Senior Director, Product Strategy & Operations Boston, MA

Senior Director, Product Strategy & Operations

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’re looking for a Senior Director of Product Strategy & Operations to serve as the operating system for our Product and Design organization. In this highly visible role, you’ll partner closely with the Chief Growth Officer and Product leadership to ensure our strategy is clear, our execution is strong, and our organization is operating at peak effectiveness. This role is ideal for a product‑minded leader who thrives at the intersection of strategy, operations, and storytelling—and who loves turning complexity into clarity.

• Own and orchestrate the end‑to‑end product planning and strategy process, ensuring we have a clear, actionable, and data‑backed point of view on what we build and why. Partner directly with Product & Design leadership to shape strategic priorities across the full product portfolio, focusing on impact and value rather than individual product lines.
• Serve as the primary bridge between Product and cross‑functional partners—including Engineering, Marketing, Sales, Customer Success, Support, and Finance—to align dependencies, timelines, and execution.
• Ensure the broader organization is aligned and brought along as Product leads strategic initiatives.

• Architect and drive the product narrative for Board of Directors meetings, ELT reviews, and other executive‑level forums.
• Translate complex product strategy, progress, and performance into clear, compelling stories that demonstrate outcomes, momentum, and impact.
• Support the CPO in preparing high‑stakes presentations and communications that align stakeholders and drive decision‑making.

• Define, build, and continuously improve the operating systems that enable the Product and Design organization to do its best work—including processes, tools, cadences, and cultural norms.
• Take a systems‑thinking approach to optimizing how work flows, focusing on leverage, speed, and quality rather than process for process’ sake.
• Maintain a backlog of systemic issues—cultural, procedural, or operational—that slow execution, and own the roadmap to resolve them.
• Ensure major operational or organizational changes are fully executed and embedded, not just announced.

• Use product, operational, and financial data to ground decision‑making, drive discussions, and improve execution across the organization.
• Build fluency across key product and business metrics, ensuring leadership has visibility into performance and progress.
• Actively explore and apply modern AI tools (e.g., ChatGPT, Cursor, Claude Code, and emerging agent‑based workflows) to increase efficiency, insight, and organizational impact.

What You’ll Bring:

• 10+ years of experience in product leadership, product operations, strategy, or a closely related role within a technology‑driven organization.
• A strong product foundation, with firsthand experience building, shipping, or leading products and teams.
  
  Proven ability to operate at both high altitude and ground level—shaping executive strategy while diving into workflows and execution details.
• Exceptional communication and storytelling skills, with experience influencing senior leaders and executive stakeholders.
• A builder‑operator mindset: comfortable challenging peers, pushing the status quo, and designing systems for leverage rather than control.
• High tolerance for ambiguity, with a natural instinct to create structure, frameworks, and clarity where none exist.
• A proactive, self‑directed approach with a strong sense of ownership and accountability…