Head of Operations, InsurePro

Company Overview Rex is a privately held ecosystem of entrepreneurial ventures led by Peter Rex, spanning real estate private equity, technology, insurance, and AI. We build businesses and investment platforms that generate both exceptional financial returns and meaningful societal impact. At the core of our strategy is investor engagement: attracting aligned capital partners who share our long-term vision. We are building the most compelling investor-facing ecosystem in the private markets. The role offers exposure to a uniquely diverse platform, combining institutional-quality real estate and high-growth tech ventures, all aligned under a singular mission-driven vision.

About Us Our mission is to catalyze human flourishing through stewardship, serving people in all nations. We seek a transcendent impact, second to none, crossing geographies and making a permanent mark on history. We aim to uplift investors, foster flourishing families, create enduring trust, and contribute to a more beautiful world through our investments, products and services, and new ventures. Our investments are primarily in real estate, with additional allocations to tech, energy, and alternatives, employing a downside-protected, long-term approach to investing. We are grounded in timeless morals and seek to preserve and grow both investor capital and our own.

The Opportunity Rex is hiring a Head of Operations to turn InsurePro’s early success into a scaled, enduring insurtech platform. The company is profitable and scaling, with a strong foundational book and carrier partners in place. This operator will own performance across sales, technology, and operations, ensuring speed, discipline, and accountability in execution to drive profitability at scale. Expert in customer success and retention, ensuring a seamless client experience that drives renewals, referrals, and long-term loyalty. Cultivates and expands carrier relationships, deepening existing partnerships while forging new ones that unlock growth, provide more selection, and create a pricing advantage. The ideal candidate has 6–9 years of experience, including P&L responsibility and a proven record of operational excellence in insurance and tech. Must command deep knowledge of the insurance landscape, including distribution, underwriting, and compliance, paired with sharp commercial instincts and fluency in leveraging technology and AI to drive efficiency and growth. Brings world-class people management and go-to-market chops, exceptional sales leadership, and a disciplined approach to triaging risk, keeping order, and maintaining compliance. Proficient in full-stack marketing, from website and SEO/AEO to digital ads, events, and social media, integrating brand, growth, and performance marketing into a unified engine that drives demand and accelerates sales velocity. Thrives in building systems, scaling teams, and continuously improving operational and client-facing processes to maximize growth and retention. Owns the systems, rhythm, and metrics that turn early traction into durable scale. Must be missionary to the bone, client-obsessed, and passionate to catalyze human flourishing via insurtech. Fully remote.

About the Role Rex is hiring a Head of Operations to turn InsurePro’s early success into a scaled, enduring insurtech platform. The company is profitable and rapidly expanding, with a strong foundational book and carrier partners already in place. This leader will own performance across sales, technology, and operations, ensuring speed, discipline, and accountability in execution to drive profitability at scale. You will be the connective tissue between product, sales, marketing, and carrier relations—ensuring operational precision, customer retention, and sustainable growth. You’ll cultivate carrier relationships, deepen existing partnerships, and forge new ones that unlock growth, improve selection, and create a pricing advantage. You’ll architect systems and rhythms that transform early traction into enduring scale, balancing innovation and compliance while keeping the customer at the center of everything. This is a hands-on, high-impact role for an operator with deep insurance and tech experience, proven P&L ownership, and the ability to translate strategy into flawless execution.

Key Responsibilities Drive operational excellence across sales, marketing, and client operations to achieve profitability and scale. Design and own systems that integrate sales, underwriting, and customer success workflows for efficiency and accountability. Oversee customer success and retention, ensuring a seamless client experience that drives renewals, referrals, and long-term loyalty. Cultivate and expand carrier partnerships, securing better coverage options, pricing leverage, and strategic alignment. Develop and execute growth systems combining digital marketing, SEO/AEO, brand, and performance channels into a unified demand engine. Own KPIs and reporting across sales velocity, client retention, profitability, and operational throughput. Implement and optimize technology solutions, leveraging automation, data, and AI to streamline processes and improve decision-making. Recruit, train, and lead high-performing teams with a focus on discipline, accountability, and continuous improvement. Maintain rigorous compliance and risk management frameworks across all operational and client-facing processes. Serve as right hand to the CEO, aligning daily execution with strategic goals and long-term vision.

Ideal Candidate Profile 6–9 years of experience in insurance, insurtech, or related sectors, including P&L ownership. Deep knowledge of the insurance landscape—distribution, underwriting, compliance, and technology integration. Proven track record of scaling teams and systems in a fast-paced, tech-driven environment. Expert in customer success and retention, with the ability to translate data into action. Skilled in sales leadership and GTM strategy, balancing creativity and discipline to drive results. Strong grasp of digital marketing, SEO/AEO, and performance marketing; able to integrate brand and growth into a unified engine. Demonstrated ability to build and manage carrier relationships that enhance product offering and pricing advantage. Adept at process improvement, automation, and operational system design. Missionary mindset: driven by purpose, disciplined under pressure, and relentless in execution. Fully aligned with Rex’s mission to catalyze human flourishing through business.

Rex Ecosystem-Wide Mission Catalyze Human Flourishing through our products and services and to elevate and further humanity in all our business dealings.

Rex Values / Rex Culture Customer Fanatic. We fanatically focus on customers, seeking to ever-deliver more value, and inventing and innovating on their behalf. Product/Service Passion. Our business thrives or dies by products and services. Ludicrous Speed. Our default pace is extremely fast. Time is precious, life is short, and moving fast is more fun and effective. FAWOMO. We will find a way, or make one. Loves Going to War. Prefers wartime to peacetime, always hungry to move forward, do more, and push growth. Chutzpah. Nothing ventured, nothing gained. Fortune favors the bold. Duc in altum. Fun. We should only do work, over the long run, that is fun, and work with fun people. Jokes and humor welcomed, PC stuff and uptight behavior prohibited. Never-Lose-Money Approach. Protects the downside, using careful analysis before deploying significant resources, and ensuring cash is plentiful, never risking what others have and need for what they do not have and do not need. Other-Centered. Idealist, desperate more than anything to leave an impact with their life by helping other people, seeing money as a means to serve. Creative Cost Cutting Constantly. There is always a smarter way, always room to cut, always ways to do more with less. A cost advantage is a competitive edge. Fewer, More Capable. Bias to as lean of a team as possible, with the highest competency, reducing communication and coordination, creating more effectiveness. Underdogs. What we have done is nothing compared to what we are going to achieve now. We are fighting to be the best, clawing and biting up and forward, aiming to be the champs, be number one. Scrappy AF no matter how much we accomplish. We have never arrived in our minds. We are the underdogs always. Other Attributes Valued. Point-blank forthrightness in conversation with teammates, brutally facing problems. Velvet glove with iron fist in human dealings. Shrewd as a serpent innocent as a dove. Hardcore work hustle. Invictus mentality. Swagger with humility. Quiet professionalism. Thrifty and not materialistic. Loves who they work with, loves what they do, and loves who we serve.

Compensation & Benefits Base Salary: $100,000 to $150,000 annually Opportunity for performance based bonus and/or equity in deals and funds

Benefits:

Comprehensive health, dental, and vision insurance 401(k) with company matching Fully remote work environment