Vertex Ventures IL
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Vertex Ventures IL

Get to know your design partner: Lemonade’s VP R&D Erez Dickman

Local partners and champions can help you, entrepreneurs and early-stage startups, when you are building your product and attempting to penetrate the market. At Vertex Ventures we’re on a mission to help, so we’re publishing a series of interviews with these Israeli executives, including valuable tips and insights. This is the third post of the series, featuring Lemonade’s VP R&D: Erez Dickman. You can read the previous posts with JFrog’s VP R&D here, Rapyd’s CISO, here.

8 Insights From the Field for Dev Tools and Engineering Entrepreneurs

Lemonade is considered a loveable brand and one of the company’s main missions is to connect all its employees to that idea. As VP R&D, Erez Dickman focuses a lot of his attention on his employees and connecting them to the company culture, while maintaining productivity. As you’ll see, he invests a lot of time in finding the right tools and methods to ensure his people are recruited, onboarded and managed in a constructive way. At the same time, he’s looking for solutions for answering the most cutting-edge technological challenges of today.

1. What is your top priority as VP R&D right now?

My top priority has always been and probably always will be hiring and retaining top talent. As the company grows exponentially, we are looking to fill a variety of roles, and I’m always looking at both the present and the future. We need to make sure we are building a strong foundation with the right people — today and going forward.

Employees are the key to any progress we make at Lemonade. We strongly believe in bottom up growth within our team, so many new managerial positions are filled by our team members. That said, we look to also bring on people with new perspectives and diverse experiences. We want to have a mixture of internal and external skills and experience, because it creates a good combination.

Today, we are more open to external hiring of leadership roles. When looking at the strategic needs our teams have, we’re comfortable with and even looking to hire someone who can bring the exact know-how from outside. We need someone who has already built these types of teams. Once we find these leaders, we give them the responsibility to build the strategy and future plan of their team.

We have quite a clear vision of where we’re going to be a year from now, business and product-wise. We can determine our future hiring needs based on that. This is obviously not a clear-cut process, and we will continue to adapt to changing needs.

2. Which tools and methods do you use for continuous improvement in the R&D team?

Culture is just as important as productivity, and one of the most important tenets of our company culture is being straightforward: We keep it real, direct, and to the point. We expect each manager (team leader and up) to be connected to their team and to be able to reflect what is going on, how and whether people are motivated, and any issues that may arise in the future.

We also use tools that can support these values. We use Officevibe so people can share their thoughts in an anonymous way, and management can receive constructive feedback. It allows quantitative and anonymous feedback that can be translated into action items of improvement.

From a process perspective, we focus on iterative progress based on constantly delivering value and measuring what does and does not work. It is easier to improve in short iterations, through small changes, and by constantly measuring impact.

When it comes to improvements, I think there isn’t one clear way to measure velocity or other KPIs that are supposedly related to improvements. We can measure multiple metrics that, when aggregated, can steer us in the right direction. For example, the share of time the team spends on fixing bugs, the number of rollbacks, the number of failed customer interactions, our sprint content, and more. All of these KPIs together, and many others, can monitor the team’s “health” over time. Using them in an incremental and aggregative process really helps us to keep observing and seeing how the previous week was, what worked well and what didn’t.

In addition, we work with a tool called to manage our 1:1 interactions. It provides visibility into topics that are about to be discussed so participants can prepare and follow up easily.

Finally, there’s the question of workforce management. We still haven’t found a tool that can actually address the ongoing management needs of modern teams. We’re structured both vertically according to linear management and horizontally according to functional expertise, so employees often have two different groups to which to relate.

We are automation geeks so we built an internal tool to reflect that. Based on its content we can plan ahead, manage versions and releases, manage budgets, message each other and get notifications. For example, one of the hardest things for a fast-growing team is finding a solution for decision sharing. With our tool, we try to balance between over communication and no communication automatically.

3. How do you overcome onboarding challenges and gaps?

Our main goal and challenge is to find the best way to connect new employees to the company’s culture and vibe. This need was especially significant when everyone was working remotely. One method that dramatically improved this was adding conversational steps to the hiring process. They weren’t actual interviews, but rather meetings to allow both sides to get to know each other better. Once we added them, we dramatically improved our ability to convince people to take a leap of faith and join us. The relationship and the connection going forward improved as well.

Moreover, since different candidates have different personal preferences, we are very flexible with our recruitment process. We allow candidates to decide whether they want to conduct a face to face interview or to complete an offline exercise first, to reduce the stress that accompanies a real time observation. Some candidates prefer to work on the exercise during the interview, which works for us as well. So flexibility is an essential ingredient in our process. We understand that different people have different needs, and we adapt our processes accordingly.

For onboarding, we have a dedicated team at Lemonade whose mission is to prepare and run the best onboarding process for new employees. This team creates an adjusted process that allows new employees to onboard based on their experience and future challenges. During Covid this was effective, since it framed the process and also, by definition, created a group of people with whom new employees could relate. The team is focused solely on onboarding, mentorship and coaching, because of how important that process is. As we gain more experience, we keep improving the team’s processes.

4. What are the main challenges of cloud development today?

We are a 100% cloud-native company that resides almost exclusively on Amazon.

The main challenge we face today with cloud environments is managing security while providing a seamless developer experience for our team. Specifically, monitoring potential weaknesses and prioritizing the work plan, so we can map and manage the risks.

Many companies today are able to analyze vulnerabilities in your cloud environment and they can also help mitigate them. We are trying to work with as many vendors who can bring us value quickly as they can. Many of them are based in Israel. Yet, we’re still missing a single vendor who can identify and prioritize all issues.

In both domains, it’s hard to distinguish signal from noise; Not a day goes by without receiving emails or phone calls from vendors that claim to have solved these problems. I think vendors can do a better job of differentiating themselves and being more succinct about their USPs.

5. Where are the main quality challenges in the development lifecycle?

It’s a combination of many factors. At Lemonade we are very customer-centric, so things don’t only need to function without bugs; they need to make for a delightful user experience. We aim to continuously create new value to our customers. To achieve this, we have quality engineers who oversee the UX and customer experience.

In addition, good automation is an important foundation for productive dev teams. As the product and environment complexity evolves, the complexity of introducing changes increases dramatically. Therefore, once a feature becomes stable, we automate its testing.

A recent trend that we are experimenting with is leveraging tools that allow non-developers to build test automation. Tools like for web development or for mobile native allow the QA team to concentrate on testing the business KPIs, rather than typing out tests.

That being said, there is always room for improvement both in manual testing and in automation.

6. How do you handle production incidents like resolution, insights and retro, and what is still missing?

When it comes to incident management, we spoke with many companies whose needs are similar to ours. However, we haven’t found the exact tool that meets our specific requirements, yet.

We are looking for tools that allow our employees to be notified and regularly updated about the status of the incident. There are companies that do a great job communicating the status of incidents to customers. Transparency and visibility are important to us so we’d like to be able to communicate efficiently to the right people.

I often find that internal tools that help us meet our exact needs are not difficult to build in-house. Our internal ecosystem is filled with automations that we built on top of our Slack bot platform, Cooper. It even allows us to reflect our culture and build our desired work process in a better way. To achieve that, we have a team responsible for internal tools development.

For incidents, for example, we have a team that builds our internal incident management, using Slack as a hub. It is easy to create workflows in Slack, so we used this capability to reflect our business logic and internal flows. This internal tool also enables integration with other tools we use, which meets our visibility and monitoring needs. We work with PagerDuty for task management, DataDog, and many other platforms. Each one answers a specific question, so we unified them within Slack. This allows us to gain relevant transparency and adjust workflows.

7. What is R&D’s ownership in regards to security?

I have been approached by many new startups that address security needs. We pay close attention to security and work closely with our amazing CISO to evaluate and provide feedback. We run many pilots, and some design partnerships. If we find something that gives us value, we are ready to start using it and paying for it.

The application security engineer is an important role in an engineering team. This person should be a strong developer with a great security understanding. He or she is responsible for finding the right tool to answer the app security requirements.

The security tools our development team chooses are influenced by our technological needs. For example, because we have a mobile app, we need mobile app security tools.

Beyond tools, the product’s architecture and our user and service authentication and authorization are important aspects of our platform’s security. They can become complex and the existing solutions out there are quite expensive so many companies can’t afford to use them.

I believe there is an opportunity to provide cost effective authentication & authorization tools that are more fitting for early stage startups and can eliminate the pain of implementing in-house solutions which are often vulnerable.

8. How can a founder convince you to partner with her/him as a design partner?

Don’t pressure us; Don’t be an aggressive salesperson. If you work with other companies, mention that. It helps us gain trust. If the product is low-friction and we can start out for free or for a low price, this will also speed up the process.

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