SalesTech Star

SalesTechStar Interview With Dave Gillmore Head of Sales and Business Development at CyberCube

Dave Gillmore, Head of Sales and Business Development at CyberCube joins us in this SalesTechStar interview to talk about his journey into the cyber insurance industry while also sharing key tips for technology sales to better utilize their CRMs which he opines, “Are very under-utilized.”

Read on to catch his tips and insights on technology sales:



Can you tell us a little about yourself Dave and a little about your professional journey so far. What have some of your biggest B2B Sales learnings been so far?  

For the past 15 years, I have been in software sales and business development, spending most of that time working in cyber security solutions, selling into mostly large financial institutions and communications companies.  In 2016, Symantec began building out a cyber insurance business group. As I started to research the cyber insurance industry I saw a huge opportunity. The cyber insurance industry is growing exponentially and with the ever expanding use of the digital assets and the internet to run our businesses and lives, the need for cyber insurance will only continue to grow. And when you are in sales, you want to be in a growing industry with growing needs and a product that can serve those needs. That is what CyberCube is positioned to do.

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In your past experiences in Business Development / Sales (at Symantec, etc), what were some of your biggest challenges in your roles/what strategies did you use to overcome them? We’d especially love to know about some of your most successful sales campaigns from your journey so far!


 One of the biggest challenges we faced was when the decision was made to spin our Symantec business unit off and form our own independent company (CyberCube).  While the move was exciting and held a lot of potential, the challenge was that we had built a pipeline of potential clients for the products that we were about to launch as Symantec. With us spinning off, would that pipeline erode without the big brand of Symantec behind it and with the new uncertainty of an unknown brand (CyberCube) and a small team? However, we were able to keep key personnel from Symantec and stay in constant communication with our prospects to provide the assurances needed that the move would be beneficial to the product and its future. Because of that transparency, strong confident messaging and steady engagement with our prospects during that transition we were able to hold on to most of our pipeline and landed two of our largest target clients within the first two months of operation as a new company.

When it comes to the common industry challenges in B2B Sales/Tech Sales today (personalization at scale, cold calling challenges, launching a successful go-to-market strategy etc) – what are some of the most common challenges you see teams face today and how would you advise they solve them?

Most of my career has been selling very complex technology to sophisticated buyers. Often, sales cycles are long and very consultative. Because of this, one of the keys to success is to really hone in on your prospect’s needs and challenges. What will make them successful to their bosses and shareholders? Show them how your solutions can help drive some of that success. You can also take the learnings you have around your clients’ uses cases and needs to help form or modify your GTM strategy.  It is important to learn from your clients and prospects to adjust and improve your messaging, targets and approach.

What are the top 5 Channel Management/Partner Management/ Alliances Management tips and strategies that have worked for you in B2B?

  1. Business is personal. In complex sales, relationships are critical. You need to build trust and confidence with your prospects. Additionally, people buy from people they like. So spend time to get to know your prospects on a personal level and you’ll see greater success.
  2. Don’t win and lose deals alone. For most of my sales, a team of technical experts and subject matter experts are required to win business. A good sales professional is able to identify client needs and get the right internal resources/experts in the room to address those needs.
  3. Be transparent and honest. Don’t play games and mislead your prospects. Where your solutions have gaps, don’t shy away from them. Paint the right picture around what your solutions and teams can and cannot do and it will set you up for longer term success and trust.
  4. Always have an objective or outcome with every interaction you have with a prospect/client.  Maybe that is to secure the next meeting, maybe it is to find out about a particular need, maybe it is to educate them on something in particular. Too many times, I see sales and BD reps go into interactions without clear objectives and often that leads to a lot of talk but very little progress towards a purchase or more business.
  5. Try as we may to understand our prospect and client needs/priorities, it can be hard to always know and understand what will resonate. Thus, I’ve adopted a philosophy that when selling and/or communicating with any prospect there is likely only a 50/50 chance that what I communicate will resonate with them or land providing the benefit intended. However, when the prospect is talking 100% of what is being said is important. Thus, I try to be mindful to ask questions, listen and not dominate the discussion with my point of view and pitch. Instead, by getting them to talk more they reveal the path to success for you and then you only need to align your selling points to their expressed needs. I have found really successful sales professionals spend more time listening and asking good questions and less time pitching.

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What SalesTech tools do you wish more Tech Sales/B2B Sales teams would use more of, which SalesTech products or categories of tools do you think will show falling demand over time?

Easy to use CRM systems are underutilized in my opinion. Too often I see sales professionals allow their email inboxes to dictate their daily focus and work. If you can get out of your inbox and really use a quality CRM system to manage your daily tasks and interactions I think reps would see greater success. We all have CRM solutions but most salespeople I know just see them as reporting tools and not truly a way to manage their business.

I think the use of email for prospecting new business is also becoming less and less useful. Our inboxes are so full that less and less people are responding to email, so finding new ways to engage your clients is critical (think about utilising social media, conferences, industry events, etc…)

How do you eventually see salestech play a role in the future role of the typical B2B/sales professional? 

Data is key. Today there are so many sources of data and benefits. The key is to not be overwhelmed and to find the right sources for your industry and use that to focus your efforts to improve your efficacy.

What according to you are 5 must-haves (personality/work traits) every client-facing executive or Sales team member should have?

  1. Welcoming personality – The beer test. If the person is not someone I would want to sit down and have a 30 minute conversation over coffee or beer with, then they are unlikely to be very successful in building client relationships.
  2. Good listener and asks good probing questions – When I interview new sales reps, I care less about what they say to me and more around what questions they are asking and if they can take my responses and tie my needs and challenges into their self-pitch.
  3. Need to be able to tell a story – people don’t like to be sold to.  But they like a good story.
  4. Collaborative – reps that can guide and work with a team of people often are much more successful than the lone wolf.
  5. Persistence – find a way to continue to add value to your prospects by being a source of thought leadership or expertise, even when they are not buying right now.  That persistence will lead to results.

Tag (mention/write about) the one person in the industry whose answers to these questions you would love to read! 

Mike Campbell – Chief Sales Officer at Equinix. He’s one of the strongest sales professionals and leaders I’ve ever known. He builds incredible teams and manages clients and executives masterfully.

Your favorite Sales/SalesTech  quote 

I have lots but one I have used recently is “The way to get started is to quit talking and begin doing” – Walt Disney

Tell us about some of the top sales/salestech/other events that you’ll be participating in (as a speaker or guest!) in 2020!

In the coming months I will be at RSA, Insurtech Insights London, and 2020 Advisen Cyber Risk Insights Conference

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CyberCube logo

CyberCube delivers data-driven cyber analytics built specifically for the insurance industry. CyberCube is focused on solving the most difficult and important cyber risk challenges in insurance with world-class analytics.

Experienced Sales and Business Development leader with a demonstrated history of success working in cybersecurity software and insurance analytics technology. Skilled in Team Management, Negotiation, Sales, Enterprise Software, Cyber Security, and Go-to-market Strategy. Strong sales leader with a Juris Doctorate from Seton Hall University School of Law.