Studies In Selling: One On One With Darren Roos

I spoke to Darren Roos, the CEO of IFS, about his best sales advice

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Adam: Thanks again for taking the time to share your best sales advice. First things first, though, I am sure readers would love to learn more about you. How did you get here?

Darren: My journey has been slow but iterative. Very early on in my career, I worked for a company where we sold a travel benefits package in a multilevel marketing environment. That was where I really learned to sell. In a short space of time, I needed to get someone excited and passionate about the product and understand the rewards they could reap. That learning was critical because it formed a strong foundation from which I advanced in sales and progressively took on more complex roles. I went from sales manager to sales director to country manager to regional leader to regional president to ultimately running multiple regions and finally, running a global business. But irrespective of whether you’re a junior person in an organization or the CEO, you’re selling all the time, whether that’s to investors or to customers.

Adam: What is the single biggest sales mistake you have ever made and what did you learn from it?

Darren: In a past role, we were trying to close a large transaction that would be transformational for the business I was running, and for the whole company. Because we were a publicly-listed company, it was time sensitive and we needed to get it closed in a specific quarter. We put a tremendous amount of pressure on the sales team and customer to get the deal done and we succeeded. But in the months that followed, there was a bad taste in the mouth of the customer. It took a very long time for the relationship to recover.

What I’ve learned from that is that you’ll always have quarterly pressure. It’s a reality of any business. But you must make sure you’re not forced into a position to eke out that last deal. You must have a forward-looking pipeline. You must be well prepared and that your timing is clear to the customer, as well as theirs to you as the vendor. You don’t want to end up in a situation where you apply pressure, due to confusion on timelines, that can ultimately do more harm than good.  

Adam: In your experience, what are the key pitfalls to succeeding in sales and how can you overcome them?

Darren: There’s no shortcut; nobody buys unless they understand why they’re buying and why they should buy now. That’s just a simple fact. Lots of sales people fail to address that. They hope the customer will get through their buying cycle. And some customers do but then you’re flipping the coin on whether they’ll buy from you or someone else. So, the biggest pitfall is not understanding the underlying fundamentals of creating demand and a sense of urgency.  

Adam: What are your three best tips when it comes to selling?


  • Never stop prospecting. Invest time in building your pipeline so you can be selective about the kinds of deals that you do and customers that you do business with.
  • Make sure you are always building value. This is particularly relevant in the software environment, but also other sales environments. The customer needs to understand what it is they are going to derive from a purchase. So, change it from being a commodity to something that delivers real value. In the software world, we can go in and sell a certain number of users and specific discounts based on user counts, or we can really articulate the value of the solution and take a share of that value. The value sale is more significant than a commodity sale. Your competitor is likely to be selling their product in a less sophisticated manner. This strategy will give you a competitive advantage.
  • Make sure you have a robust plan. Ensure you have a plan for each deal that clearly defines the milestones that you need to close. And make sure this plan is agreed by the customer. They don’t necessarily need to agree to buy it from you, but they do need to agree that the timeline you’ve laid out works for both of you.

Adam: Describe your sales methodology. Have you found that different types of prospects are responsive to different to types of styles, and if so, do you adapt your style to the type customer you are selling to?

Darren: There isn’t a right or wrong sales methodology but there are a few elements that need to be present:

  • Be adaptive to the type of customer you’re dealing with; personality is a big thing. You can’t underestimate the value of chemistry between a buyer and seller. People do business with people. People want to do business with people they like, and people don’t want to do business with people they don’t like.
  • Get the basics right. The requirements are defined, and the customers’ needs are clear. Make sure you understand the value the customer wants to derive and articulate why they should buy it from you versus somebody else.
  • Connect with all the decision makers involved in the purchase, and ensure they are on board with your solution. Those fundamentals are key, regardless of what you’re selling.  

Adam: What sets your approach apart from others in your industry? Describe your industry and your best tips specific to selling within it.

Darren: In the enterprise software industry, deal size can be very large and the competition is dense. The approach I advocate is one in which you are always conscientious of responding to your customer’s needs. Early on in my career, I won a very competitive bid at a large financial services organization. When we won the deal, we asked ‘why did we win?’ The decision maker said it was because we listened. The others came in with a standard approach to the problem rather than a recognition of the problem as the customer saw it. This is particularly relevant in large complex deals, especially in the enterprise software industry.  

Adam: What do you believe is the hardest step in the sales process and how can it best be navigated?

Darren: Particularly in the software industry, customers follow a formal process because of the size and complexity of the deals. Getting short-listed is typically not difficult given there are only a small number of vendors that can address clients’ specific needs in our industry. The most difficult step is moving from being short-listed to being the final choice. So, you must represent a differentiated proposition. And that differentiation in our industry often relates to mitigating risk, even if it’s perceived risk.

Getting the final decision is generally contingent on the following:

  • You’ve been able to clearly articulate the customer’s problems
  • You have convinced them that they will realise those benefits if they select you

Adam: What are your best tips for improving your close rate?

Darren: Converting from pipeline to close is the most important thing you do so, make sure you’re only chasing deals that you can potentially win. Make sure your solution is a good fit for the customer before you decide to enter the chase. That way you know you’re investing your limited time and resources only into deals where you have a good possibility of winning. Your close rate will spiral out of control if you chase business that you can’t win.

Adam: What is your best advice around making the ask?

Darren: Be bold. When you can, clearly articulate your value to the customer. For example: if you’ve done due diligence and you can deliver $20m in annual savings, then you can say the customer has signed off on the potential realization of $20m in annual benefits. To deliver that benefits realization, that will cost the customer $5m a year. So, they will potentially see a net savings of $15m a year.

That’s a far more strategic approach than to say, ‘here are the software modules you’re buying. And here’s X amount per use and here’s the professional services cost to realize your project.’ I would guess 95 percent of our competitors are still presenting cost for software and cost for services versus a cost to realize a set of benefits. And a set of benefits that a customer has signed off on. When you frame things in this way, it translates directly into the benefit the customers want to derive from the project.  

Adam: Language is obviously very important throughout the sales process. What are key phrases or words you have found have helped or hurt your chances of success?

Darren: You have to engage on your customer’s wavelength. You need to speak the language of the customers you’re selling to. So, if it’s a factory manager then you had better be at their level. If you’re selling to a CEO, you had better be at their level.

Adam: On a scale of 1-10, how important are ethics to succeeding in sales? Explain.

Darren: Ethics are 10 out of 10 importance for long-term relationships. In enterprise software sales, we tend to have multigenerational relationships with customers. You can’t afford to get it wrong. Behaving in a way that fosters a relationship that is mutually beneficial one of the most important things you can do.

Adam: What is your best advice on how to best manage and stay on top of leads?

Darren: Use a good CRM system and be religious about its use. You can’t manage a business without a strong adherence to good CRM hygiene.

Adam: What is the single best piece of sales advice you have ever received?

Darren: Managing up is as important as managing down. What I mean is that success is a function of expectation and performance. If your performance is outstanding, but the expectation is higher, people will perceive that you have failed. You must take ownership in managing that expectation so that when you deliver outstanding performance it is recognized as such.

Adam: What sale are you proudest of? Walk through how you made it happen and its significance.

Darren: I’ve done hundreds if not thousands of deals over the years. From $50k to $50m. I think back to a deal I did early on in my career. When I was selling Siebel Services, the customer awarded us the business, maybe only a $30K or $40K deal at the time. There were 6 or 7 vendors around the table who had the exact same briefing. We all had capability to fulfil the customer’s requirements. I won the deal because I picked up on nuances in the customer’s requirement. To this day, I stay in touch with that manager and we have done more business. So that early deal in enterprise software services has a soft spot in my heart.

Adam: What is one thing everyone can do tomorrow to become better at selling?

Darren: Listen more than you talk. When you’re with a customer you learn nothing when you’re talking. To be successful, you must understand the customer requirements. Get them talking. You have two ears and one mouth, use them in that proportion.

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