Principal Product Manager - Monetization

Principal Product Manager - Monetization

Ontario, CAN or Hybrid from Waltham, MA

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!

We have an opening for a Principal Product Manager to architect the next generation of our revenue engine. This is a high-impact, strategic role at the intersection of our mobile‑first evolution and AI‑driven value delivery, where you will lead the charge in defining how Constant Contact unlocks enterprise‑grade value through innovative monetization frameworks.

In this role, you will be the "Squad Leader" for Monetization—acting as a single‑threaded owner of value. You won't just build payment pages; you will own the broader strategic monetization levers, including packaging, pricing models, and intelligent cross‑sell/up‑sell logic. You will bridge the gap between high-level strategy and relentless execution, driving ARPU expansion and modernizing our revenue engine for a mobile‑centric customer base.

This role exists because incremental change isn’t enough—we’re modernizing a legacy revenue engine for a mobile‑first, AI‑powered future.

• Own the Monetization Strategy
  :
  Go beyond transactional infrastructure to define how we package, price, and sell our value. You will develop strategies to drive ARPU expansion through smart cross‑sells, up‑sells, and net retention initiatives. This includes ownership of trials, paywalls, in‑product upgrade moments, plan comparisons, expansion paths, downgrades, and renewals.
• Lead with Velocity
  :
  Operate as the Squad Leader for the Monetization team, fostering a culture of autonomy and speed. You will move us from "output" (shipping features) to "outcomes" (driving revenue and retention). You are empowered to make high‑impact decisions, run fast experiments, and challenge legacy monetization assumptions in service of customer value and revenue growth.
• Drive the Mobile Transformation
  :
  Our customers want to work on mobile, but our legacy is desktop. You will lead the charge in reimagining monetization flows for a mobile‑first world, ensuring a seamless purchase and upgrade experience on any device.
• Leverage AI for Growth
  :
  Experiment with and implement AI‑driven monetization tactics, such as dynamic pricing models or predictive upsell prompts. You will also champion the use of AI tools to make the squad more efficient and data‑driven in its daily work.
• Collaborate Across the Business
  :
  Partner closely with Finance, Rev Ops, and Data & Analytics to model pricing impacts, validate hypotheses, and challenge assumptions using data and experimentation. You will serve as the connector between technical execution and business financial goals.
• Own Monetization Experimentation
  :
  Design, run, and scale continuous experiments across pricing, packaging, paywalls, and upgrade moments. Define hypotheses, success metrics, and decision criteria to de‑risk bets and compound learning. Drive measurable improvements across revenue retention, expansion, and monetization conversion—not just feature delivery.

• A Strategic Builder
  :
  You have 8+ years of Product Management experience in SaaS, with a specific track record in monetization, pricing strategy, or growth product management. You’ve operated as a single‑threaded owner for complex, cross‑functional initiatives with company‑level impact.
• Mobile‑Minded
  :
  You understand the constraints and opportunities of mobile commerce and have experience translating complex desktop workflows into intuitive mobile experiences.
• Data‑Obsessed
  :
  You live in the data. You are comfortable working with Data Analysts to dissect ARPU, LTV, CAC, and churn metrics to inform your roadmap. You are fluent in revenue…