Head of Technology Strategy & Operations

At Rival, we’re redefining what technology means in insurance. As a modern InsurTech company, we believe in building elegant, intelligent systems that empower clients, unlock data, and scale with purpose. But we know that great technology doesn’t build itself—it’s crafted by curious, collaborative, and mission-driven people. Joining Rival MeansMeaningful Impact: Your work directly influences how brokers, underwriters, and clients experience digital insurance—helping shape an industry ripe for innovation. Remote-First, People-First: We’re a remote-first team that values trust, transparency, and flexibility—because where and how you work should help you thrive. Culture of Curiosity:

We prioritize learning, feedback, and experimentation. Whether exploring AI tools or optimizing workflows, your ideas won’t just be welcomed—they’ll be expected. Technology with Purpose: From our Azure-based infrastructure to our evolving AI strategy, you’ll be working with a modern stack designed to solve real-world problems at scale. Leadership That Listens: You’ll work directly with executive leadership in an environment that values alignment, autonomy, and accountability. This role is a strategic and operational technology leader responsible for aligning engineering execution with the broader business roadmap.

This role combines strategic foresight and hands-on delivery mindset —ideal for a high-growth, innovation-driven environment. You will oversee software development, infrastructure, AI enablement, DevOps, IT operations, and cybersecurity. You’ll partner closely with Product, Data, and Executive teams to drive business impact, coach technical leaders, and scale modern systems, tools, and teams. Key Responsibilities Strategic Technology LeadershipDevelop and lead a multi-year technology strategy aligned with business goals and evolving customer needs. Champion the use of AI, automation, and experimentation to drive platform intelligence and operational efficiency. Translate business goals into scalable, secure, and user-centric technical solutions.

Engineering & Delivery OversightLead software engineering execution across multiple teams through planning, coaching, and prioritization. Track delivery metrics (velocity, incident trends, cycle time) to improve visibility and accountability. Maintain engineering excellence through strong CI/CD, observability, and security practices. AI Enablement & InnovationDrive AI adoption across the tech stack—including LLMs, workflow automation, and developer tooling. Ensure implementations are robust, ethical, and aligned with business impact. Identify and implement automation opportunities to streamline internal operations. Cloud Infrastructure & DevOpsOwn the Azure cloud environment, including IAM, cost optimization, access policies, and infrastructure as code.

Partner with DevOps to ensure uptime, disaster recovery, and SLA compliance. Standardize modern DevOps practices across the engineering organization. IT Operations & Vendor ManagementManage IT operations in collaboration with third-party providers, including ticketing, provisioning, and cybersecurity. Ensure compliance with privacy, audit, and security requirements. Evaluate and manage technology vendors for infrastructure, AI, and enterprise tools. People & Culture LeadershipCoach SDMs and tech leads to grow leadership capacity and team performance. Foster a culture of psychological safety, continuous learning, and innovation. Promote clarity, trust, and inclusion in a fully remote and cross-functional environment.

Cross-Functional & Executive AlignmentAct as a liaison between tech, product, business, and executive leadership. Partner with Finance to lead budgeting and resource planning for tech initiatives. Communicate complex technical topics to non-technical stakeholders with clarity. Qualifications10+ years in technology leadership roles, including direct management of SDMs or technical leads. Proven success in SaaS or InsurTech environments with distributed teams and mission-critical systems. Deep experience with Azure cloud infrastructure, AI strategy, and modern DevOps. Must have knowledge of LangChain and it's applicationsTrack record of aligning technology with business outcomes and driving cultural transformation.

Clear and empathetic communication style with strong stakeholder influence. We are committed to fostering an accessible and inclusive workplace. If you require accommodation during the recruitment process, let us know—we’ll work with you to meet your needs. We appreciate all applications; however, only those selected for interviews will be contacted.