Senior Product Manager II, AI-Powered Customer Engagement

POS-17855

The Opportunity

AI-powered proactive customer engagement is the future of customer success—using predictive analytics, behavioral triggers, and conversational AI to anticipate needs, surface solutions, and create value before customers even realize they need help.

As Senior Product Manager II for Proactive Engagement, you'll build the AI-driven experiences that transform how 268,000+ customers and millions of end users interact with HubSpot across every touchpoint. You'll drive the strategic evolution from reactive support tools into intelligent, contextual engagement that leverages AI to guide users to success at exactly the right moment.

This role sits at the intersection of clear strategic priority—enabling AI-assisted self-service through Customer Agent adoption—and greenfield opportunity to redefine AI-powered customer engagement. You'll own a substantial mission with the autonomy to shape not just live chat's roadmap, but Service Hub's entire self-service strategy.

What You'll Do:

Define the future of proactive customer engagement
You'll identify the biggest opportunities to transform reactive support into intelligent, anticipatory experiences. Working closely with engineering and UX, you'll define problems worth solving and guide technical teams toward AI-powered solutions that engage users at precisely the right moments across websites, in-app, and beyond.

Build intelligent, multi-modal engagement experiences
Create cohesive AI-driven experiences that span chat, in-app tours, contextual help, and various media types. You'll design how predictive analytics, behavioral triggers, and real-time personalization work together to guide users toward success—whether they're discovering features, troubleshooting issues, or exploring advanced capabilities.

Shape AI-powered engagement strategy across multiple surfaces
Your solutions will leverage contextual AI and intelligent orchestration to work seamlessly across HubSpot's platform—from initial website interactions to deep in-product experiences. You'll define how proactive engagement evolves as users journey from prospects to power users, using predictive intent recognition and behavioral analysis.

Drive Customer Agent adoption through intelligent engagement pathways
Create natural, AI-powered pathways that introduce users to Customer Agent capabilities through contextual, value-driven experiences. You'll design smart handoffs between proactive engagement and AI-assisted self-service, ensuring the transition feels organic and valuable rather than forced.

Pioneer conversational AI and autonomous engagement
Build experiences where AI agents can proactively reach out with personalized solutions, execute tasks autonomously, and continuously learn from user interactions. You'll shape how HubSpot's engagement tools evolve from reactive chat to predictive, conversational experiences that anticipate and solve customer needs.

Influence AI-powered self-service strategy across Service Hub
Your work directly impacts how HubSpot's Self-service Product Group approaches the "Scale Support" mission today and the "Drive Retention" focus tomorrow. You'll have significant influence on product direction as the team evolves toward AI-powered, predictive customer success experiences.

What You’ll Bring:

Extensive product management experience with a track record of owning complex, high-usage products. You understand how to balance strategic vision with tactical execution, especially in AI-powered customer experiences.

Deep customer empathy and AI product intuition with the ability to translate user pain points into intelligent, predictive product opportunities. You've built AI-powered features that customers genuinely love and that learn from user behavior.

Experience with AI-powered engagement platforms and predictive systems preferred. You understand how conversational AI, behavioral triggers, predictive analytics, and multi-modal experiences work together to create cohesive, intelligent user journeys.

Systems thinking and the ability to see connections across touchpoints, user journeys, and AI capabilities. You can design experiences that feel seamless whether users start on the website, in-app, or through different AI-powered interaction modalities.

Comfort with AI product development and emerging technologies. This role has strategic clarity around AI-powered engagement but plenty of room to shape how predictive analytics, conversational AI, and autonomous agents cr