We’re excited to welcome Matthew Caffiero to Fivetran as our new Vice President of Business Development.
Matthew joins us with deep experience leading global sales development teams and building go-to-market strategies that deliver results. Most recently at Dynatrace, he led a team of more than 120 SDRs across four continents and drove outbound and inbound strategies aligned to enterprise growth. Over the years, he’s built a reputation for developing strong teams, driving performance, and helping organizations scale with discipline and impact.
He also brings a sense of urgency, focus, and leadership shaped in part by his five years of service in the U.S. Army, where he served as an intelligence analyst and squad leader.
We sat down with Matthew to hear what brought him to Fivetran, what he’s focused on building, and what kind of talent thrives on his teams.
Q1: What was the moment you knew Fivetran was the right next step for you?
I’ve spent my career helping companies scale, but what drew me to Fivetran was the clarity of purpose. In every conversation during the interview process, it was clear that the mission here is focused and meaningful. Moving data should be simple, reliable, and secure, and Fivetran is delivering on that promise. Combine that with the momentum, the product, and the people, and it felt like something I wanted to be part of. I saw a team that knows where it's going and what it stands for.
Q2: You’ve led global teams across some of the top names in enterprise tech. What’s the secret to building teams that not only perform, but keep growing?
It starts with hiring the right people. I look for individuals who are gritty, competitive, and willing to bet on themselves. You need people who are coachable but also hungry to grow. I’ve always believed that the SDR org is the engine room of the sales team, and when you build it right, it drives long-term success. At Fivetran, there’s a real opportunity to develop future AEs from within. My goal is to create a culture where people feel challenged, supported, and excited to take the next step in their careers.
Q3: Where do you see the biggest opportunity for Fivetran and its partners right now?
Every company is trying to figure out how to use AI, but most of them run into the same problem: their data isn’t ready. That’s where Fivetran plays a critical role. We help companies move and centralize their data in a way that is fast, governed, and reliable. That foundation is what makes AI possible. When we combine that with strong partnerships across the ecosystem, from Snowflake to Microsoft to Databricks, we unlock even more value. My focus is making sure those partnerships go deeper and drive real outcomes.
Q4: You’ve worked across just about every go-to-market motion. What makes a sales org truly click?
Alignment across the board. Sales, marketing, operations, and enablement all have to move in the same direction. When those pieces are connected, the results speak for themselves. At Fivetran, one of the biggest advantages is the clarity of the platform. We're not trying to be everything to everyone. That focus lets us go to market with confidence. My job is to make sure our sales development function is tightly integrated with the rest of the GTM motion so we're building quality pipeline that converts to real revenue.
Q5: You served five years in the Army before entering tech. Are there any lessons from that experience that still shape how you lead today?
Definitely. The Army taught me that preparation and discipline matter, but so does how you show up for your team. You succeed when people know the plan, trust the mission, and feel like they're part of something bigger than themselves. I try to lead from the front, be accountable, and stay close to the work. You can't ask your team to do something you're not willing to do yourself. That mindset, along with the resilience and urgency I learned in the military, has stuck with me throughout my career. Most importantly, of all the things I learned in my military service and since transitioning to tech, is that being an empathetic leader who truly cares about their people will always be my main priority.
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