Wingman Direct Marketing Celebrates 5 Years

Wingman Direct Marketing

Wingman Crew member Mark DeWit here. I’m a Digital Marketing Intern here at Wingman Direct Marketing. I sat down with Crew Chief David Daigle to celebrate and reflect on Wingman’s five year anniversary. David has had a huge impact on everyone who has come across Wingman. Myself and many others are very thankful for all he has done. 

Here are some words of advice that have helped Wingman Direct Marketing get to where we are today: 

1. Focus on solutions, not services 

2. Focus on each next step at a time 

3. Stay lean and reinvest in your business 

4. Use your time wisely – sometimes it makes more sense to outsource that to do everything yourself. Remember how much your time costs. 

5. Love what you do – your passion will carry you a long way! 

Here’s 7 questions answered by David Daigle:

1. Tell us the story of why you started Wingman Direct Marketing

As we’re celebrating our fifth anniversary this month, it marks five years ago since I got the news that I was going to be reorganized out of my second blue-chip company position in a matter of about 16 months. It was then when I decided; you know what, it’s time that instead of working client side, I start working for myself to take control of my future.  

So Wingman started as Daigle Direct and then morphed into Wingman Direct Marketing a couple of years later. It absolutely was the right timing and opportunity, and looking back five years, it was the right thing to do.

2. What was one of your proudest moments during these past five years?

[laughs] Making it to five years? I don’t know if you know the statistics Mark, but, something like 49 or 50% of companies fail before they get to the fifth year. But if I were to narrow it down to a single moment, it’s been to get the opportunity to understand what small businesses are all about. The project Gazelle is probably one of my favourite clients. Being able to help so many women entrepreneurs in rural Alberta and Saskatchewan has probably been my proudest moment wearing the Wingman jacket.

3. What Is the most common problem Wingman has Solved for its Clients these Past Years

We pride ourselves on being a strategy first company. People have knocked on our door and asked for help with whatever tactical things they need help with whether it be a website, social media, or direct mail. I think what we do the best is we help them truly understand who they are and what they really want/need.  

We do that by getting a good understanding of where they are, where they hope to go, what their objectives are, and their pain points. We really aim to understand the personas they’re targeting and their unique selling proposition whenever possible. If we don’t understand in a nutshell who they are, what problem they solve, and who they solve it for, every bit of marketing is a waste of energy and effort.  

So that’s been the biggest thing that although people come with an ask, we solve what they actually need, not necessarily what they initially thought they wanted.

4. What’s been the most surprising about the journey so far

I don’t know if I should have been surprised, but how hard it’s been [laughs]. The entrepreneurial spirit is an interesting thing. You need to be able to be a jack of all trades and a master of as many as possible. 

It’s been hard but it’s also been absolutely worth it. It’s been great working with all the different clients we’ve had and all the crew members we’ve had in the Wingman crew. The solutions we’ve came up with and the sheer volume of content we have created for websites, social posts, and blogs has also been surprising in the best way. There are just so many moving pieces, and with the pandemic in the midst of these past five years of Wingman’s tenure, it’s been surprising how hard it’s been.  

However, it shouldn’t be surprising because every entrepreneur goes through this.

5. If you could go back five years, what’s one piece of advice you would give yourself 

I heard a term in the last three to six months that I absolutely love and it’s called: ‘TNT.’ It’s not dynamite. It’s actually ‘today not tomorrow.’ What that means is if you have even an ounce of a procrastination tendency, you need to break it. You need to.

The idea that you still have time to do X, Y or Z is a dangerous thought. You may have time to do it, but X, Y, Z then gets added onto A, B and C and then J, K and L. So if you are procrastinating by deferring to tomorrow what you could have done today, tomorrow is that much busier. And then the next tomorrow is that much busier. So again, I love that term TNT meaning today not tomorrow. I wish I kicked myself in the butt five years ago with that expression.

6. Where do you hope Wingman will be in the next five years?

That’s such a great question without a great answer. Sadly, five years ago, I didn’t know I would be here today. I did a proper business plan five years ago and revisited it about three years ago. And I definitely need to revisit it again in the next handful of months to plan for the next three to five years. 

I definitely know I have a better understanding of what Wingman is right now than I did five years ago. I now have a good understanding of what clients we work best with and what solutions we solve for. So with that said, what I hope is to be an entity that has the appropriate amount of clients and staff to be comfortable and know the today and tomorrow.  

Although it’ll be hard, it’ll be worthwhile. It’ll impact our clients, Wingman employees, and families. So it’s kind of that triple win that’s best for all of the above. I want to be in a place where I’m in a triple win situation.

7. Being named Wingman Direct Marketing, what is your favourite airplane?  

When I was about 12 or 13, maybe 14, I was in air cadets. We had a camp in the middle of summer where we went up to Cold Lake Alberta to the air force base. A couple of us broke through the barracks. We were peeking through the fence at all of the awesome F-18s, and then we went up on the tarmac.  

One of the pilots saw us all looking through the fence, so he came over to us. Then one by one, he allowed us each to sit in the cockpit of an F-18 which was absolutely mind boggling. So the F-18 is by far my favourite, just because I’ve literally had my hands on the controller. I’ve playfully clicked a couple of buttons, and what have you. I’ve clearly never had the opportunity to go up in an F-18. Still, I’ve had the opportunity to go up in several different midsize airplanes over my career in air cadets. 

The aviation theme has run thick through my blood ever since I was a tiny, small kid.


The Wingman crew can’t thank you enough for the past five years. Like anyone’s past five years, a lot has happened. As we look to the next five, we are excited to take on any challenge that comes our way. 

You don’t have to fly solo! Book a Wingman today to get started.