Uplevel Blog

Expert Series: Q&A with Matt Swann, former tech leader at Amazon, Nubank, and Booking

Throughout his career in software engineering, Matt Swann went from a focus on skills and accomplishments to thinking in terms of how the work was done, which has helped him focus more on coaching and influencing teams. Here’s what he’s learned along the way.
Author: uplevel
Tags: Blog

Uplevel guides engineering teams to fulfill their highest potential. In this pursuit, we consult with all kinds of experts, and they always teach us something new. We introduced the Expert Series to share this wealth of knowledge.

Matt Swann’s entry into software engineering was an evolution. Early on in his career, he would label himself based on his technical skills and what he’d accomplished. Over time, he began to focus not only on what he did but how he did it. 

Matt transitioned from seeing his contribution in terms of technical skills to seeing it in terms of being able to coach people toward something new. As he started to focus more on influencing people and teams, his efforts were recognized, and it began to feel like he might be good at it.

Being curious to understand and get involved in the business also helped a lot. Matt started by taking more of a lead role on projects, and as he repeatedly delivered and earned respect, he was rewarded with a team.  

Matt has since held leadership roles at organizations such as Nubank, Booking.com, StubHub, Amazon, and more. Today, Matt serves in an advisory capacity to companies such as Uplevel as he focuses on thought leadership and continuing to help engineering organizations succeed.

What has been one of your greatest successes or something you’re most proud of as an engineering leader? 

I’m most proud of the talented people I’ve been able to attract and develop over time. When you have the right team and culture, you can do almost anything. It’s been a privilege to have helped shape the leading edge of e-commerce and financial services for companies like Amazon, Booking, and Nubank. 

Independent of all the products and platforms delivered, I’m humbled that so many of my team members have gone on to achieve success in such big roles in the industry. I’m even more humbled that they often still call for advice. 

It’s an amazing feeling to know you helped play a role in launching those careers, building high-performing teams, and making people feel like they’ve done the best work of their lives during our time together.

What has been one of your greatest challenges as a leader?

Alignment. As a technology leader building complex products and platforms, one is always making sure the mission and accountability are clear. Setting SMART goals with metrics and inspection mechanisms helps, but as a leader, a lot of alignment requires frequent stakeholder management. Making sure you are empathetic to customers’ needs and that they are well understood is critical. As a technology leader, developing a shared language and value system that is embraced across the business, product, and technology is key. 

How do you define engineering effectiveness? How do you measure it for your teams?

I think about three main buckets of engineering effectiveness when it comes to how software is built, deployed, and operated: 

  • Build: From a build perspective, I always like to start with the Say/Do ratio of teams. At the end of each period, did teams accomplish what they said they would? There are a variety of variables that you can inspect to help improve this ratio, including the amount of time engineers spend in meetings, backlogs, scope and story quality, and dependencies. It’s incredibly important to understand where work is stuck in the system. 
  • Deploy: From a deployment perspective, I tend to focus on DORA metrics like deployment frequency, lead time for changes, time to restore a service, and/or change failure rate. The right tooling and automation can help a lot here.
  • Operate: Operational burden can be one of the single biggest impacts on development teams. I leverage metrics like system availability, latency, ticket, bug, and error rates along with resolution time to understand the impact of on-call and operations on development teams.

In each of these cases, it’s critical to have tooling and systems that enable continuous inspection of the right metrics and trends. The more clarity you have, the more you can improve.

How do you balance product delivery and team health?

Very carefully. In the race towards business and product goals, it’s important to build a culture, operating model, and metrics that allow you to sprint when needed without impacting the long-term health and productivity of teams. 

It also means looking carefully at short-cut tradeoffs that enable short-term time to market but increase long-term technical debt. Sometimes you have to slow down in the short term —  delivering fewer features — to go fast in the long term by paying off technical debt or making longer-term platform investments. Even if you occasionally need to make a short-term trade off, committing to fast follow-on work to correct is key. 

Knowing and monitoring your teams and their health is also critical. It means not only having the right metrics and inspection mechanisms but building the right relationships and feedback loops to know when you’re stressing the boundaries.

As a leader, how do you communicate risk or status upwards and to your teams?

Quickly and transparently. When managing up, it’s important to ensure you’re painting the whole picture but getting to the point about risks, trade-offs, and most importantly, solutions. If you don’t have the whole picture, you need to be crisp about what you’re doing to get there and by when. 

As a technology leader, it’s critical that you communicate using terms business and product teams will understand, and create a shared language around your goals. Fundamentally, not much changes when communicating to teams versus managing up, other than getting to a more specific amount of detail regarding expectations and accountability. Folks need to understand the situation and the role they play to get the best outcome.

Reflecting on your past experiences, what data have you found most valuable to help you manage an engineering organization? Are there any hard metrics you’ve found useful?

Top-level, I tend to leverage Objectives and Key Results (OKRs) for annual goals and Big Hairy Ambitious Goals (BHAGs) for multi-year efforts. Key OKRs and BHAGs often include improvements to:

  1. Reduce technology costs.
  2. Improve system performance, scalability and availability.
  3. Improve productivity and time-to-market. 
  4. Reduce operational burden. 
  5. Deliver key platform improvements.
  6. Improve employee engagement. 
  7. Reduce security and risk events.
  8. Achieving product delivery goals.

Why is culture important for engineering teams? How do you build a good culture?

Culture is everything. A good engineering culture can foster innovation among the team. Because there is more communication and a clear common ground when the engineering culture is strong, employees tend to feel more comfortable being creative, thinking outside the box, and bringing new ideas forward. 

To me, culture starts with frequent communication, clear leadership principles and values, a well-understood mission, and a lot of openness (constantly asking for input) and empathy. I like to embed principles and values in every conversation and document where it makes sense. I also try to ensure people understand the mission and their roles through frequent communication and reinforcement. 

I also focus heavily on culture in the hiring process and look for strong culture fits.

How should engineering leaders view team performance?

Engineering team performance is the biggest leverage of any technology company. To create sustainable teams, it’s important to have a 360-degree view of performance and not just focus on business outcomes. 

It’s important for leaders to build a culture of accountability focused on key metrics that you routinely inspect to understand performance and what you need to do to improve it. This includes prioritization planning, delivery cycles, burnout, and operational burden.

What impact does bad decision making have on engineering teams?

Bad decision-making can be demoralizing for teams and, over time, affect productivity and attrition beyond directly impacting the business. I like to cultivate a fail-fast and blameless culture which means learning from mistakes and interpreting and applying failures as teachable and coachable moments vs. penalizing them as a bad decision. 

At times, I like to celebrate those failures. However, my aim as a leader is to help build the right metrics and support systems that enable teams to make more informed decisions, resulting in fewer bad ones.

What “bad decisions” do leaders make because they lack data or the right information?

When you don’t have the right information, it’s easy to make a bad and uninformed decision. This comes to a head most often in planning and prioritization when teams don’t have a good handle on the scope of work and/or the capacity of their teams relative to their effectiveness and productivity. Teams can often take on too much work, and their ability to deliver can be impacted by factors that could have been known and avoided with better data.  

How can leaders make smarter decisions (in general and with data)?

Smarter decisions almost always come as a result of better data and input from teams. It’s important not to be caught up in analysis paralysis, but you must understand the inputs, risks, and tradeoffs well, along with the varying inputs of teams, to get to the best outcome. Try to minimize subjective qualitative inputs where it makes sense and focus on the more tangible quantitative measures.

How can leaders empower their teams to make better decisions?

Create a culture and operating model that is open, empathetic, and data-driven. Ensure that teams have clear accountability for well-understood measures that are routinely inspected and aligned with stakeholders. Enable teams to fail faster and learn more with strong feedback loops and inspection mechanisms. 

What’s your best advice for other engineering leaders?

  • Hire and develop the best.
  • Obsess about the customer and stakeholder management. Earn trust.
  • Always challenge assumptions and insist on high standards. 
  • Learn and be curious. 
  • Embrace humility, ownership, and empowerment.
  • Make culture and communication a priority.
  • Deliver results.

Want to hear from other engineering leaders on how they define, measure, and improve effectiveness? Read our e-book: The experts’ guide to engineering effectiveness.