Evaluating a Sales Role: Board & Executive Team
The most important part of any career-changing decision is the evaluation of the team you are going to work with. The product, salary, office, sales process, etc don’t mean much if you’re not working with a group of people you jive with, and part of a larger ecosystem that reflects your values. Too often, especially in sales, we make a judgement on the team based on a series of 20-minute conversations with 5 or 6 people. Although useful, this can be insufficient in making a determination as interviewers are generally trained to sell you on joining. To make a smart judgement you have to break apart the team and look at each section individually. Those sections are 1) board & execs 2) department leadership 3) direct manager and 4) peer group. This post will focus on the board & execs and chain of command.
Board & Execs
Unless you are joining a company very early it’s unlikely you will meet a member of the board or executive suite. Therefore, we have to consider signalling in evaluating this group of people. Those signals are values & power. If you were enlisting in the military this group of people would be equivalent to the “nation” you represented. You probably wouldn’t enlist if you didn’t align with the values of the country or believe you had a reasonable chance of winning the war. The same is true of organizational leadership.
In order to make a determination on values, you will have to do some homework. Starting with the board, you can read up on their investment firms, what types of investments they make, and any philanthropic endeavours they’ve contributed to. Looking into other companies they are involved with is also a good exercise, as is a quick google search of the persons name. The executive team is different. You should still look these folks up, understand their backgrounds, and specifically try and get insight into the types of people they hire, but since your interview panel will have interacted with them, you can generally learn a lot that way. This is just my opinion but I believe values stem from having a thesis on customer experience, employee experience, innovation, work-life integration, & inclusivity. This isn’t perfect, but I believe you can suss these out through five questions:
1) To your knowledge, what was the worst situation this company has had with a customer, and how did the team handle it?
2) What was the last crisis or major problem your company went through? Can you talk me through everything that happened & how leadership communicated?
3) What is the biggest idea the company is pursuing right now?
4) What time does the leadership team go home?
5) Can you provide an example of a recent initiative the company took to foster a more inclusive workplace or bring more diverse viewpoints to the table?
Power is a little bit easier to assess and is the sum of knowledge & resource availability on the company subject matter. At the board level, power comes from the availability to provide follow on capital or facilitate follow on capital, make strong introductions, & provide a viewpoint that is useful to the business. Run through Crunchbase to understand the history of these people & their firms, how big their funds are, how many investments they’ve made, and the outcomes of their investments. On the executive side, you are looking for either relevant experience or a history of value creation. Relevant experience is easy to figure out - have these people done things in their past that gives them a unique advantage in this business? Value creation is a little more nebulous but the definition is whether these people have a history of leaving things better than they find them. Personally, I’d rather work for someone who hustled through college to make a small business more profitable than someone who did nothing but went to Harvard. Experience & value creation is more important in determining power than pedigree.
The next layer of evaluation happens at the department level. I would define this as your VP of Sales & any directors who aren’t frontline managers. When thinking about the chain of command there are surface-level things such as trust & respect that are incredibly important, but digging deeper you want to try and predict the types of decisions these people will make, as they will generally have authority over the structure of your role. SaaStr has a great read on this but there are four types of sales leaders: the evangelist, the dashboarder, the go-big, & the repeatability expert. In short, the definitions:
Evangelist: Fun, deep into the product subject matter, wants to be on the phone with customers. Known for micro-decisions every time they hear something on the phone.
Dashboarder: Analytical, looks at data all day, can provide good insights based on said data. Known for never speaking to the team but posting screenshots of dashboards in slack.
Go-big: Visionary, thinking deeply about scale, and the opportunities to find leverage in the business. Known for putting the team at the focal point of growth.
Repeatability: Solutions-oriented, working to take early-stage learnings & turn them into processes. Known for making sales reps lives easier & helping them make more money.
You should only work on a team led by a go-big or repeatability expert. This is not to say the evangelist & the dashboarder don’t bring great qualities to the table, but they are the polarized ends of the spectrum, and therefore will make polarizing decisions. Great questions to ask to determine what type of leader(s) are running the team:
1) How does the VP of Sales or director interact with the team?
2) How often do you see or hear from sales leadership?
Things to watch out for are incredibly high visibility & lurking on every call (evangelist), or incredibly low visibility & only talking about data in company meetings (dashboarder)
To summarize, when evaluating the board & exec team you are looking for values alignment & power - will they build an organization you are proud to be a part of, and if things get tough, is there a pool of resources to tap into. When evaluating your department leaders, you are looking to predict what types of decisions they will make - are they an evangelist/dashboarder or a go-big/repeatability expert. In the next post we’ll dive into how to evaluate your direct manager & peer group.
Have a great weekend