Craig Stoss

Craig Stoss

This week, I’m delighted to talk to the crackingly capable Craig Stoss!

Craig is based in Waterloo, Ontario, Canada, and is Director of Support at Arctic Wolf Networks, a SOC (Security Operations Centre) -as-a-Service organisation that provides “24×7 Concierge Security” which work around the clock to monitor, detect, and respond to cyberattacks before they have the chance to impact your business. Craig has been with Arctic Wolf for about 8 months, and in leadership for 7 years.

Hey, Craig! Thanks so much for spending time with me today! We’ve known each other a little while now, and though we’ve often talked “support”, I’m looking forward to getting to know a little more about your career and approach to the job today! Can we start with how you got started?

Of course! I was really lucky as a kid, my classroom had a Commodore64 in it. Classrooms having computers were rare in the early ’90s. I really enjoyed programming on it and it set me up with an affinity for technology.

A few years later, the Canadian government started a program to bring this new thing called the “Internet” to rural communities and promote government services online. I was selected as the summer student who was in charge of teaching my community about what the Internet could do. It started with teaching Senior Citizens how to get pension forms online, but in hindsight, what it really taught me was how to combine being social (customer-facing) with using technology.

That only grew at my first university internship as a support rep for a small startup tech company. And I never really looked back. I loved that I could be deeply technical and learn new tech concepts, languages and applications for tech tools while still being social and meeting new people.

I turned that experience into a full-time job after I graduated and have been customer-facing roles ever since.

 I loved that I could be deeply technical… while still being social and meeting new people.

That’s really interesting. I started out teaching other kids at school, and realised I could make a job out of it, too! The kid-teacher to adult-support-professional seems to be a common journey! 

How about moving into leadership? When did that happen?

I have lead support teams for 7 years now. I was working as a technical account manager for a company which was acquired. Post-acquisition, my role had been redefined to be less technical and more sales-focused, something for which I am not suited. Coincidentally, a leadership role for a backline support team was posted at the same time. I had a wealth of product knowledge, knew support, and understood our customers very well. I used that experience to interview and was promoted internally to lead the global team.

Again, it’s such a common story. How did you get on making that transition from individual contributor to leader?

One real advantage was that most of the team I had worked with in my previous roles within the company. So it was a friendly team to come to, they knew me and my style and also, for the most part, knew the goals I was hired to implement. For a first time leader, this removed a huge burden of getting to know the team, which allowed me to focus on making meaningful changes more quickly.

So this was a relatively easy move, then? What changes did you prioritise in those early days? 

The first team I lead was a highly senior, very experienced team. For that reason, they struggled with fewer unique challenges and motivation had been dropping. I was tasked with trying to find ways to increase the morale, while still achieving the excellence in support service that was expected.

I was tasked with trying to find ways to increase the morale, while still achieving the excellence in support service

I brainstormed with the team, that given any budget, any amount of time and any number of resources, what would they like to do that would be engaging, and solve observed business issues. We came up with a list of 4 things. I dedicated time for each person on the team to work on these “extracurricular” activities. They were geared towards the individual’s interests, helped the business, and took away from the monotony of “ticket-in-ticket-out” support they were disengaging with.

The plan succeeded! We made meaningful changes to processes such as support training, knowledge sharing, and technical upskilling. and one of those projects was actually released as a support-related product offering by the company! One of the members of that team is still with the company and leads the team which produces the support assistance tool that came out of those projects.

That’s so great. I love to hear of individual successes like that. How do you nurture that development? 

To nurture development, you need to help each team member explore areas of interest, while still benefiting the overall support department goals. For example, one team member might be more tech writing focused and therefore contribute more to the knowledge base, while another might be more focused on the technology and want to write helpful scripts for the team.

To nurture development, you need to help each team member explore areas of interest

And what about yourself, as a leader? How do you foster your own development?

I use Twitter, Blogs, LinkedIn and Slack communities to network and learn from others. Very few problems within support and leadership are unique. Asking for advice and being inquisitive are the best ways to gain perspectives and learn what you may want to try.

That’s so true. Community and connection are as important to our development as experience and research. Have you had any particularly hard lessons on your journey so far?

The hardest thing I’ve ever had to do is have difficult conversations with someone who I know is a high performer on the team, but just isn’t reaching that potential. It is so hard to motivate someone. I believe that spending the time to show you care and want to help that person grow in their role, learn new skills, and take on bigger responsibilities can have an incredibly positive effect on their career and the value they provide to your company.

The hardest thing I’ve ever had to do is have difficult conversations with someone who I know is a high performer on the team, but just isn’t reaching that potential.

Do you think CS leaders need a particular skill set?

CS leaders really need to be customer-centric. You need to be able to provide the tools, and the freedom to use those tools to your team and allow them to make the right decisions, at the right time to suit the customer needs. Too much process, not enough guidance, or too many restrictions and policies are detrimental to the customer experience. 

Leaders have to make sure the tone of the team is consistent and provides the level of support experience the company wants, and then trust the team to do so.

What will CS look like in the future, do you think? Will that customer-centricity still be key?

With SaaS, apps, and IoT product models specifically, the companies that utilize the data they have to provide customized, low-effort, customer-centric support will be the leaders in the space. Data analytics can tell you when customers are likely to hit errors, or automatically notify support agents something went wrong to allow them to proactively fix it, or when to pop up helpful guides. Guide your customers to success. You provide a product or service, the support burden of which needs to be on you, not on your customers.

Guide your customers to success.

My perennial favourite question for last – what’s your favourite way of signing off? 


Cheers, Craig! What’s the best way for folks to contact you, if they’d like to get in touch?

You can reach me at, or on Linkedin at I’m on Twitter, too, at @StossInSupport!

Great! Many thanks for your time, again. I look forward to seeing how your predictions there pan out! 

Watch this space for more CS Leader interviews in the very near future!