Principal Product Manager, Agent-First

At Constant Contact, we are seriously awesome people who take ownership and make an impact by operating with the mindset, integrity and courage of a small business owner. There’s something so profoundly rewarding about knowing that your work is empowering people everywhere to pursue their dreams. Here, we all play an integral part in helping business owners, entrepreneurs, non-profits and individuals to succeed by giving them all the help and tools they need to grow online. We’re energized by new challenges and new possibilities-and we’re just getting started! Constant Contact has helped millions of small businesses grow for over 30 years. We're now investing heavily in the next chapter — an AI-native product experience that does more of the work for our customers, across more of the channels they care about. This role leads product for our flagship customer-facing AI experience, with cross-functional reach into the platform capabilities that power it. You'll be the senior product leader on a small, high-trust team building something new. Executive sponsorship is real, the ambition is high, and the surface area is large. You'll set the bar for how AI shows up in our product — what it does, what it doesn't, and how SMB owners learn to trust it. ### What you'll do

• Own the customer-facing AI experience end-to-end. Define the core flows, ship them, instrument them, iterate. The quality of these flows the product. - 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. - 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. - 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. - 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 to use AI. - Make AI-assisted research, prototyping, and iteration default working modes for the team. Move from idea to tested artifact in days, not sprints. - Talk to small business owners weekly. Sit in support tickets. Bring their voice into every roadmap conversation, loudly. - 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. ###