Senior Product Delivery Lead

As a Senior Product Delivery Lead , you will own the success of multiple client engagements from discovery through delivery, acting as a trusted advisor to both our clients and internal teams. You will lead product discussions, shape delivery plans, manage stakeholder relationships, and ensure every engagement moves forward with clarity and predictability. This is a highly cross-functional leadership role combining product management, software delivery, client leadership, and strategic execution . You will work directly with the Founder, Head of Product, engineering, and design teams while partnering with executives and product leaders across multiple client organizations. We are particularly interested in candidates who have worked inside regulated product companies , especially in insurtech, insurance, healthtech, or fintech , and understand firsthand how regulatory, compliance, risk, security, and operational requirements influence product decisions and software delivery. Experience with insurance claims, underwriting, or policy-related products and workflows is especially valuable. Responsibilities Own 3–5 concurrent client engagements from discovery through successful software delivery. Serve as a trusted advisor to founders, executives, product leaders, and other key client stakeholders. Translate ambiguous business problems into clear product requirements, acceptance criteria, priorities, and delivery plans. Break complex initiatives into realistic milestones while managing scope, dependencies, timelines, and engineering capacity. Partner closely with engineering and design teams throughout the software development lifecycle to remove blockers and maintain execution clarity. Lead client conversations around priorities, progress, risks, trade-offs, and changing requirements. Anticipate delivery risks and recommend solutions before they impact commitments or client relationships. Maintain accurate delivery forecasts and provide leadership with clear visibility across concurrent engagements. Navigate regulatory, compliance, security, and operational constraints when shaping product and delivery decisions. Support proposals, estimation, project scoping, and engagement planning alongside company leadership. Leverage AI tools such as Claude, ChatGPT, or similar platforms to improve discovery, planning, documentation, communication, and decision-making. Identify opportunities to improve delivery processes and operational efficiency as the organization scales. 6+ years of experience in Product Management, Product Delivery, Technical Program Management, or a similar software-focused leadership role . 3+ years working directly with external clients, enterprise stakeholders, or strategic customer accounts. Proven experience owning multiple software delivery engagements simultaneously. Direct experience working inside a regulated product company , ideally in insurtech, insurance, healthtech, fintech, or another highly regulated software environment. Strong product management skills, including discovery, requirements definition, prioritization, scoping, and delivery planning. Experience navigating regulatory, compliance, privacy, security, risk, or governance requirements during product development. Strong executive presence with the ability to challenge requests, communicate trade-offs, and manage expectations confidently. Technical fluency across APIs, integrations, cloud applications, software architecture concepts, and modern software development practices. Experience partnering directly with engineering teams throughout the SDLC. Excellent written communication skills across product documentation, client communication, and executive-level materials. Strong organizational skills and the ability to operate independently in ambiguous, fast-paced environments. Hands-on experience using AI tools such as Claude, ChatGPT, or similar platforms as part of day-to-day work. Preferred Experience with insurance or insurtech products , particularly claims, underwriting, policy administration, or risk-related workflows. Experience with regulated products in healthtech, fintech, payments, banking, lending, or related industries. Experience working in both in-house product organizations and software consulting, professional services, or digital agencies . Experience managing outcome-based or fixed-scope software engagements. Experience working in both startup and enterprise environments. Experience leading cross-functional product, engineering, design, and QA teams. Experience partnering directly with founders and senior leadership. Experience applying AI to product discovery, requirements, delivery planning, or software development workflows. Location: 100% Remote Compensation: $7,000 to $8,000 monthly USD PTO: 25 days paid time off + 5-day year-end company closure Annual remote retreat Expense and equipment allowance