With over two decades of experience shaping the marketing strategies of tech giants like Google and Facebook, Brad Ramsey has a proven record of scaling brands and driving customer engagement. Now, as the new Chief Marketing Officer at Shippo, he’s taking the helm of both the marketing and sales organizations. In this conversation, we explore his approach to unifying these teams, his vision for evolving the Shippo brand to serve larger enterprises, and the valuable lessons he’s bringing from his past successes to empower merchants and partners in the ever-changing e-commerce landscape.
You’re now leading both marketing and sales to drive growth across SMB, MidMarket, and developer audiences. How will your go-to-market strategy differ for each of these segments, and what initial steps will you take to ensure alignment between the two organizations?
It’s a fantastic opportunity to create a truly unified commercial engine. My first priority is to break down any silos and establish a single source of truth for our customer journey. For our SMB and developer audiences, the strategy will be heavily focused on a frictionless, self-serve model driven by clear, simple messaging and powerful digital marketing. For the MidMarket and larger organizations, it becomes a more high-touch, consultative approach. That’s where sales and marketing alignment is paramount—we’ll be building account-based marketing programs and content that speaks directly to their complex challenges, ensuring the sales team has the precise tools they need to close deals. It all starts with shared goals and a deep, mutual understanding of the customer, regardless of their size.
Your background includes scaling global marketing teams at giants like Google and Facebook. Drawing on that experience, what is your framework for evolving Shippo’s brand strategy as it expands to serve larger organizations, and how will you measure its impact on customer engagement?
Working at that scale teaches you that a powerful brand is built on a foundation of trust and reliability. As we court larger organizations, our brand strategy must evolve from simply being a great tool to being a strategic partner. This means elevating our story to focus on operational rigor, security, and the immense value we bring to complex shipping operations. We’ll be investing in thought leadership and case studies that showcase how we solve enterprise-level challenges. In terms of measurement, it goes beyond simple acquisition metrics. I’ll be looking closely at customer lifetime value, product adoption rates for our new capabilities, and brand sentiment analysis to ensure our message is resonating and building the long-term engagement that these larger partners expect.
At Pirate Ship, you successfully drove expansion into the small and mid-sized business segments. Could you share a key lesson from that experience and explain how you plan to apply that learning to accelerate Shippo’s platform growth with merchants and technology partners?
The most critical lesson from my time at Pirate Ship was the profound importance of radical simplicity. For small and mid-sized businesses, shipping isn’t their core competency; it’s a necessary friction point. We succeeded by obsessively removing steps and making the entire process intuitive. I’m bringing that same mindset here. For merchants, this means ensuring our technology-based solutions feel effortless, almost invisible, so they can focus on their actual business. For our technology partners, it means making integration and collaboration just as simple. My goal is to apply that lesson across the board, ensuring that whether you’re a single merchant or a massive platform partner, interacting with Shippo is the simplest part of your day.
Shippo’s mission involves empowering businesses with simple, technology-based shipping solutions. Can you walk me through your vision for creating stronger connections with merchants and partners, and provide an example of a marketing initiative you believe would effectively communicate this value proposition?
My vision is to transform our relationship with merchants and partners from transactional to communal. We aren’t just a service provider; we are a growth partner. This means creating a feedback loop where their voices directly shape our product roadmap. A marketing initiative I’m passionate about is creating a “Shippo Champions” program. This would go beyond a simple affiliate setup; it would be a community for our most engaged merchants and partners, offering them early access to new features, exclusive content on e-commerce growth, and a platform to connect with one another. This initiative would powerfully communicate our value proposition by showing, not just telling, that we are invested in their success and are building this platform together with them.
What is your forecast for the e-commerce shipping landscape?
I foresee a continued drive toward democratization and intelligence. The days when only the largest retailers could afford sophisticated shipping logic and optimized rates are over. The future lies in leveraging smart, accessible technology to level the playing field, allowing businesses of any size to compete and grow more effectively. We’ll see more predictive analytics, greater automation, and platforms that not only simplify logistics but also provide actionable insights to help merchants make smarter business decisions. Ultimately, shipping will become less of a cost center and more of a strategic lever for customer satisfaction and brand growth.
