Q & A: InsightSquared Sales VP: Steve McKenzie

Our goal at Building the Sales Machine (BTM) is to enable sales leaders in the tech community to help and learn from each other. We’re all in this boat together, trying to help revolutionary companies disrupt the norm and make people’s lives easier, better, more fulfilling. We’ll aim to bring some of these great teams, leaders, and strategies to life through our articles, meet-ups, speaking events and interviews.

In today’s post, we spoke with Steve Mckenzie, Sales VP at InsightSquared.  Before joining InsightSquared, Steve spent six and a half years at enterprise cloud provider Mimecast where he wore many hats including head of European Sales, Head North American; marketing, strategic alliances and enterprise sales.  We’re particularly excited to be doing a Q&A with someone from InsightSquared, because we’re big fans of the quality content they put out on their blog!

Steve’s thoughts below:


BTM: What’s something you’ve learned from a sales person in the last 3 months?

Steve: I’ve learned a lot from coaching our newest sales reps. Sometimes, I take for granted some of the embedded knowledge I have gained as an experienced salesperson. For example, one of the key things for a salesperson to do is to mutually agree upon timeline and next steps with a prospect. It seems straightforward enough, but it is something many inexperienced reps struggle with. A lot of it comes down to confidence. Confidence often comes with knowledge, so we have to empower our sales rep with greater knowledge.

Coaching our new sales reps reminds me that experience does count — you can’t take it for granted as a sales leader. You have to remember that you’ve gained your knowledge and skills over years. It’s difficult for new reps to pick some of the more nuanced sales skills in one training session. You have to stick with coaching them, keep reinforcing your ideas, and offer continuous support and training. Using real life stories helps contextualize a specific strategy.


Most interesting thing you’ve learned about your sales team from looking at the numbers?

Steve: We constantly analyze our sales process from the very top of the funnel all the way down to closed-won and closed-lost deals. It may seem obvious, but when doing this, you realize that pipeline production is absolutely integral to your success. Many sales leaders focus on the bottom of the funnel and closing activities, but you have to pay close attention to what’s happening at the top, because that’s a leading indicator to future success or failure. (To monitor this, I can instantly pull up a screen in InsightSquared and immediately recognize if/when we don’t have enough pipeline). It’s crucial to have one eye on the top and the eye other on the bottom of your funnel, and it’s not just about quantity, either. You also have to be able to measure quality. Deep pipeline inspection is fundamental to success. These metrics don’t lie.


Best tip for sales teams that are scaling rapidly?

Steve: Invest the time and money in a solid onboarding program, and make early-stage training a top priority. Often, a lot of onboarding responsibility falls on sales directors, but the problem is, they have a day job and numbers to hit, too.  By allocating dedicated staff and resources to ensure quality onboarding and training, your ramp periods will be shorter, you’ll have less team attrition and your team will be happier and more motivated.


What traits do you look for in a sales person?

Steve: Attitude, aptitude, and culture fit. I look for people with can-do attitudes, problem-solving skills, and those who are self-motivated, ambitious and competitive. I think of aptitude as a form of IQ. I look for people who are smart enough to figure things out on their own and problem solve with less-than-perfect information. Great salespeople are inquisitive. They ask questions of other people and have a thirst for knowledge, but don’t rely on others for their success. Regarding finding a good culture fit, I seek out people who are going to contribute to the overall culture in the organization and be a solid team member. It’s a gut feel, most of the time. I’ll just ask myself, ‘Would I want to sit next to this person?’ Culture fit can be hard to pinpoint, so that’s why we also conduct several interviews with many different people in our company. This approach helps ensure diversity on your team, and that you’re not hiring a bunch of people who think just like you.


What role do sales operations and sales enablement play in your organization?

Steve: Sales operations ensures that your company’s sales machinery is oiled and up and running optimally. At InsightSquared, this involves doing deep business analysis, rather than just surface level analysis. Sales enablement involves evaluating the tools and technologies that can help sales teams be more efficient. We’ve found that by providing clarification and differentiation between these two roles, our sales team runs much more smoothly.


SteveSteve McKenzie is the VP of Sales at InsightSquared. Before joining InsightSquared, Steve spent six and a half years at enterprise cloud provider Mimecast where he wore many hats including head of European Sales, Head North American; marketing, strategic alliances and enterprise sales. Prior to Mimecast, Steve ran a media business in South Africa and in the early part of his career had roles in finance and sales. Steve has an MBA from the University of Cape Town and when he is not buried in his work, like to keep fit and balance his other job as husband and father to three young boys.