Zooming Out From Engineering – Square Corner Blog – Medium


As originally seen on Greylock Partners’ blog, here are some insights on leadership, career development, and building teams at scale that Square’s Head of Seller, Alyssa Henry, shared during the 2019 SFELC Summit.

Square’s Head of Seller & Developer Business Units & Infrastructure Engineering, Alyssa Henry

Leading an organization of 10 employees is considerably different than leading an organization of 10,000+ employees. As teams increase and communication becomes more challenging, a lot can break down. In this episode of Greymatter, we share a fireside discussion from the 2019 SFELC Summit on building and managing scaling teams. NodeSource VP of Engineering, Chanda Dharap talks with Square’s Head of Seller & Developer Business Units & Infrastructure Engineering, Alyssa Henry. Alyssa shares lessons from scaling companies at hyper-scale including Square and AWS, how to bring purpose to your employee’s work, and advice for building company culture.

Alyssa leads Square’s cross functional teams with P&L responsibility and is working to shift Square from an app focused on payment processing to a broad financial services platform and commerce ecosystem. Prior, she led AWS Storage Services including Amazon Simple Storage Service and Amazon Glacier where she was responsible for software development and operations. Earlier in her career, Alyssa held several roles in program and product management at Microsoft.

SFELC is a curated community of 2500+ engineering leaders evolving the way leadership is implemented in the tech industry. Greylock Partners is the VC partner for SFELC, and sponsored the annual SFELC Summit which hosted top industry leaders to share management best practices and leadership advice.

Below is an edited transcript of key points from Dan and Aditya’s fireside discussion.

Bring Purpose To Your Team’s Work

“People want to work on something that matters, something that allows them to grow and learn. As a leader and as a manager, you should constantly determine how to ensure the people on your team have sufficient autonomy, mastery, and purpose in their work. You want to make sure that they’re engaged and love what they’re doing and sometimes that involves pushing your employees to grow further. It’s understanding how to align the required work with the employee’s interests to bring greater purpose to their work.”- Alyssa Henry

Build Company Culture Through Collaboration

“Ultimately the best culture comes from hiring managers and employees that want to be involved with all aspects of building your company’s culture. How do you enable people within the team to help you build not only the product and the code, but also help build the team from a culture perspective? A hiring bar needs to be established and adhered to across the company.

At Square, we brought employees together from across different teams within the company to define what culture should look like. From there, we internally established what the engineering career development and ladders looks like. I believe that as much as you can get a broad range of people with a broad range of perspectives to collaborate together, you can build something great where you’re building both the company and the team, not just building the code.”- Alyssa Henry

Leaders Are Constantly Learning

“When I first started my career, I worked with teams that had been doing the same thing for 20 years and they never understood that they were rapidly becoming obsolete. I learned early on that in the technology industry especially, bad things can happen if you don’t stay current. Constantly learning is critical. You can learn from everyone around you. I always encourage my team to seek out the people who have the skills in the areas they want to learn and meet regularly. As a manager, hire people that can help teach you and then provide them the space to do that and respect the skill sets that they bring.”- Alyssa Henry

At What Level of Scale Should Product And Engineering Be in the Same Organization?

“At some level, they’re always in the same organization, because it’s the same company. It’s just a matter of determining at what point they meet within the hierarchy of a company, and I think it depends. If your company has one and only one product and everyone’s working on the same thing, most likely they’ll meet at the C-level underneath the CEO, CTO or a CPO.

Because everyone’s working on one thing and the CEO is, in effect, the general manager for the product overall. In a business like Square or AWS where there’s a large amount of products and individual businesses product and engineering were organized with more of a general management structure where you push that down the organization so you get product and engineering coming together lowered down the organization which just helps you move faster and reduces the organizational distance between those two functions for the product.”- Alyssa Henry

Lessons From Hyper-scale

“Growing is always fun, but challenging. The way to grow an organization is similar to the way to grow a code base. Whether it’s a monolith organization or monolith code base, you constantly figure out how to do cell divide, how to decompose or break apart so that you can get stronger boundaries and the ability to iterate in a way that you can make changes that don’t ripple through everything else so that you can reason about them independently” – Alyssa Henry



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