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Career Life Stories: Connor Fee, Winning by Design

Connor Fee was a successful Chief Revenue Officer (CRO) before becoming a partner at Winning by Design, and now works with high-growth SaaS and B2B companies to drive revenue growth. He talks to us about his science-driven approach to sales and customer success, what’s the difference between a CRO and VP of Sales, and the best ways to get your start if you want to be a CRO.

With a degree in Systems and Information Engineering, how did you evolve into a Chief Revenue Officer?

About half of my graduating class, including me, went into consulting. The particular engineering discipline I was in focused heavily on taking big problems and breaking them down into smaller ones, which turned out to be great preparation for strategy consulting. I really didn’t start getting into sales and marketing until after I left consulting and started my own startup. I got into sales and marketing out of necessity more than desire. It just so happened that we fell into creating a b2b media company and somebody had to sell it. I sure as heck couldn’t build it, so it became my job to get out in front of customers.

Connor Fee

There was a VP of Sales at another tech company who I admired and I asked him to be my mentor. I told him I felt somewhat smarmy doing sales, and he encouraged me to reframe my thinking. He told me my job was to go out and find customers to whom I could provide far more value than they were going to pay me for. That made a lot of sense to me and it felt like something I could deliver. It’s since become the cornerstone of my sales mindset. Find people that you can provide an incredible amount of value to, and then charge them for some portion of that value.

Can you characterize your role as CRO? How does it differ from that of a VP of Sales?

I don’t know that the market is mature enough to answer this question well. Often, a CRO is more of a VP of Sales who wants a C-level title because marketing or customer success got one.

At a general level, there are two types of VPs of Sales. Some are more of your prototypical hunters, getting the large late-quarter deals over the line. These folks are often very senior and critically important members of the executive team, but operate more like seasoned individual contributors. Other VPs of Sales are more process-driven and scale-oriented, who may have come from a sales operations or business operations background. You see both styles in companies big and small.

It’s my belief that a good CRO should be responsible for the entire revenue funnel – marketing, sales and customer success. By that I mean educating customers, winning customers and growing customer numbers. I think a successful CRO looks a little bit more like the process-driven, systems-oriented VP of Sales combined with a VP of Marketing, rather than an alpha-hunter.

What does it mean to be a process-driven CRO?

A good CRO is looking at the entire revenue funnel. How do marketing and sales function together? The sales analysis can get incredibly complex – much more so than simply calculating how many calls the team should make in order to land a certain number of meetings.

For example, we might notice that the marketing prospect-to-MQL conversion is low. We need to figure out why that is and what we’re going to do about it. That requires an understanding about the various marketing channels at play. Investigation may uncover that the low MQL ratio is not a problem because the MQL to SQL number is up because you’re getting fewer, but higher quality leads. If you don’t look at the entire problem as an integrated system, then you could inadvertently try to “fix” something like a low prospect-to-MQL ratio that doesn’t need to be fixed.

In your opinion, what is the most difficult position in the sales and marketing revenue funnel to hire?

Junior and mid-level sales professionals get easier to hire over time because it’s a repeat hiring process – the territory may be different, but the role itself is the same. Marketing is tricky because each functional role is unique. A product marketer is different to a demand generation marketer is different to a PR person.

The VP of Sales role has the potential to be one of the most difficult to hire, but it depends on the type of sales leader you’re looking for. There are a lot of great Directors of Sales out there that aspire to be VPs of Sales. If you’re willing to give away titles, then it gets a little easier to hire. If the profile you’re after is akin to a seasoned, high-performing individual contributor that’s great at hunting and closing big deals, then again, it’s not as hard as you might imagine. Hiring becomes a lot more difficult when you’re looking for a scale and process-oriented VP of Sales who can be a peer and partner to the rest of the executive team.

How important is it for a startup to hire a VP of Sales who has scaled at the level they want their company to scale (e.g. a VP of sales who as scaled beyond [X]MM in revenue)?

There is an opinion in the industry that if you haven’t done it before, you don’t know how to do it. I think that’s completely absurd. Really good candidates don’t stick around or seek out opportunities to do the same thing over and over. Wouldn’t you prefer to hire a candidate that’s hungry and up for a challenge? The implication that people are capable of doing only the things they’ve done before bothers me.

In that same breath, I spoke with another CRO of whom I’m a big fan, and his perspective on this was pretty interesting. He told me that he needed a Head of Marketing, a Head of Customer success and a VP of Sales. In two of those departments, he wanted someone who had “been there, done that” because he didn’t want to be teaching them the discipline. In the remaining seat, he wanted to put a very strong up-and-comer, because he knew that the potential of that individual was incredibly high if he could get them over some of the learning that they haven’t experienced yet. I loved the perspective that he was striving to achieve, which was balance across the team.

What is one question you always ask candidates in an interview, and what does it tell you about them?

I like to hire candidates who fall a little bit outside the norm on the “range vs experience” spectrum. I look for individuals who have the appetite and aptitude for doing things outside of what they’ve already done before (range) and yet who also have a fair amount of domain expertise (experience).

There are plenty of people who have lots of experience that make great Directors of Content Marketing, for example, but you’re not going to get a whole lot of range out of them. Similarly, there are plenty of people who are young and smart and capable with lots of range but very little experience.

If I ask a demand generation professional to tell me about how they run their marketing channels, lots of people give very good, yet familiar, answers to that question. Occasionally, you get that candidate who tells you about how they used to do it, how they do it now, what they think is wrong with the current way of doing things, and how they think it should be done moving forward. That person is demonstrating a capacity for thinking beyond their immediate context, revealing both experience and range.

I like to ask people about the last book they read or the coolest thing they’ve learned in the last month. I look for people who have learned or read things wildly outside their scope of work. Intellectual curiosity is a good proxy for range. Plus, people like to be around and work with people who are interesting and can converse on topics beyond their domain of expertise.

What advice do you have for young professionals looking to become a CRO? Are there any key developmental roles you’d recommend for them to seek out?

First of all, sales is not a discipline where we do a good job of teaching people how to be much more than an individual contributor or a front line manager. To progress to a relatively senior role , you have to either be a alpha-hunter/closer, or you really have to expose yourself to areas of the business that make you a little uncomfortable. You should wallow in the uncomfortable for a while; I’ve never once taken a job where the first four months I didn’t feel like a total imposter.

Secondly, I think it’s impossible to know what the job of a CRO is until you get there. My advice would be to go and sit down with people who do the job and make sure that it’s what you want to do as opposed to just the next job up the chain that looks or sounds good.

There are a lot of phenomenal sales people who are convinced they want to be managers but have absolutely no business being in management. Should you find that management is not what you want to do, my advice is to try to find an organization that values high-performing individual contributors.

A successful CRO sees the bigger picture, meaning they have had broad business exposure and have spent time thinking about systems, processes and even, to some extent, math and engineering. In terms of development, I would definitely encourage aspiring CROs to befriend the engineers in your organization – understand the way they think and solve problems. Find yourself in situations where math and process becomes a critical part of what you’re doing. Sit down with your team and evaluate the existing process – ask yourself, did we get to this process intentionally or by accident?

How do you coach your team to manage the stress associated with the ups and downs of a career in sales? What tactics have you’ve adopted to stay motivated and prevent burnout?

I think it’s unfair to say that sales is more stressful than other functions. In a well-run organization, everyone should have clear and measurable goals. Typically, we think of sales as more stressful because you either make your goal or you don’t and so much of your compensation is tied to it. Everyone, no matter the discipline, should have goals that are that well-defined.

Often, circumstances are more stressful when they are surprising. If I can see that a member of my team doesn’t have the pipeline to make their target, we should be having a conversation sooner rather than later.

I think that many people’s consternation at work or in relationships comes from mismanaged expectations, so it’s my job to make the situation as straightforward as possible. Let’s not over-react in the moment. Is there anything we can do about this quarter to impact the outcome in a meaningful way? If not, let’s focus all of our energy on improving processes for next quarter.

The other thing that I coach my team on is to acknowledge what’s in their control versus what’s not in their control – let’s face it, there are a lot of things out of our control.

I encourage my team to stay in front of the information and manage up. If you know half-way through the quarter that you’re going to miss your target, communicate that to your boss so you can work on it together. Once you get a handle on the things you can control, you start to see people’s stress come down.

What sales or leadership related resources (blogs, books, podcasts, conferences, etc.) would you recommend to young professionals?

Early in your career, you should try to consume as much information as possible, not just within your industry or discipline either. When you’re intellectually curious, you start to learn that certain things in life touch on many other things. If nothing else, it gives you the ability to be an intelligent person in conversation with others, and everyone appreciates someone who is smart and has interesting opinions.

As you become more senior, the plethora of domain-specific information available skews more to the day-to-day tactical areas versus strategic, and you find yourself in a gap. For those folks, I recommend building your own personal board of directors. Non-profits do an excellent job of this; they might have 35-person board where each board member has a vested interest in the success of the non-profit. I’d encourage everyone to mimic that ‘board of directors’ mentality for your own life. When I come across more complex challenges, I tend to go to someone on my board of directors because I find that their advice and perspective is significantly more valuable than anything I could consume online.

What is the best way for people to connect with you?

LinkedIn is the best way to connect with me. If you’re going to reach out to me, or anyone for that matter (and expect a response), do a little homework first.

For example, you might see that the person you want to reach out to recently wrote an article on self-driving cars. Maybe you just came across a similar article – you could demonstrate you were paying attention to something they clearly care about by sharing the article you found. The tactic of providing a little value is especially important if you’re going to ask for something.

When Jocko Willink addresses a group of sales people he’ll ask them, “Are you sales professionals?” When they say yes, he’ll say “Great, did you warm up today? Did you go around the office and do a quick role-play with your peers? Did you practice? Perhaps discuss a recent objection with your boss, and figure out how to address it?” When the answers come back “no,” he’ll ask the group if they think a professional basketball player like Steph Curry shows up to a game without practicing and warming up? Obviously not.

Bottom line is, if you’re going to be a professional, then you need to put in the work.

If you enjoyed Connor’s career journey, please navigate here to read other stories of impressive leaders within our network.