HERstory: Courtney Rogin, former Head of Content, SaaStr

 
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Courtney is the Marketing Campaign Manager at Poll Everywhere. Previously, she led content for SaaStr's worldwide events, including SaaStr Annual, and held management roles at Mattermark and Gofanbase. Taking after her father, who has been a senior marketing leader for over 30 years, marketing is in her blood and has quickly become her true career passion. Courtney resides in California, where she spends her free time advocating for rescue dogs, reading, and enjoying red wine.

 
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How did you break into leadership?

I started as a social media coordinator at a digital marketing agency, where my main focus was writing content for clients. As our team grew, I took on training new coordinators on brand guidelines, writing for social media, and editing their first content pieces. We kept growing and the need for a supervising editor became available. Because of my training and editing experience, I took on the role. I led the team from editing to strategy to execution, learning what works and what doesn't along the way. The main thing I learned was to ask questions; ask if my superiors needed help.

 

What unique obstacles or challenges have you faced as a woman in a tech leadership role?

Something that’s fairly prevalent in tech, even today, is when an idea or opinion posed by a woman is discredited by her male counterparts only to later be revived by those same male counterparts as a great idea. Not only is it frustrating, but it can also discourage women from speaking up in future conversations.

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As an introvert, I already struggle with making conversation when I feel awkward or out of place. Being an introverted woman in a tech leadership role can be extra daunting, particularly in executive-level meetings, where hard decisions are being made and it’s time to make your voice heard. It’s much easier to remain quiet or agree despite having a different opinion.

I found it valuable to have a tribe (a group of friends and colleagues of both men and women) that challenge me to face my fears and push me out of my comfort zone. They keep me in check, support, and motivate me, but they’re also the first ones to encourage me to speak up! Even when I try not to listen to them... :)

 

How do you negotiate a higher salary?

Salary negotiations have always been a challenge for me personally—knowing when (and how to have the confidence) to negotiate when the opportunity arises. Using a high-level service, like Comparably, has been helpful for increasing my motivation and confidence to do so. I also like to come prepared with a recap of what I've accomplished within the scope of my role and the projects I’ve worked on outside of the scope of my role to help establish my true worth.

 
 
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How do you know when it's time to change jobs?

I’m only a few years into my career, and I've worked for a number of companies. One of my struggles is knowing when to change where I work. I'm still learning how to navigate this, but the one thing I always trust is my gut. My gut is rarely wrong, and when I do ignore it, I feel the consequences. I ask myself a series of questions as a "gut check":

  • Does something feel off? 
  • Do I come home from work exhausted?
  • Do I not want go in the next day? 
  • Do I get easily irritated with my day-to-day routine?

If I answer yes, or even half-yes, I start to evaluate what needs to change, which doesn't always mean quitting.

Always remember to keep your best interests at the forefront. It may seem hard, but if your current role isn't working and you've tried to remedy it, it may be time to start exploring other opportunities. It’s also okay to leave a role within the first year if it really isn’t a good fit and nothing is improving.

Talking to my closest friends and allies is where I turn when I've made that decision; they are amazing at weighing the options and help by asking the even tougher questions that are easy to ignore. 

 
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If you could do it all again, what would you do differently?

Be more confident in myself. Hands down.

There have been times where I've waived and hidden instead of standing up for myself. Because of this, people (even my coworkers) have walked right over me. Because I left my voice at home. 

What’s been the highlight of your career thus far?

Directing the content for SaaStr Annual 2018, the largest non-vendor B2B SaaS conference. I managed and selected all the speakers for three days and five stages of content. It's a year-long process, but it’s very rewarding to see the content come to life on stage in front of 10,000 of SaaStr’s community members. I had a really big diversity goal for our content, and I’m super proud to say that I secured a speaker pool with 65% diversity and 45% women in 2018.

 
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What's your advice for up-and-coming marketers?

My advice is to ask questions about things you don't know. I know that seems like a no-brainer, but we all get stuck in the weeds in what we're working on and can’t imagine taking on ‘one more thing'. That 'one more thing' could level up your marketing career.

For me, early on, that was learning how to write SQL—even though, at the time, it wasn't part of my role. You’d be surprised how many people would be more than happy to teach you how something works, or at least get you started so you can tinker, fail, and find success on your own. 

Also, stop second guessing yourself! It’s okay to make mistakes, try new things, and take the big leap into the unknown.

 

Share something valuable or interesting with the community. 

Adam Grant's Give and Take: Why Helping Others Drives Our Success changed the way I lead and work with others. I would dare say it should be required reading for anyone looking to break into leadership or simply just improve their career.