Skills

• Project Management
• Agile Application Development
• Mobile Devices
• Executive Leadership
• Strategic Planning
• New Business Development
• Software Development Life Cycle (Sdlc)
• Actionscript 3
• Operations Management
• Technology Infrastructure Solutions
• Start-Ups
• Software Project Management
• Actionscript
• Business Process Improvement
• Go-to-Market Strategy
• Product Launch
• Online Marketing
• Product Marketing
• Team Leadership
• Bitcoin
• Telecommunications
• Product Development
• Negotiation
• Enterprise Software
• Sales Management
• Cryptocurrencies
• Business Strategy
• Adobe Air
• Saas
• Leadership
• Social Media Marketing
• Business Development
• Digital Marketing
• Lead Generation
• Vendor Management
• Mobile Applications
• Strategy
• E-Commerce
• Venture Capital
• Account Management