We Did It

It happened. We actually pulled it off. After 9 months of planning, we gave birth to the first cyber security-focused conference in the Waterloo region. It was a hell of a lot of work, with a fair share of hurdles, speed bumps, and every type of hazard you can imagine mixed in, but we did it. Myself and 4 other organizers have put together an amazing conference that went smoothly; far better than any of us could have imagined. This post is all about the journey, the “behind the scenes” look at how this came together and hwo I personally got involved in all of this. It’s a thank you letter to our organizers, speakers, vendors, sponsors, and of course, our audience. Thank you, all of you, for helping make this a reality.

In the beginning…

I’ll be honest, this idea was born out of a few beers between the first organizers, Jamie Hari and Lewis Humphreys. Jamie took the bull by the horns and took care of the major lifts - incorporating, setting up the banking details, writing up sponsorship packages, and all of that. But that comes a bit later in the story. Jamie roped in Dinah Davis next, who runs the local KW Cyber Security Meetup. Jamie and I have both spoken at the meetup in the past, so we knew of each other. It also made sense to reach out to Dinah as she had a pulse on the local security scene through the meetup. All of this transpired in early February, just before I became involved.

There was another fairly large conference coming up, True North, that was happening in June. Lewis managed to get a workshop spot, and figured this would be a great way to announce the new conference, Cyber City, to the area. The topic for the workshop? A tabletop exercise of course! At the mention of tabletop, Dinah immediately though of me. The rest, as they say, is history.

This wasn’t my idea

I’ll be honest, I wanted to start a BSides Waterloo myself, but I was going to wait a year or two before trying to spin one up. I’ve got a lot on my plate as some of you may know, so I wanted to be patient and get my research done first. However, when opportunity knocks, you just have to answer the door! I jumped at the opportunity to help Jamie, Dinah, and Lewis to get this conference off the ground. I’m all about the community, and I’m very keen on giving back. After all, I pivoted into security half-way through my career, so I definitely have a lot of desire to give back for all I was given. This seemed like a great way to do it.

So many meetings

We decided on meeting every week to discuss the conference details. We did everything, from planning sponsorship packages to deciding who would run the social media campaigns. Stickers, post cards, and other marketing materials were designed, printed, and shared out in the community. We talked about the venue, the swag, lunch, drinks, and of course rentals for everything needed for that day. We also discovered in the final few weeks that we needed proper audio equipment since the assumption that what was at the venue was sufficient. It wasn’t, but thankfully we had an awesome vendor who came through with an awesome audio technician to help us for the day. Many thanks to Sherwood Audio for the save here!

Know when you need help

Early on when we were planning on lunch, we realized we were out of our league. Pam Cruz works with me at my current job and is our Office Manager. Pam is a machine, and is responsible for weekly lunches that feed 150+ people. I knew of nobody better who could help us with lunch, but as she so often does, she surprised us even more with her vast number of contacts with various swag vendors, printing vendors, and other companies that helped us with the finer points of the conference. Pam certainly is a major cog in the machine that is Cyber City.

Planning is nothing without testing

We discussed scenarios for the True North workshop, and we even did a dry run at the meetup to see how it would go. I’ll say it - it was a complete failure. This was a new style of tabletop I hadn’t done before, and logistically it wasn’t idea. Having said all that, it was the exact learning experience we were looking for, so when True North came around we knocked it out of the park.

One of the things we learned from the test run was that having certain “twists” didn’t work out so well, and that not everyone is cut out for leadership. Also having some strong voices in a team can drown out and potentially de-rail your simulation, which is why we had a dedicated “host” being our leader for the True North event. What do I mean? Well during the meetup one of the twists was that the company was in the middle of an acquisition, and only the CEO and Legal team knew about it (we didn’t have a finance team), so there was a lot of back-and-forth going on about exposure and whatnot, all while leaving the other teams out of the loop. We actually put the teams in different rooms, but that ended up being more of a hinderance than anything. Oh well, it was an eye opener for me at least!

Plan, but plan carefully

We would track items in our meetings the old fashioned way - with notes and our own memories. Sometimes we would get fancy and use Slack to co-ordinate efforts, but it ultimately meant we were forgetting things. We’re a non-profit, so purchasing something like Jira was out of the question (not to mention overkill), so we went to Trello. I opted to setup the board in a Kanban style, which worked out quite well. We did some modifications to it initially, but came back with a Kanban style with labels, due dates, and assigned cards. That became our proper plan, and I attribute this use to a huge part of our success. Lots of lofty goals and ideas were added, but they were delegated to the backlog. We sorted by due date and held people to those dates. Some things slipped and went past the point of no return, but thankfully nothing bad happened. The lead time on swag is long, and if you aren’t careful then you don’t have time to make changes.

Learn from others

Each of us has either attended or been a part of conferences. We all had ideas on what was good, what wasn’t so good, and what we just wanted to outright avoid for our own conference. Based on this, we started planning the details. It was very easy to get lost in the weeds though, which is why having a strong plan is important! Even more important is having a military-like lead who holds people to the schedule and keeps us on track. I played that role for the most part, but it wasn’t that bad as my fellow organizers kept us all on target when we started to drift.

It’s Go Time

A few days before the actual conference, I was in a state of eerie calm. The week before I was an absolute mess, and I did have my nerves kick in a bit the day of, but overall I was fine with it. We had planned everything to the best of our abilities, so now it was all about execution. Jamie was a bit nervous as well, but I told him the same thing I had told myself: All the planning is done and the time for panic is over. Everything is in place now, so either it’s going to work or it’s not. There’s nothing else for us to do.

Of course there was still a ton of things to do! We had to adjust a few tables, set out tablecloths, co-ordinate sponsors and speakers, handle check-ins and hand out badges, as well as co-ordinate coffee, lunch, and drinks for after the conference. Jamie and Dinah did amazing with their shared MC duties. Pam did what she did best and focused on execution. Lewis was our spiritual guide in all of this as he had to man his own sponsorship booth for University of Waterloo. I did what I could with the speakers and the check-in desk when new badges needed to be printed, but I mainly kept to the shadows.

Final Verdict

We had 200 people registered for the event, with another 30+ people on a waiting list. We had 8 amazing speakers come and present, and an incredible lunch. We share the general opinion that the lunch packaging was a bit on the wasteful side, and the fact that our venue did not have recycling bins are all facts that we’re taking back with us as we plan for next year. 200 attendees, 8 speakers, 1 amazing day. Those numbers are hard to beat. But most importantly for me at least is that we brought our community together. We opened the door to showcase how strong of a security culture we have here in Waterloo region and I couldn’t be happier.

I can’t wait to see how things turn out next year now that people know what to expect. To them I say the same thing we said to all of this years attendees:

Welcome to the Cyber City