The VP Engineering Challenges During Hyper-Growth and the Engineering Operations as Their Right Hand Complementary: Part 1 — The Team Building and HR Challenge

The position of VP of Engineering is one of the most challenging roles, especially in the hyper-growth stage of the company. The Engineering VPs are usually in charge of the largest and most resource-intensive group in the company. Their main challenge is to create something entirely new. This often encounters a variety of challenges and it all happens under great time pressure, like building an airplane while flying.

This article is the first part of a series about the challenges faced by the VP of Engineering during the hyper-growth phase. I’ve interviewed Hemdat Cohen Shraga, an experienced VP of Engineering, who has contributed to several companies during their hyper-growth stages throughout her career. Her professional journey includes Cybereason, Finastra, Matomy, and is currently serving as the VP of Engineering at Priority. Though Priority is not a classical hyper-growth startup, it is indeed going through a huge metamorphosis moving forward.

In this article series, Hemdat offers valuable insights, shedding light on the primary challenges VPs of Engineering face across four main areas:

1. Human Resources and Team Building

2. Business Strategy and Operations

3. Technological

4. Process Development and Optimization.

Each challenge demands a thorough understanding of being able to see the vision and our end goal while being able to plan and execute the steps toward it. Each will be explored in full detail in a dedicated article. In this series, we will delve into how Engineering Operations can serve as the complementary partner to the VP of Engineering, communicate the vision top-down to team members, and provide the VP of Engineering practical insights and a closer understanding of on-the-ground realities, bottom-up.

As each challenge is built from multiple challenges, we’ve split the article to contain one challenge in depth each time.

HR Challenge — Building the Team

When joining a startup as a VP of Engineering, it’s usually when the startup has already hit the glass ceiling it’s trying to break and pass. At this stage, usually, the team understands they need a dramatic change, but it’s very hard to accept the changes needed. Also on the personal level, many of the people have reached their own glass ceiling — they became managers with no prior experience, or became managers of very large teams with a lot of cross-team dependencies, or have become architects of a huge system that requires a whole new level of expertise. Many times the solution includes bringing more senior people and decreasing the control rod. While many look at this as a position reduction, this in fact is the only healthy way for the startup to scale.

Let’s start breaking down the challenges.

Deciding on the Right Structure

Sometimes the Engineering department reaches a glass ceiling: The velocity declines, the onboarding of new people takes forever, and the amount of communication in order to make a minor decision feels too damn high.One of the most effective ways to see how to increase the velocity and improve current impediments is by reviewing the Engineering department structure. As we usually begin our startup journey with technology-oriented teams, we need to stop and ask ourselves — is it still the right structure for us? As the structure will affect every aspect of the Engineering way of working, making this kind of change might create a shock for the department while it could be beneficial and solve many pain points.

When discussing this question there are multiple aspects to consider: Should we move from disciplinary teams to multidisciplinary teams, which are product-oriented? Another business aspect to consider — usually there’s a legacy product — should we consider dividing our teams into New Products and Legacy products? This will increase our deeper understanding and easier onboarding for each product but also might bring less flexibility in development tasks between people. Another question that comes to mind is the separation between the new features and supporting our customers, as the business wants a higher pace in receiving more and more new features vs customer requests of fixing known bugs that get in the way of crucial usage of the product.

The answers to these questions imply significantly in every other HR aspect — what type of managers do we need, and how much information do we need to teach every new employee? How and which technical background do we need? How senior should they be? For example, if our goal is to form squads — multidisciplinary teams — then our focus must be on individuals with strong technological backgrounds and experts who can lead their professional domains within the squad. Conversely, if we lean towards technology-oriented teams, the management’s emphasis shifts towards a more project-oriented approach, aiming to construct a cohesive big picture across teams.

The exact structure of the teams is based on the organizational logic and needs. For example in a web-based company, maybe we’ll need more than one UX/UI member per team and have them in all teams. In a more backend, tech-savvy team, there might be a reduced need for such a member. For a multidisciplinary team, another question is who’s the tech lead of the team? Should it be a more backend-oriented person or a full stack? In a multidisciplinary team, it will usually be the tech lead that represents the most relevant background. E.g, a team called “Server Platform” would probably be led by a Backend oriented team lead, and other solutions should be picked to help them overcome the gap in the other disciplines profession.

For instance, in a cybersecurity company I worked with, the teams were technology-oriented, hence every new feature decision required experts from each of the four disciplinary teams. This approach isn’t scalable. Hence, when structuring teams, we’ve moved into product-oriented teams, where each team has reached its own unique expertise. When structuring it, It was essential to empower them with complete autonomy over each component, enabling them to progress independently.

Once the right structure is decided and announced, then starts the real challenge of moving the parts and making it work. In each new structure, there’s a need to define the new roles more precisely and implement down-to-earth processes that will allow the organizational structure to fill in its targets.

This interesting challenge affects most of all — our current team members and their motivation and dedication to the scaling startup, as you’ll see in our next challenge to be elaborated.

Engineering Operations Contribution:

The Engineering Operations work starts even before the restructuring. As part of laying the ground for a better structure, we need to collect information regarding the current status of our people: how many people we currently have from each discipline, who has a strong technical and management background, etc. Also, we need to understand the current features’ status: Which teams are usually dependent on one another? Why are they dependent on one another and what options could solve this dependency? These answers can change or get better answers based on reports and prior data from past feature experience.

Once the organizational structure is communicated, the real challenge begins- making it work; defining new roles, and translating them into practical processes and tools in a way that the organization can achieve its objectives. Processes could include updated planning processes, and better guild-based consulting (e.g. if a back-end team lead has to lead now also the front-end side, they’ll need professional guidance). Communication methods have to improve, so management is kept updated and architectural decisions are kept aligned. All tools have to reflect the new structure and updated processes, allowing a cross-teams clear cross-team view and the ability to produce the relevant dashboards for status and red flags.

Building the Management Team

As we’re planning for the startup growth, and aiming for a new structure that will best support the challenges, a key factor is its current team members and leads and their expectations and preferences. As the startup grows, the need for fast delivery is prominent, and scaling the team becomes imperative. So how do you do it?

The first step is to analyze the people you have — a complex matrix of who’s technologically strong and/or a good manager, along with their seniority and specific background. Then we need to build a structure that would both be effective for the company’s growth stage and applicable to the current team.

In order to achieve the right structure with the right positioning, The key strategy involves conducting meetings with all essential team members to grasp their perspectives and backgrounds. These sessions also serve as opportunities for personal coaching and reflection, guiding individuals to recognize their paradigms and evaluate their contribution to personal development. Some individuals might believe they are destined for management roles, when in fact their strengths are better suited to technical leadership. The opposite also happens: convincing someone with a very strong technical background to take a lead role to all the new team members, in order to bring their expertise to the team. Part of the challenge is to persuade the founders and team members who have been there from the beginning and might resist the change the most. In a very delicate balance- we want to encourage them to be a part of the change and maybe even lead it.

The second step, after the company has established the updated structure, for example, squads or tribes, and has understood the current situation in terms of current leads and expecting leads, the next phase is to create some kind of hierarchy by introducing directors / Group managers. Until this stage the organization operated with a flat structure, where the VP of Engineering directly interacts with the team, making it easy to identify what works and what doesn’t. As we expand, the teams grow very large and we need to break them into smaller teams, usually by adding another layer in the hierarchy. We aim for the group managers that will manage the squads distancing the VP of Engineering from the daily tasks of developers.

Integrating new directors into a smaller organization can present a significant challenge. Typically, these are highly experienced managers from outside the company, as the company has multiple technology professionals, but lacks more experienced managers. Striking the right balance between preserving the existing company culture and leveraging their extensive prior experience is a complex task.

At this point, in order to keep the velocity and a functional structure, we need to decentralize the control and provide autonomy. The VP of Engineering must adapt to a decentralized approach, focusing on identifying red flags and maintaining the effectiveness of the engineering department without getting into the details.

Engineering Operations Contribution:

Engineering Operations, work very closely with the directors level and their teams: They work on a day-to-day basis with all the teams in each group, understanding thoroughly the teams’ culture, product’ and processes. Then they communicate and can sync between the teams and their inter-team dependencies effectively. Moreover, as they work with multiple directors (or a small group of Engineering Ops does), they can oversee the gaps between the groups in processes, tools, and data insights, providing them the advantage of

• Identify both similarities and differences between teams and offer improvement points.
• Provide key insights to accurately translate and implement company and engineering OKRs across teams.

Recruiting and Onboarding Many People at Once

After we’ve dealt in prior stages with the right structure for scale, we can translate the new organizational structure into a Recruitment and onboarding plan. These introduce different challenges, as we’ll now whare.

Recruitment encompasses 3 main focus challenges:

• Finding the right people — Each team member is crucial for creating the right team and atmosphere and finding the right person (on the right budget!) for the organization consumes a lot of time while the tools we currently have to find the right matching are scarce. Things that we need to take into consideration are — what is the right seniority for the role and how much relevant experience and or business background? Adjusting to the team’s culture is also key to a good onboarding experience.
• Keeping the right recruitment plan for each team — Finding the right balance between the team needs for new team members and the team’s ability to onboard. For each tribe and team we need to consider the current team capacity — is there someone who can now be in charge of onboarding a new team member or should we wait and let the prior ones blend in first? Are there any teams where their knowledge is vast and onboarding takes longer? According to these questions, the right recruitment and onboarding project and timeline will be most effective.
• Keeping the balance between needs and budget- A clear budget is key for working within boundaries. As we plan for recruiting more and more people we need to decide on the right balance between specific talents and the need for multiple recruitments.

Onboarding many new employees at once presents 3 main challenges:

• Time and Infrastructure: Onboarding a large number of new hires significantly diverts time away from primary work tasks and requires solid technological infrastructure and thorough documentation, which are typically lacking at this stage, making the process more challenging and time-consuming.
• Project-Managed Onboarding: The process of integrating many new employees simultaneously demands organization similar to project management, ensuring each individual promptly receives the necessary resources, attention, and equipment.
• Culture — With a rapid influx of new team members, maintaining the company’s culture and values becomes a challenge, as these newcomers quickly constitute a significant portion of the organization.

With all of this in mind, It’s important to have the right balance. Consider the analogy of making soup: you can’t simply combine the vegetables with water and expect a flavorful result. Instead, it requires the precise blending of ingredients. Similarly, in our team dynamics, it’s essential to distribute roles effectively and assemble the right mix of people in each team. This blend should ideally encompass a blend of technology skills, innovative ideas, and management capabilities to achieve the best outcomes.

Engineering Operations Contribution

As we’ve mentioned above, recruitment and especially onboarding are both very time-consuming actions. Engineering operations can help manage the recruitment and onboarding processes as a project. Also, managing projects that will shorten and make the onboarding process more effective could be a key project in Engineering Management.

In conclusion, In this part of the series of articles, we’ve touched on the main people-oriented challenges, starting from finding the best structure fitting the company’s growth and from there on — the recruitment process, onboarding effectively after, and building the management team.

Our next article will focus on the Business challenge and how we are building the best fitting product balanced between all the product stakeholders — and we’re not just talking about clients here :)