Season 01 / Episode 027

Diana Gee-Calingo, Sr. Affiliate Manager for Tailored Brands – Men’s Wearhouse and Jos. A. Bank

With Diana Gee-Calingo - Sr. Affiliate Marketing Manager, Tailored Brands

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Are you ready for a very bubbly and educational podcast episode? I hope you are because today we have one of my favorite guests on our podcast, and I think you’ll find her personality as joyful as I do. Diana Gee-Calingo is the current Sr. Affiliate Manager for Tailored Brands. You may have heard of their men’s clothing brands – Men’s Warehouse and Jos A Bank. I have and am also a customer.  In fact, my first suit I ever bought to land my first job in the internet marketing space was a Men’s Warehouse suit!

Diana and I have a lively conversation about everything from cooking and baking (man I can’t wait to get some of her fresh baklava), to working remotely, to affiliate marketing and to working through a bankruptcy in the affiliate channel.

One of the highlights of the podcast is geared toward those who want to move upwards in their career.  Diana lays out her strategy for advancement and it begins and ends with the word “yes”. Saying yes to just about every opportunity allowed her to take on projects, demonstrate success and get that next big gig.

She also dives into what she would want employers, leaders and managers to know about working remotely. Hint – it’s probably not what you think but it is a vital and may make a huge difference to how you manage your remote workforce.

And then for affiliates and affiliate managers. Diana and I talk about the nuances of managing an affiliate channel through a bankruptcy of the advertiser. There are some unique things you need to understand and rough waters you need to navigate, and Diana does a great job of laying those out.

You can connect with Diana on Instagram – littled99, LinkedIn and Facebook.

About Our Guest


Diana Gee-Calingo


Diana manages the affiliate channel for all Tailored Brands companies including Men’s Wearhouse and Jos. A. Bank.



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Top Tips

Diana reminds us the importance of ultimately saying yes. At the beginning of the podcast, Diana discusses how she made her way into the industry of affiliate marketing. The biggest takeaway was her suggestion of saying yes to new opportunities and being open to different options that could lead you to your dream career.

Create a dedicated workspace when working from home. Diana explains that early on in her remote life, she was working from basically any part of her home – living room, kitchen table etc. She mentions she was distracted, unorganized and even lost items. Once she had a set space, it changed everything. She also doesn’t allow herself to do household chores until outside of her workday hours to help create boundaries.


Retail vs. lead generation – was there a big learning curve?

“I think it was learning the different dynamics of that side of marketing… I used my personality and background in affiliate marketing to develop new relationships with new publishers that had a different focus. I had the knowledge and foundation to transition, and I was always willing to try something new.” 

Diana discusses how the past year has affected her affiliate program work.

This year has been really different. The program was paused for two months, so I basically had to restart the program. It was difficult to get it back to the level it was before, and I was trying to get the publishers back on board. It’s still been a struggle, and with the pandemic people haven’t been purchasing as much which is hard on sales numbers as well.”


[17:15] – “It’s important when you are fresh out of college and learning new things to just say yes. When you are young, you can pick up things more easily. Nowadays, I don’t think I could pick up things as quickly. Before, I could say yes and read or research and figure it out. The best thing to do is just say yes, it gives you new opportunities and open doors.”

[26:03] – “Work is different than school, but it’s also similar in the way that you interact with people. You have to have good relationships, especially when working together on projects. It’s still hold true now as a manager, you have to be on good graces and get people to do the work.”

[38:10] – “For the past year, we have been on quarantine working remote. Everyone is now used to the ebbs and flows of someone’s day but people are still different. I try to block time in off in my schedule so people know what my general day looks like. Some people like me like to start their day early when it’s quiet… I find that spreading out my day helps so you don’t feel rushed to get everything done.”