Brandee Winstead

This week I caught up with the brilliant Brandee Winstead!

Brandee is Customer Success Manager at Live Your Message, a business training company specialising in helping online entrepreneurs. Brandee has been there for just five months, and this is her first leadership role.

Hi Brandee! Thanks so much for telling me your story, particularly since you are new to leadership, and a lot of those early challenges are still fresh! How did you get into Customer Support?

I was working in neuropsychology for ten years. It was my dream field and I even got my dream job – training monkeys to play video games to study learning and memory. It was amazing!

…but it paid horribly. 

My only option for a living wage was to go to grad school. But after that, I wouldn’t be working hands-on with the animals. I’d be writing grants and begging for money. That’s not at all what I wanted to do. 

So after ten years of working in my dream field, I decided to move to tech. I initially took odd jobs with startups and found out I really liked working in Customer Support. 

When I moved back to my home city, Atlanta, GA, I took a student support role in a Neuroscience Affirmative Action program…but then we lost our grant. Suddenly I had no job. 

I had my eye on Mailchimp – they looked super awesome to work for. And with my determination, I got it! It was not an easy job to get. 

I quickly worked my way from an overnight Support Agent to a Specialist, then later to an Analyst because of my research background. 

What happened then?

During my growth at Mailchimp, it was becoming more clear that the fit wasn’t exactly right for me. I needed something with more personal connections. Mailchimp was just too…big! Too impersonal.

It’s hard to admit when a role isn’t a fit for you and you need to move on. It feels like failure, but in reality it is being true to yourself. 

I know my genius zone and I was not in it. My genius zone involves working directly with a team or users to bring success and support. 

So I found a job at an experience company. They hired me to build their Customer Success department. I’m now a Customer Success Manager at Live Your Message and I love every moment of my work. I supervise an awesome and small team, so I get to provide that more personal attention and care. I am also supported by the rest of my colleagues at a level I’ve never experienced! And with our users…well, I get to know all of them closely. It’s a much more personalized support avenue than what I experienced in SaaS. 

Has it been tough to make that move into leadership?

It has been a challenge, achieving authority with my agents who had already been at the company before I was hired as their manager. But I really think that compassion, empathy, attention to detail, and knowledge on how to deliver feedback can go a long way!

At my former position, I could not stand the management culture. I thought I would NEVER want to go into management with how I saw it handled before. It almost seemed cultlike and secretive. Like it was a religion no one else was allowed access to. 

And the employees were unhappy…they complained about management constantly. I just couldn’t imagine myself being in a position where everyone hated me and I couldn’t be honest with my reports. 

Turns out, leadership doesn’t HAVE to be like that! Leadership can be supportive, uplifting, encouraging. You CAN be friends with your reports.

You don’t have to operate like a secret society. You can lift up instead of push down!

And you know what? I LOVE being a leader. I love lifting up my team! 

When it comes to your team, how do you measure and ensure their success? Is it through the usual metrics?

I feel like metrics are good for larger support departments, but they don’t exactly fit mine.

Metrics are difficult for my support team, and quite unfair. We do more than just work the queue. We also support the internal team. On top of that, support volume varies wildly because our products are experience products and done on a live schedule. Like school! For example, we launched a course in March and were slammed. Now that its April, much less volume. 

Instead of metrics, I look at things in the moment.  How many projects and tickets were completed this week? How was your workload this week?  Then I can compile the successes of the past weeks and get a good feel of how an agent is doing.

On top of that, I have weekly 1:1s and also like to have a lot of fun with my team. I’m definitely the nice boss!

Do you have any good resources to recommend?

I stay involved with communities like Support Driven. They’ve always had my back and I adore them! I also develop skills with various online learning programs.

Last, but most definitely not least, how do you sign off on emails?

Onwards, Brandee

Thanks, Brandee! Great to hear your story.

Watch this space for another great leadership story next week!