Zipline is a well-funded and quickly growing SaaS company that works with many of the world’s top retailers across many industries. We have best-in-class NPS and CSAT scores, and our customers rave about us. Plus, we are a fully remote company with employees all over Canada, the United States and beyond!

Hello, Creative Masterminds! Are you passionate about helping frontline companies revolutionize the way they operate? Are you looking for a career that allows you to work with the world’s best-known brands and Fortune 1,000 leaders?

Our mission is to provide frontline teams with effective tools that connect every level of their business and their employees love to use. You will help improve the way that this 4.4 trillion dollar industry communicates with its store employees and save them from sad, slow, inefficient systems (think fax machines, voicemails, and the postal service). People deserve better! We need your help to make this happen.

We are an early stage, well-funded company. We have awesome investors, great customers, and are looking for a Senior Product Manager, Actionable Insights to help us ensure our customers are successful with our product.

As a Senior Product Manager, Actionable Insights, you’ll play a pivotal role in shaping the way Zipline surfaces intelligence, insights, and guidance for our customers. You will be responsible for ensuring our platform transforms raw data into meaningful, actionable recommendations that drive better business decisions every day. With ownership of search, analytics, reporting, and Zippy (our conversational AI chatbot), you’ll help define how AI and data can be harnessed to empower retail teams at scale.

Working alongside experienced product leaders, you’ll prioritize features that make insights intuitive, proactive, and actionable—ensuring that decision-making becomes faster, smarter, and more impactful. You’ll collaborate closely with cross-functional partners to craft a strategy that not only enhances reporting and analytics, but also creates magical, AI-powered moments that simplify complexity and amplify value for our customers.

In this role, you’ll drive the growth of a comprehensive insights platform by:

• Defining and executing the product roadmap for insights, search, analytics, reporting, and conversational AI (Zippy).
• Leveraging Zipline’s unique data set to deliver both customer-specific and industry-wide insights that shape smarter decisions.
• Integrating AI-driven experiences that proactively surface insights, helping users act in the moment rather than react after the fact.
• Evolving reporting tools into decision-support systems that go beyond dashboards to provide guidance and recommendations.
• Building intuitive search and discovery experiences that help employees find the right information quickly.
• Continuously measuring adoption and impact of insights-related features to inform ongoing strategy and improvements.

You’ll be successful in this role by:

• Leading product discovery to deeply understand how retailers and frontline employees use data today—and what they need tomorrow.
• Partnering with engineering, data science, and design to build scalable, user-friendly AI-powered solutions.
• Conducting competitive analysis and customer research to identify opportunities to differentiate Zipline’s insights capabilities.
• Acting as a bridge between cross-functional teams to ensure alignment on vision, strategy, and execution.
• Championing a culture of evidence-based decision making, both within Zipline and across our customers’ organizations.

A Product Manager’s Role at Zipline includes:

• Connecting and communicating regularly with customers and coworkers to research real-world retail problems, build strong relationships, and amplify voices as we work toward building the most effective field enablement platform in the world.
• Learning and analyzing data to make informed decisions, monitor success of new features, and deepen market knowledge.
• Deciding and documenting through a written-first approach—writing pitches, outlining roadmaps, and capturing key decisions to ensure clarity and alignment.
• Shaping and building ideas through collaborative methods like breadboarding or sketching to ensure direction and functionality are clearly communicated.
• Product operations—developing scalable processes to manage product innovation and sustain growth across the company.

Must-haves:

• 8+ years of SaaS or enterprise product management experience, with 2–3 years in the retail domain preferred.
• Proven ability to translate business needs into actionable, AI-powered product experiences.
• Strong background in data analytics, search, and reporting with experience using BI tools, writing queries, and building decision-support systems.
• Experience bringing AI and machine learning products from concept to launch.
• Demonstrated success in defining and executing product strategy at a growth-stage company.
• Strong collaboration and communication skills to align with Marketing, Sales, Engineering, Customer Success, and customer stakeholders.
• Proven track record of shipping products that improve decision-making and create measurable business impact.

Nice-to-haves:

• We are for the frontline, by frontline. Having a background either working in retail or building software for frontline teams has been an important key to our product’s success. It’s not required but if you do have experience it will bring a ton of value to our customers and business.
• Working knowledge of the complexities of managing the operations of a retail store.
• Familiarity with conversational AI design and natural language interfaces.
• Familiarity with mobile app development process and app store ecosystems is a plus

More about you:

• Excellent verbal and written communication skills; you can translate complex concepts into simple, persuasive language.
• Curious, data-driven, and excited to push the boundaries of what’s possible with AI and actionable insights.
• Team player who thrives in fast-paced environments and enjoys collaborating across functions and with customers.
• Self-motivated, dependable, and committed to building products that make work smarter and more meaningful.
• Experience with the concepts described in Shape Up is an asset, but not required.
• Proficient in productivity applications such as JIRA, Google Apps, Slack, etc
• Ability to effectively communicate to, present to, influence or befriend all levels within an organization. Great at asynchronous communication.
• Team player with excellent collaboration skills to build relationships across the company with both ours as well as our customers.

Compensation:

At Zipline, we're committed to paying our team fairly, transparently, and in a way that supports growth. This role has a minimum annual salary within Canada of $148,800 CAD and a maximum of $223,200 CAD. This role has a minimum annual salary in the USA of $144,000 and a maximum of $216,000 USD.

The broad salary ranges reflect the growth someone will experience in the role—from developing skills to reaching expertise within their career level. We’ve found that hiring team members with the expectation of being accomplished in the role sets them up for success, which for this position on the USA band means a starting salary of $162,000 USD. Within the Canadian band, $167,400 CAD. Salaries below this point typically reflect someone with potential but still building the necessary skills, while salaries above are for individuals already excelling in the role, with a deep understanding of Zipline’s impact on customers, product, and company.

At Zipline, you’ll continue to have career development conversations with your manager to ensure your compensation grows as you advance.

Our salary ranges are determined by market, factoring in our revenue and employee size, paying competitively at the 75th percentile. In higher cost of living markets, we apply 5-10% multipliers on our ranges, depending on the location, to maintain competitive compensation and reflective of the increased expenses our team members face in those areas. While we primarily hire in Canada and the USA, we are a global employer, and all hiring regions will use the same methodology to determine fair and transparent pay.

Transparency is key to building trust in our compensation process. To better understand how this range is determined, we encourage you to ask as many questions as you'd like about compensation during the interview process to ensure clarity and confidence.

What’s in it for you:

Remote-first culture: Join a high performing, fully remote team and work where you're comfortable

Stock Options: Get meaningful ownership in a fast-growing, venture-backed company shaping the future of retail.

Time Off: Our flexible time-off policy ensures you stay refreshed and recharged. Plus, you’ll get a monthly stipend to get you out of the house—grab a coffee and work from your favorite spot!

Benefits: World-class medical, dental, and vision policies.

Team Connection: Annual company off-sites in fun locations. We've done New York, Costa Rica, Whistler, Palm Springs, San Diego, and Mexico City.

Sabbatical: A one month paid sabbatical after completing five years of working at Zipline.

Volunteering: Every quarter, Zipliners get a paid day off to volunteer for a nonprofit of their choice.

Learning: We support continuous learning and provide unlimited access to our Udemy Business account.

Great humans, great work: Work with kind, collaborative teammates who care about doing meaningful work and making a real impact. We value diversity of all kinds and are committed to building a diverse and inclusive workplace where we learn from each other. We are an equal opportunity employer and welcome people of all different backgrounds, experiences, abilities, and perspectives.

Want to learn more about how we work?

We may be remote, but we’re anything but disconnected. Zipline is a thriving, dynamic team spread across the globe—collaborating, innovating, and having a blast along the way.

Zipliners work from all over—vans, boats, Airbnbs, and everything in between. No office? No problem. Our culture still feels like one big hug.

Even though we’re distributed, we make space to connect—whether it’s our weekly all-company social or gathering in person at our yearly retreats. We’re building something meaningful together, and we’re glad you’re considering being a part of it.

We can’t wait to meet you!