Selling into Ever-Changing, Highly Regulated Industries – Part 1: Technology & Cyber

Mar 25, 2021
Author: collin stewart

This is the first blog in the Selling into Ever-Changing, Highly Regulated Industries, featuring tips, tricks, and tactics from sales professionals selling into heavily regulated spaces from cybersecurity, to healthcare, to cannabis. Stay tuned for 2 bonus podcast episodes and an ebook on this topic coming soon.

Derek May, a recent guest on the Predictable Revenue podcast, is an insurance expert specializing in technology and cyber. He works with technology companies to keep them compliant with their contracts and works with companies of all kinds to keep them compliant when it comes to data. And while Derek hopes his policies will be nothing more than a safety net for his clients to fall back on, being aware of every risk and every regulation that could impact his clients is vital.


On the tech side, Derek is dealing with mostly Canadian clients signing big contracts with US-based customers. In Derek’s words, the US is a highly litigious environment. This has led to a dramatic increase in contractual requirements for Canadian vendors.

US clients want confirmation that vendors have coverages in place, and they expect higher limits and broader coverage – pushing the envelope of what was traditionally expected of Canadian companies in these international contracts. The risk in breaching a contract, of course, is being sued for financial losses. HUB covers them in this worst-case scenario.

On the cyber side, Derek is helping his clients remain compliant with the various regulations coming out around the world. The EU has GDPR (General Data Protection Regulation), Canada has PIPEDA (Personal Information Protection and Electronic Documents Act), California has CCPA (California Consumer Privacy Act), and the other 49 US states have a patchwork for cyber laws in place. Derek’s customers need to be compliant not only with their local regulations but the regulations in their clients’ jurisdictions. 

The risks as far as data breaches go are epitomized by an article Derek read the day we recorded the podcast. Uber CSO, Joseph Sullivan, was charged with covering up a 2016 data breach that compromised the personal information of 57 million drivers and users. This story is a big deal in Derek’s space. Uber, one of the biggest, most well-known brands in the world, is being penalized because of improper behaviour in covering up a data breach.

This is the first time such a public figure is being scrutinized to this extent for a cyber breach, and it will shift the way people treat these types of losses. They can no longer be swept under the rug, Derek explains. There’s now conviction and a hefty jail sentence waiting for culprits who don’t follow the legal protocol.


To stay up to date on everything going on in the tech and cyber industries, Derek maintains that you have to jump in with both feet. To do so, he attends webinars put on by lawyers, law firms, and different insurance companies, by going to cyber conferences, and by doing a lot of personal due diligence.

Only once you commit to investing your time and energy into becoming an expert in your industry can you become an advisor to your clients.


When Derek comes across something in his research that would be relevant to his clients, it’s his responsibility as their advisor in this space to share it with them. Take COVID, for example. Data breaches have gone up exponentially since March of 2020. There have been more hacking attempts and more, as Derek puts it, “bad actors doing bad things.”

In response, HUB put out a timely content piece to remind their clients to be on high alert. They let them know some of the statistics and what they could do to protect themselves – both providing their clients value and staying top of mind as experts their clients can trust. Creating a relevant piece of content like this allowed Derek to reach out to many clients at once.


Derek has never viewed himself as a salesperson. He’s not with HUB to sell his clients insurance policies, but rather to advocate for them, provide them best practices, prevent breaches from happening in the first place, and act as their outsourced risk manager. Commission salespeople can get a bad rap for being money-hungry and willing to push their clients into anything to hit their quota.

But Derek’s approach is the complete opposite. He tries to build lifelong relationships with his clients so they’ll stay around for 30+ years. The commission he sees from renewals from happy clients is just icing on the cake.

Building that trust starts with how you approach each conversation with your clients. If you’re responding to their industry-specific questions with phrases like “I’ll get back to you,” or “let me find out,” you’re showing them you don’t know your stuff well enough.

In fact, Derek has gained many clients who have left their past broker as a result of that exact scenario. To gain your clients’ initial trust you need to give them direct and immediate feedback and be more knowledgeable in your area than even your client is.

Next, you need to be around whenever they need you. In a fast-paced, digital world, people expect fast responses. If you can’t get back to them faster than your competitor can, you could lose the client.


As one of the most qualified and educated people in this space in Western Canada, if not the whole country, Derek is a go-to resource. But that title was hard-won. It has taken him more than 8 years of work, attending industry events, learning, and pounding the pavement to build his reputation.

But Derek describes working to build a reputation as a flywheel. In the beginning, it’s barely moving, but the more effort you put in, the less effort it requires to spin. Soon, the wheel is spinning faster and faster with no effort required. 

At the start of his career, Derek did a lot of heavy lifting to win his first customers. These days he keeps those customers and gets even more referrals by working hard, always doing what’s right for the customer, never being unethical or overstepping, and having due diligence in place before committing anything to the customer. But Derek never gets complacent – he’s always cognizant that all it takes is one misstep to damage his reputation and the flywheel will come to a grinding halt.


The final piece of the puzzle for Derek is continued personal development. You may be a salesperson, and therefore your expertise may be in sales. But your customers are experts in something else, and to be a truly great salesperson you need to be able to put yourself in their shoes.

Derek believes that salespeople should jump at the chance to learn what their clients care about and to build knowledge in their area. If you do that, when they come to you with a bunch of industry-specific questions and jargon, you won’t skip a beat. And the more you can relate to your clients, the better chance you’ll have at being successful in selling into a highly regulated industry.


It’s difficult to sell into a highly regulated industry. Whether you’re selling into the Petroleum & Coal industry, Pharmaceutical industry, or, like Derek May, the Technology & Cyber industries: regulations are constantly changing, and your customers expect you to adjust and come out ahead of these changes at every turn. But if you don’t have a good strategy for keeping up to date on everything going on in your industry, you’re never going to build the trust you need with your prospects.


More on becoming a trusted advisor to your clients: How to Get The Attention of Any Decision-Maker to Expand Your Sales Within An Enterprise Account

And on building trust:

The Importance of Relevance and Trust in Outbound Sales

How to win your prospects’ trust

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