[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.ResponsibilitiesOwn the customer-facing AI experience end-to-end. Define the core flows, ship them, instrument them, iterate. The quality of these flows is the productMake 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 usePick 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 themPartner 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 sideBe 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 AIUse 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 sprintsGet out of the building. Talk to small business owners weekly. Sit in support tickets. Bring their voice into every roadmap conversation, loudlyCommunicate 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 onSkills8+ years in product, with at least one specific example of 0-to-1 product you took from concept to scaleSaaS experience required; SMB experience strongly preferredGenuinely AI-fluent. You've shipped LLM-powered features in productionYou understand prompt engineering, RAG, evals, and agent architectures well enough to argue with engineers about tradeoffs, and not just hand them a PRDDirect 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 unsettlesMetrics-driven without being metric-blind. You build clear input → output → outcome pyramids and know which qualitative signals dashboards missCustomer-obsessed about SMB owners specifically. You don't think SMB customers are dumb because they don't read documentationBias toward action. You'd rather ship a rough version this week and learn than ship a polished version next quarter and guessDirect communicator. You give feedback kindly and clearly. You disagree in the room, commit when the call is made, and don't relitigate laterBackground in SMB SaaS or marketing technologyFamiliarity with multi-channel customer engagementExperience with PLG motions and self-serve onboardingA point of view on how AI is reshaping SaaS distribution and product designBenefitsSome roles may be eligible for additional on target commission pay or bonusThe compensation package includes health and welfare benefits including paid leaveWe 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 familyAt 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 OverviewConstant Contact makes digital marketing easy and effective for small businesses and nonprofits across the globe. It was founded in 1995, and is headquartered in Waltham, Massachusetts, USA, with a workforce of 1001-5000 employees. Its website is http://www.constantcontact.com.Company H1B SponsorshipConstant Contact has a track record of offering H1B sponsorships, with 20 in 2025, 16 in 2024, 16 in 2023, 33 in 2022, 21 in 2021, 27 in 2020. Please note that this does not guarantee sponsorship for this specific role.