Principal Product Manager (AI)

TL;DR

Principal Product Manager (AI): Lead the flagship customer-facing AI experience for SMB owners with an accent on agentic systems, trustworthy UX, and cross-functional platform integration. Focus on defining core flows, selecting leading metrics, and iterating based on customer feedback and evaluations.

Location: Remote, US or Remote, Ontario, Canada

Salary: $159,500 - $191,400 USD

Company

SaaS platform that has helped millions of small businesses grow online for over 30 years, now investing in AI-native product experiences across customer channels.

What you will do

• Own end-to-end customer-facing AI experience: define core flows, ship, instrument, and iterate.
• Build trust in AI by communicating intent, surfacing tradeoffs, and guiding customers from supervised to autonomous use.
• Select and commit to leading metrics like activation, time-to-value, engagement, and owner intervention rate.
• Partner with PMs and engineers on shared platform capabilities to enable fast shipping.
• Define AI UX standards, evaluation criteria for agent behavior, and when not to use AI.
• Use AI tools for research, prototyping, and iteration to accelerate development.
• Engage directly with SMB owners weekly and incorporate their feedback into roadmaps.
• Communicate roadmaps to executives and translate customer needs into actionable requirements.

Requirements

• 8+ years in product, with 0-to-1 launch experience; SaaS required, SMB preferred.
• Genuinely AI-fluent: shipped LLM features, understands prompt engineering, RAG, evals, agent architectures.
• Direct experience building agentic systems.
• Strong opinions on AI UX: visibility, permissions, delight vs. unsettling.
• Metrics-driven with input-output-outcome frameworks and qualitative insights.
• Customer-obsessed with SMB owners.
• Bias toward action and direct communication.

Nice to have

• Background in SMB SaaS or marketing technology.
• Familiarity with multi-channel customer engagement.
• Experience with PLG and self-serve onboarding.
• Views on AI reshaping SaaS distribution and design.

Culture & Benefits

• Hybrid work model with remote flexibility and office collaboration options.
• Competitive compensation including health/welfare benefits, paid leave, and potential commission/bonus.
• Culture of diversity, inclusion, and continuous learning with growth opportunities.
• Support for career development through stretch assignments, coaching, and professional programs.