[Remote] Principal Product Manager, Agent-First

Note: The job is a remote job and is open to candidates in USA. Constant Contact is a company dedicated to empowering small businesses and organizations to succeed online. They are seeking a Principal Product Manager to lead the development of their customer-facing AI experience, ensuring it is trustworthy and effective for small business owners. This role involves defining product flows, collaborating with cross-functional teams, and communicating effectively with stakeholders.

Responsibilities

• Own the customer-facing AI experience end-to-end. Define the core flows, ship them, instrument them, iterate. The quality of these flows is the product
• Make the AI feel trustworthy. Small business owners won't hand over real work to an AI that doesn't show its reasoning, respect their constraints, or earn trust gradually. You'll define how the product communicates intent, surfaces tradeoffs, and graduates customers from supervised to autonomous use
• Pick the right leading indicators. Activation, time-to-value, weekly engagement, owner intervention rate, attributed outcomes. Retention is the lagging story — these are the levers. You'll commit to numbers and defend them
• Partner across product surfaces. Our customer-facing experience sits on top of shared platform capabilities used by other parts of the business. Coordinate with the PMs and engineers who own those layers to ship fast without creating tax for either side
• Be opinionated about AI UX. Decide where LLMs make the product magical and where they make it brittle. Own the eval bar for agent behavior — accuracy, safety, brand tone, customer-appropriateness. Have a strong point of view on when not to use AI
• Use AI to build, not just to ship. Make AI-assisted research, prototyping, and iteration default working modes for the team. Move from idea to tested artifact in days, not sprints
• Get out of the building. Talk to small business owners weekly. Sit in support tickets. Bring their voice into every roadmap conversation, loudly
• Communicate up and across. Pitch the roadmap to executives, jam with engineering on architecture, defend tradeoffs to design, and translate customer pain into requirements that engineers can actually act on

Skills

• 8+ years in product, with at least one specific example of 0-to-1 product you took from concept to scale
• SaaS experience required; SMB experience strongly preferred
• Genuinely AI-fluent. You've shipped LLM-powered features in production
• You understand prompt engineering, RAG, evals, and agent architectures well enough to argue with engineers about tradeoffs, and not just hand them a PRD
• Direct experience building agentic systems (not just AI features bolted onto existing products)
• Sharp on AI UX. You have strong opinions on when AI should be visible vs. invisible, when it should ask permission vs. just act, and the difference between AI that delights and AI that unsettles
• Metrics-driven without being metric-blind. You build clear input → output → outcome pyramids and know which qualitative signals dashboards miss
• Customer-obsessed about SMB owners specifically. You don't think SMB customers are dumb because they don't read documentation
• Bias toward action. You'd rather ship a rough version this week and learn than ship a polished version next quarter and guess
• Direct communicator. You give feedback kindly and clearly. You disagree in the room, commit when the call is made, and don't relitigate later
• Background in SMB SaaS or marketing technology
• Familiarity with multi-channel customer engagement
• Experience with PLG motions and self-serve onboarding
• A point of view on how AI is reshaping SaaS distribution and product design

Benefits

• Some roles may be eligible for additional on target commission pay or bonus
• The compensation package includes health and welfare benefits including paid leave
• We celebrate one another’s differences. We are proud of our culture of diversity and inclusion, and we're always working hard to strengthen and improve this culture. We have programs in place that bring us together on important issues and provide educational opportunities for all employees.
• Join the experts. If you're passionate about supporting businesses and organizations, you won’t find a better spot to share your talent. We’re dedicated to improving the quality of our product from a customer standpoint and have a true desire to enable the success of businesses, non-profit organizations, and community groups.
• You’ll have opportunities to grow your career. We encourage and support our team members to learn different aspects of the business, take on stretch assignments, seek coaching opportunities and professional development opportunities.
• A generous paid time off policy and a competitive benefits package that supports the health and well-being of you and your family
• At Constant Contact, we’re all about work flexibility and are proud to serve our customers as a hybrid workforce. Our hybrid work model combines the convenience of remote work with access to our great office locations to collaborate in-person, participate in live trainings, and socialize with colleagues.

Company Overview

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