Scaling Up an SE Team


In my previous post, I wrote a little bit about What makes a great SE ? My career path has involved joining smaller companies and driving through growth and expansion. This challenging path has been a very satisfying part of my job. There are unique challenges every time, but I will attempt to outline the most common scaling challenges and my point of view on how to address them.

Great companies get started with initial SEs that are true Rock Stars. I've joined several small enterprise software companies, and they tend to attract SEs that are Dave Grohl level contributors. I've had the great pleasure to know and work with some of the best in the business. You give them your software guitar, some idea about a melody, and awesome results happen. They invent the music as they start playing it. They try different things and know when it works. They have done it enough to know what to focus on, what tends to work, and they are curious learners and always listening to new music so they can incorporate the best parts of the new stuff in to what they do. If you could hire an entire team of Dave Grohl level talent, it might be amazing. But eventually you are going to need a rhythm guitar player, a drummer, and another singer or two. A great SE team will have a diversity of backgrounds, talents, cultures, and points of view. You can give them all a common understanding of the music the band will create, but they need room to bring their unique talents into the mix to make something great.

As an SE organization scales up, one of the key milestones is the installation of additional "layers" of leadership. This can take on a lot of different looks, but in general I think the approach and definition of how front line SE leaders work is absolutely critical to successfully scaling an SE organization. In general, I think flat organizations work best and these leaders will have to balance 'coaching' and 'managing'. This entire dance is very tricky in my experience. I will try to toss out a few things from my experience that happen during this growth.

  1. Where and how do we put in our first round of SE leaders ? Often you are starting from a small group of rock star individual contributors and you have to now figure out how to build the front line leader team. People that join small companies want career progression, so promotion from within is important. However, 'coaching' and 'doing' are very different skill sets. Often taking the most talented SE and asking them to coach is not the right move for individual SEs or the company. The idea of "player / coach" tends to be a common way to tackle this. In my experience, this never really works. Coaching will never be important enough to take the eye off the ball on working of a deal. You basically end up asking the most important contributors to do the biggest deals, and do some coaching during nights and weekends. I certainly like providing career progression by designating senior SEs to roles that provide deeper technical oversight to their peers, appoint them as subject matter or product experts, but this is different than the role of front line "manager". Finding the individual rock stars that also have the coaching and managing skills and interests can be tricky. Also hiring from the outside has to blend into the strategy. This can be hard as it clouds the career path for people, but I think it's critically important to add fresh eyes and experienced leaders into the mix. The other common pattern in small startups is to hire people with leadership experience as individual contributors early on. This is another great way to prepare for the future, if that plan is clear and well understood with the people you hire. So really working to identify the right members to take on this new role, and communicating to the entire team why and how you are making these decisions are really critical to keep everyone motivated and moving forward.

  2. You have to decide what you want an SE leader to really do. In organizations of any size, it is often hard to really create a unified view across the company of what you want the front line SE leaders to do. Gravity draws these leaders in a couple of directions - parachuting into big deals or pure 'HR / people managing'. I think the more clarity expressed to the entire organization about the role of the SE leader, the better chance for success. These key leaders are often the stewards of the sales motion, the key feedback loop for field info to the other parts of the company, and largely responsible for onboarding new team members. These duties need to have as much visibility (or more frankly) as the commonly understood roles of hiring, performance reviews, and territory assignment. Also, let's be honest, most SE leaders don't get the most enjoyment from performance reviews. They want to have a voice and a role in shaping the strategy and not just the care and feeding of the team.

  3. As a follow on to #2, when the organization starts to get larger and larger, the value of those front line leaders will evolve. If they are as mostly doing HR / people management their value feels is marginalized. The higher level leaders start looking at important metrics like cost of sales and suddenly those front line leaders can look overly expensive compared to the value. Once the organization gets big enough, one of the most valuable things a front line SE leader can add to the mix is bringing in new, less experienced SE talent to the team. This only works when these leaders have the time necessary to truly mentor a new hire. This is hard to invest in as a company grows, but it is so valuable. Some of the greatest SEs I have ever worked with were brought into my team as a more junior member. These people join the organization with so much energy, enthusiasm, flexibility, and passion that if you can invest the time and effort, it really pays off. As the organization grows, this idea of growing SEs instead of always having to hire rock stars becomes a critical success factor. When it comes time to do the math about the cost of management overhead, you have to include the value of having time to grow new SEs on the positive side of the calculation.

  4. The key to field sales team success is the partnership between SEs and ESMs. This same fact applies to the front line leaders. SE leaders and Sales RVP leaders have to be in very close sync. A shared sense of goals and quota and a consistent view of how all members of the team are working together is critical. I always like when comp plans, spiffs, and expectations are structured in a similar way across the technical and sales team. It can be really challenging if the goals for the ESM are measured with different metrics than the SE. The old adage that comp plans drive behavior is universal to all members of the sales team. Certainly the actual numbers and percentages will be different between SE and ESM, but the structure needs to be as consistent as reasonable. The same ideas apply to SE leaders and sales leaders. My most successful teams all included a very tight relationship between me as an SE leader, and the RVP.

  5. In almost every case, however, one of the key duties of a front line SE leader is to act as the marriage counselor between SEs and ESMs when things are not working. If you are selecting a person for the role, and can only validate one skill, this is the one. It is a very delicate task that requires a few key actions:

  • The SE leader must have a trusted relationship with all the ESMs. If the ESM does not trust you, you can't really help if things in the SE relationship goes sideways. I've had several occasions where an SE / ESM relationship has gotten bad and the ESM said "I didn't want to say anything to you, but ...". That told me I didn't do a good enough job building trust with the ESM.

  • The SE leader must regularly attend sales meetings with the team. Part of the trust from ESMs and SEs only happens when there is a consistent and regular participation in sales meetings. There is no substitute for that time spent in front of customers, driving to the airport, and sharing a meal with the team. If there becomes a challenge where the SE and ESM have a different view of the effectiveness of a meeting - you have to see it in person to be able to help.

  • When a new SE joins the team, there is always the challenge of letting them leave the nest. I would say for most of the new SE's I've ever had, there is an issue at some point where the ESM says "I'm happy to let the new SE cover my meetings, but this one is too important. I need the rock star SE I know for this one ..." This is a very tough scenario, and happens almost every time. This is where an SE leader earns their pay check. Nobody wants to risk losing a deal, but until a new SE has to fly solo in an important meeting, they can never progress and build trust with the ESM. If you have a good relationship with the ESM and the RVP, and you have a proven onboarding approach for new SE's, and you show up in meetings to understand what is needed in the real world, then you have a shot for managing through this.

  • All of this trust and interaction has to be in place when times get tough. If a team is struggling to get results, this is where unnatural acts happen, poorly qualified deals are chased, and blame may get assigned for losses. Again, a strong relationship between the SE leader and RVP is the only way to mitigate this issue. The SE leader and an RVP must come to a mutual agreement on sales motion, territory health, individual skills of both SE and ESM, and a plan for helping out. Without this, ugly things tend to happen.

So in summary, my view of the keys to scaling an SE organization:

  • Clear expectations for the SE leader role

  • Diversity in the types of SEs on the team including less experienced people when you have the coaching bandwidth

  • Strong partnership between ESM and SE as well as SE leader and RVP.

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What Makes a great SE ?