The Different Flavors of Leading PreSales Teams

Over the last five years, I’ve been the leader of three talented PreSales teams, each operating at a different size and stage of growth. Each of these teams has required me to adopt a different approach to management and leadership, which I’ve personally found to be very rewarding. I’ve never been a playbook, one-size-fits-all type of leader, so taking on new challenges has always kept me on my toes and growing while I learn.

With that said, here are some key learnings in each role.

Role 1 - Promotion Due to Team Growth

This was my first leadership opportunity, which came about due to fast growth at the company I was working for at the time. Our team size was doubling on average every 18 months, and as the summer of 2015 approached, it was clear that a single level of reporting would no longer scale.

Before being promoted into a regional role managing a team of four individual contributors, I took on increasing levels of responsibility within the team via meaty projects, which allowed me to flex my leadership chops prior to being promoted. These projects ran the gamut from designing and managing an onboarding program for new hires, to spending a month in London helping get our EMEA operations up and running, to serving as a subject matter expert overlay on regulated industry deals.

After being promoted, I went through the typical ups and downs of any new manager, and made plenty of mistakes along the way. Looking back, here are some highlights:

  • Soft Leadership - find opportunities for your team members to take on projects of their own to exhibit soft leadership within the team. Tie these projects to specific outcomes that will not only benefit the entire team, but also the person leading the project. This approach has the added benefit of allowing you to identify the next generation of leaders to help drive a promote-from-within strategy.

  • Buddy Boss - beware the “buddy boss” syndrome. This is easy to fall into, especially if you were good friends with people across the team. I don’t have a ton of great advice here other than to say be self-aware and modulate as needed. I don’t think it’s necessary to suddenly withdraw from team culture and become a stiff bureaucrat that no one likes or trusts, but by the same token, being the class clown isn’t going to be helpful either.

  • Player/Coach - be comfortable with wearing multiple hats, and not being afraid to roll up your sleeves and continue to support deals. Leading by example and teaching people how to fish are both great ways to build trust within the team. The key thing to avoid here is coming across as the “know-it-all” boss who thinks that it’s their way or the highway. I personally believe that there are many “right” ways to do something, and that my job as a coach is to help my team members find and unlock the right way for themselves.

  • First Organic Hire - this is a big milestone for any new manager. Whether it’s due to team growth or sudden attrition, being responsible for the entire hiring cycle from sourcing candidates through extending an offer is a formative experience. I recommend getting very hands-on throughout the entire hiring cycle for the first hire. This is a great way to understand the candidate pool, get really good at screening for key behavioral attributes, building an ideal candidate profile, guiding candidates through the interview process, and closing on the right candidate. I also found that by bringing my “full self” to the interview process, I was able to connect with candidates and give them a sense of what it would be like to work with me.

Role 2 - Build from Scratch

After a good 2.5 year run in my first leadership role and moving up from a regional manager to global Director, I decided it was time for a new challenge. Whenever people asked me at the time what I wanted to do next, my answer was always the same -- “take what I’ve learned in my ten years as an SE and build a team from scratch”. Fortunately, I was able to find this opportunity via my network in Austin, and I accepted a role as Director of Sales Engineering with the mandate of building out a new function and team.

Of course, as with many things in life that you spend a lot of time anticipating, reality was much different, and it started with me mourning the loss of what I had built over the last six years. In the span of one week I went from having a team of 15+ people who I valued and loved to being a lone guy with a desk and a laptop. Once I got past this initial down cycle, however, I was off to the races and quickly began ramping up across several key areas.

  • Define Team Charter & Engagement Model - if the company you find yourself at is small (sub-50), there’s a good chance a lot of folks will either not know what a Sales Engineer does, or if they do, chances are it was at a big company like Oracle or Salesforce. At the same time, the AEs will be chomping at the bit to start throwing you into the fire on every sales call. To help manage this, on week one I created a short ten slide charter and engagement model for the newly created Sales Engineering “department” (i.e. me). The document defined the purpose of the role, who the internal and external stakeholders were, and most importantly, defined when and how to engage and bring me into sales opportunities. By setting clear expectations up front, I found that it kept me focused on the sales cycle activities where I could add the most value, and more importantly, it set good habits for future AE hires.

  • Create Light Process & Systems - it’s really easy when you’re a team of one to just wing it and worry about processes and systems at a later point in time. I decided to invest time on the front end to create a framework to operate in. For example, as I onboarded myself and learned the new product, I built an onboarding spreadsheet that mapped out key milestones I achieved for each week, and aggregated product information that I was picking up. While this created extra work on my end, it made it really easy to have a ready-to-go document when I made my first hire.

  • Roll Up Your Sleeves & Do the Work - suffice to say, but a big part of being Sales Engineer #1 at a company, even with a Director title, is actually doing the work. So get ready to work on everything from RFPs, to unqualified demos, to big onsite pitches, to Infosec reviews, to everything else in between. I personally found the work to be rewarding and it gave me a good confidence boost to know that I still “had what it takes” after several years of managing and being a coach. It also allowed me to see first-hand where there were inefficiencies in the sales process, and furthermore, it allowed me to begin creating collateral and other deliverables that could be used to run repeatable plays and help the sales team scale with less effort and lift.

  • Hire As Quickly As You Can - I began making a case very early on that as a single person, there was only so much I could scale and still deliver the same impact. I decided to do this for several reasons. First, I didn’t want to become the martyr/hero SE who found himself supporting eight AEs. While I recognized that smaller venture-backed startups take on a bootstrap mentality for many functions, I also realized that the more AEs I had to support, the less effective I would be on any given deal cycle, which ultimately would lessen my impact. Second, I wanted to establish a healthy AE:SE ratio that would allow for full coverage with minimal capacity challenges and create a healthy work environment where future team members would be able to maintain some semblance of balance. I’m sure that there are some folks out there who would disagree with this approach, but my intent anytime I hire someone is that we’re on a three to four year development journey together, and in order to set that relationship up for success, it’s important to have an environment that is conducive to both growth and balance.

Role 3 - Inheriting an Existing Team

Although building a team from scratch was a rewarding experience, it also made me realize how much I missed the coaching and mentorship that comes along with leading a larger team. This is what ultimately led me to begin exploring new opportunities, and fortunately once again, my network came through for me and I landed a Director level role where I replaced a recently departed team leader. Going in, I had a fairly clear idea of what the strengths and areas of opportunity were, but it still didn’t fully prepare me for the journey ahead.

  • Watch and Observe - for me, this was an obvious starting point. No one wants to work for a blowhard who comes in on Day 1 with a playbook and self-righteous certainty that everything is wrong, or who constantly talks about how great things were at their previous company. Coming in, I decided that for the first 30 days, I would watch and observe and soak up as much information as possible. While I was happy to provide advice or offer assistance where needed, I was mostly interested in observing current processes and practices.

  • Get to Know the People - learning the product and process is all well and good, but learning about the people is ultimately what will make or break a new leader. For me, this meant not only getting to know the people on my team, but on other teams as well. This was also a first for me where I was a remote leader with a distributed team, so I over-indexed the first 4 months and made frequent trips out to HQ and other office locations. Although this may have seemed like a lot at the time, it allowed me to build solid relationships and trust within the team and across the company. And in hindsight, that decision was even more prescient due to COVID-19.

  • Add Value Along the Edges - as the new leader of an existing team that was in a period of transition when I joined, I made a decision during Week 1 to begin finding ways to add value along with the edges. For me, this meant jumping into the fray to help on Infosec reviews, which I had spent a lot of time managing in previous roles. This not only helped accelerate deals, but also freed up countless hours of time for my team members so they could focus on the areas of the sales cycle where they could drive the biggest impact.

  • Create Shared Ownership - heading into the second quarter of my tenure, I decided to create MBO projects designed to bolster team operations and efficiency. Rather than force projects on people, I set some broad parameters and guidelines around what I was hoping we would accomplish, and then had individual team members pick passion projects that would drive these outcomes. The end result was that everyone completed their projects, and we now have much better systems and processes in place, including a formal onboarding curriculum, an enhanced RFP database, and better enablement around major project releases.

  • Amplify What Works, Toss What Doesn’t - there comes a point when an inherited team becomes your team and everything that comes along with it. Six months in, I have identified what’s been working well, and what hasn’t, so we’re now at the point where we’re doubling down on successful strategies, and tossing out everything that wasn’t working or was just mediocre. As I’ve told several team members over the last few weeks, I’d rather our team do ten things really well instead of twenty things just so-so. As a result of this focus, this has freed up more time to support Stage 2 and Stage 3 sales cycle activities where we can drive the biggest impact.

In closing, the last five years as a PreSales leader have been quite the journey, but I wouldn’t trade a minute of it. I’ve had the privilege of working with very talented, passionate, and collaborative individuals, and have had the pleasure of seeing each of them grow in their own careers. And for me, at the end of the day, that has been much more rewarding and fulfilling than winning another deal.

Chris is a highly accomplished PreSales leader with 15 years of experience building, scaling, and leading teams in competitive enterprise SaaS markets. He is currently Director of Solutions Consulting at Dynamic Signal.

Connect with Chris on LinkedIn.

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The Leadership collective is a group designed for PreSales leaders in a management capacity (Manager+ title) who are looking to network, grow professionally, and actively participate.

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