Principal Product Manager, Agent-First at Constant Contact in Canada

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 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. Who you are 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. You understand they're brilliant operators who happen to hate marketing software. 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. Nice to haves 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. #LI-Remote #LI-HK1 The specific salary offered to a candidate may be influenced by a variety of factors including the candidate’s experience, their education and work location. In addition, some roles may be eligible for additional on target commission pay or bonus. The compensation package includes health and welfare benefits including paid leave. Pay Transparency - All Full Time Employees $159,500—$191,400 USD Why You’ll Love Us: 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. Application Deadline: 30 days. We may fill this job opening prior to the deadline if a candidate is selected by us. 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