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 the trusted advisor for both our partners 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 that combines product management, delivery, client success, 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.

Responsibilities

• Own 3–5 client engagements from discovery through successful delivery.
• Build trusted relationships with founders, executives, and client stakeholders.
• Lead recurring client meetings, establish agendas, document decisions, and drive follow-up actions.
• Translate ambiguous business problems into structured product requirements and delivery plans.
• Break large initiatives into realistic milestones with clear priorities and timelines.
• Define product requirements and acceptance criteria that enable engineering teams to execute with confidence.
• Partner closely with engineering and design teams to align priorities and remove delivery risks.
• Balance client expectations with engineering capacity while protecting delivery commitments.
• Identify delivery risks early and proactively recommend solutions before they impact timelines.
• Handle client escalations professionally while maintaining strong long-term relationships.
• Maintain accurate delivery forecasts across multiple concurrent engagements.
• Present product strategy, delivery plans, and recommendations to executive stakeholders.
• Collaborate with leadership during proposal reviews, project planning, and delivery scoping.
• Leverage AI tools such as Claude or ChatGPT to improve planning, documentation, communication, and decision-making.
• Continuously identify opportunities to improve delivery processes, documentation, and operational efficiency.

Requirements

• 6+ years of experience in Product Management, Product Delivery, Technical Program Management, or a similar customer-facing leadership role.
• 3+ years working directly with external clients, enterprise stakeholders, or strategic customer accounts.
• Experience managing multiple software delivery engagements simultaneously.
• Strong product management background with the ability to translate business requirements into technical execution.
• Demonstrated experience scoping complex initiatives into realistic delivery plans.
• Excellent written communication skills with experience writing client-facing documentation, product requirements, and executive communications.
• Strong executive presence with the confidence to facilitate difficult conversations and manage stakeholder expectations.
• Technical fluency across APIs, integrations, cloud applications, software architecture concepts, and modern product development practices.
• Experience partnering closely with engineering teams throughout the software development lifecycle.
• Strong organizational skills with exceptional attention to detail.
• Ability to operate independently with minimal supervision in fast-paced startup environments.
• Demonstrated experience using AI tools such as Claude, ChatGPT, or similar to improve day-to-day productivity.

Preferred

• Experience working in software consulting, digital agencies, or professional services organizations.
• Experience managing outcome-based or fixed-scope software engagements.
• Background in insurtech, fintech, healthtech, fitness, or enterprise SaaS.
• Previous experience as a Head of Product, Senior Product Manager, Product Lead, Technical Program Manager, Engagement Manager, or Delivery Lead.
• Experience working in both startup and enterprise environments.
• Experience managing cross-functional teams.
• Experience working directly with founders and executive leadership teams.
• Demonstrated ability to manage multiple clients while maintaining exceptional customer satisfaction.

Benefits

• 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