Senior Product Manager in Braintree

Based in Braintree, Lolly is a leading software and technology firm in the hospitality sector, producing a wide range of state-of-the-art technology solutions, including robot waiters, facial verification, mobile apps, EPOS and payment solutions. Our mission is to make technology simple by implementing the best solutions, incorporating the most reliable, intuitive technology, and following this with first-class after-sales customer care. We exist to create a technology hub for now and in the future.

About the Role

The Senior Product Manager at Lolly will be responsible for owning the strategy, development, and lifecycle of key product areas across the business. This role ensures that products are customer-focused, commercially viable, technically robust, and scalable as Lolly continues to grow. Working closely with Operations, Projects, Sales, Account Management, and Support, the Senior Product Manager will translate customer and business needs into clear product direction, ensuring seamless delivery from concept through to live deployment and ongoing improvement. You'll work across a full stack of hardware, software, and services: EPoS systems, mobile apps, payment integrations, and emerging AI capabilities. This role requires a strong technical understanding, particularly within EPOS and payments, and the ability to simplify complex systems into clear, actionable product decisions.

Responsibilities

• Own the end-to-end product lifecycle across assigned product areas, from discovery to delivery and iteration.
• Define and maintain clear product roadmaps aligned to business strategy and growth objectives.
• Balance innovation with stability, ensuring products remain reliable in live customer environments.
• Prioritise work based on customer value, commercial impact, compliance requirements, and technical feasibility.
• Connect big-picture thinking (AI-enabled experiences, platform scalability, market positioning) with concrete, measurable outcomes.

Customer & Business Alignment

• Act as a key voice of the customer, understanding operational realities across hospitality, education, and healthcare sectors.
• Synthesise insights from Account Management, Sales, Support, and direct customer engagement to validate needs and spot opportunities.
• Ensure product decisions support customer adoption, usability, and long-term success.
• Stay ahead of market trends, competitor activity, and emerging technology, particularly AI-enabled solutions that could reshape customer expectations.

Governance, Quality & Compliance

• Ensure product decisions consider payments regulation, security, compliance, and operational impact.
• Maintain accurate documentation to support internal teams and customers.
• Identify risks early and proactively manage dependencies across teams.
• Monitor product performance, customer feedback, and operational data to inform improvements.
• Contribute to the long-term evolution of Lolly’s product portfolio.

Key Skills & Requirements

• 5+ years’ experience in Product Management within a technology or software-led business.
• Strong technical understanding, ideally within EPOS, payments, or complex platform products.
• Proven ability to translate complex requirements into clear product direction.
• Experience working cross-functionally with engineering, commercial, and operational teams.
• Strong communication, prioritisation, and decision-making skills.
• Experience within hospitality technology, fintech, or regulated environments.
• Exposure to AI-driven or data-led products.
• Experience scaling products within a growing business.

Preferred Qualifications

• Degree in a relevant field or equivalent industry experience.
• Product management or agile certifications.
• Experience supporting multi-product or multi-sector platforms.