Principal Product Manager, Agent-First
constantcontact • Remote, US or Remote, Ontario, Canada
No Relocation
Posted: May 12, 2026
Job Description
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
Additional Content
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