Remote Senior Program Manager Jobs in Boston, MA

Our Team
Cimpress businesses and their in-house/third-party vendors (fulfillers) manufacture customized products that help our end-customers make an impression. In fulfilling the demand for such customized products, we are not only faced with the fulfillment problems like any other ecommerce company, but also have the challenge of manufacturing and delivering products unique to each customer's needs, on time and at the lowest possible cost.
We are seeking a Principal Technical Program Manager to take the helm in our Fulfillment Organization. In this role, you will be responsible for orchestrating highly complex, high spotlight initiatives that span Cimpress. You will not only drive strategy and execution framework across multiple massive fulfillment programs, but you will also lead, mentor, and grow a small, high-performing team of technical program/project managers.
What You Will Do

• Lead and Manage a small, but high-impact team: Directly manage and mentor a small team of program and project managers. You will operate as a "leader of leaders," establishing best practices, ensuring strategic alignment, and elevating the delivery capabilities of your entire team.
• Domain-Level Scope Ownership: Drive the execution strategy for multiple highly complex programs within Fulfillment. You will oversee the translation of executive fulfillment strategies into highly structured, technically sound execution roadmaps.
• Cross-Functional Stakeholder Alignment: Operate at the highest levels of the organization, bridging the gap between Global Fulfillment Executives, Plant Operations, and Core Engineering. You will manage complex, ambiguous stakeholder environments and build consensus on system-wide technical rollouts.
• Drive Clarity in our Domain: Ensure our organization is clear on our current and upcoming investments, latest status, blockers, and what success means.
• Accountability for System-Level Outcomes: You will design feedback loops and governance models to ensure that our technical initiatives drive tangible business outcomes. That means defining success and ensuring accountability
  to accomplish those goals.

Your Qualifications
At Cimpress, we are striving to hire individuals that add new ideas and perspectives to our teams and enhance our culture. No matter your background or work experience, we strongly encourage you to apply-even if you feel that you don't meet the exact requirements or have the same qualifications. You might be a great candidate for this or other opportunities.

• Experience: 8+ years of Program Management experience, with a proven track record of managing complex systems in fulfillment, supply chain, logistics, or large-scale e-commerce manufacturing environments.
• Comfortable in the "Gray": Proven ability to navigate highly ambiguous, domain-level initiatives. You are a master at balancing many inputs, factors, and feedback and guiding those around you to find clarity and make great decisions
• Communication & Influence: Elite written and verbal communication skills. You can distill product strategy, technical architectures, and fulfillment constraints into clear, high-impact business narratives for executive leadership.
• People Leadership: 2+ years of direct people management experience, with a passion for coaching and professional development of program/project managers.
• Balance a Bias for Action with being a guardian of our Product: We are building the next great Fulfillment product to serve a variety of businesses in Cimpress. Most projects we run are through the deployment of our Product. We want to execute quickly on projects, but not in a way that detracts from building a high integrity, quality software system

Why You'll Love Working Here
We encourage our engineers to think like owners - to continue to act small as we grow. Every team defines their own roadmaps, and uses the programming languages and technologies that suit them best. This helps us have a big impact at the enterprise level while still feeling small and nimble. We have a Remote-First operating model and culture, with team members in over 15 countries and 30 US states, offering autonomy and the flexibility to work from home. Cimpress also provides collaboration spaces for team members to work physically together.
About Us
Led by founder and CEO Robert Keane, Cimpress invests in and helps build customer-focused, entrepreneurial mass customization businesses. Cimpress Technology develops cutting-edge, best-in-world software that our mass customization businesses use to create personalized physical (and digital) products, for over 17 million global customers. Our businesses can choose the solutions that work for them, or assemble any custom combination they need. This makes it easier and faster to do things like introduce new products, reach customers and track orders. And this kind of innovation keeps customers coming back.
Commitment to Diversity, Equity, & Inclusion
Cimpress exists to help our customers live their dreams. Each dream is unique - and the Cimpress team needs to be as well. We believe in the unique contributions of everyone within a diverse global organization. We are collaborative, inclusive, and innovative. We strive to role model and live an inclusive culture of fairness, respect and belonging for all. And we work together to empower each other, creating a space in which each of us can spark our next great idea.
Equal Opportunity Employer
Cimpress Technology, a Cimpress company, is an Equal Employment Opportunity Employer. All qualified candidates will receive consideration for employment without regard to race, color, sex, national or ethnic origin, nationality, age, religion, citizenship, disability, medical condition, sexual orientation, gender identity, gender presentation, legal or preferred name, marital status, pregnancy, family structure, veteran status or any other basis protected by human rights laws or regulations. This list is not exhaustive and, in fact, in many cases, we strive to do more than the law requires.
Compensation:
US Target Hiring Range :$133,000.00 - $225,000.00 Per Year
Cimpress/Vista is committed to transparent and competitive compensation. In alignment with our compensation philosophy,
the target hiring range is based on total cash compensation across our multiple U.S. pay zones. The actual salary offered will depend on factors such as location, education, training, and experience. Cimpress/Vista offers a comprehensive benefits package, including health, wealth and wellness programs, as well as long-term equity incentives, subject to eligibility.
Due to current US government policy changes, we are currently not sponsoring new H-1B petitions subject to the $100,000 filing fee under the September 2025 Presidential Proclamation. Candidates with existing work authorization or H-1B status not subject to this fee may still be considered.
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