Lead Software Engineer

We are looking for a Lead Software Engineer to join the Retention Zone and lead the charge on bringing AI into subscription products to drive subscriber value through new and engaging experiences. This is a hands-on individual contributor role for someone who can identify where AI creates real subscriber value, architect the right solutions, collaborate with Product teams to prioritize initiatives, and build impactful features - while also elevating how the broader engineering organization approaches and works with AI.

In this role, we are looking for someone who will not just advise, but actively prototype, ship, and iterate on AI-powered features that create a meaningful impact for subscribers. The engineer will work closely with Content Engagement and Search & Discovery product teams to bring these experiences to life., * Identify the highest-leverage opportunities to embed AI into our products - from intelligent content recommendations and personalization to smarter search and completely new experiences that add value to our subscribers.

• Partner closely with the Product Managers for Content Engagement and Search & Discovery to shape roadmaps, define AI-driven features, and ensure technical approaches align with subscriber and business goals
• Design and build AI-powered features end-to-end: data pipelines, model integration, APIs, and the product surfaces that subscribers interact with
• Prototype quickly, validate with real usage, and iterate toward production-quality solutions
• Establish the team’s AI engineering practices - evaluation frameworks, prompt management, fine-tuning approaches, observability, and responsible AI guardrails
• Partner with subscriber success to ensure AI features solve genuine subscriber problems and drive measurable outcomes
• Act as a technical force multiplier for the broader engineering org - reviewing AI-related work, mentoring engineers, and sharing knowledge across teams
• Stay close to the rapidly evolving AI landscape and bring the right tools and techniques in at the right time

• 7+ years of software engineering experience, with at least 2 years focused on shipping AI/ML features in production
• Deep familiarity with LLMs and modern AI tooling - prompt engineering, RAG, function calling, fine-tuning, vector databases, and agentic frameworks
• Strong software engineering fundamentals: system design, APIs, scalable data pipelines, and clean, maintainable code
• Experience owning AI features from concept through production and measuring their real-world impact
• A collaborative working style - comfortable partnering with product managers to translate customer needs into technical solutions
• Ability to communicate technical tradeoffs clearly to non-engineering stakeholders

GOOD TO HAVE:

• Prior experience in a lead IC role at a SaaS company
• Experience applying AI to content engagement, search relevance, or personalization problems
• Familiarity with AI safety, evaluation, and responsible AI best practices
• Background in a media domain

• 401K Plan with Company Match
• Professional Development
• Flex Spending
• Generous Time Off
• Community Volunteering
• Recognition & Awards
• Wireless Discount Plan
• Referral Program

Job Category: Web Development

Job Location: Boston

Skills: RAG, AI, LLM