Title: Senior Director, Sales Operations & Strategy
Location: Chicago, IL
Preferred pronouns: She/Her/Hers
We never know what hair color Ashley will surprise us with next, but we can always count on her to add color to the Groupon world in more ways than one.
Tell us about your job! What do you do? What does a typical day look like?
I love to bring structure to the chaos. I like to be the problem solver for new and different challenges. I like to make a big impact. The great news is that I get the opportunity to do these things every day in my job leading Sales Operations & Strategy. My main responsibility is to set the local and enterprise sales teams up for success – this includes leading teams responsible for Sales Rep Analytics, Communication & Recognition, Sales Transformation, Lead Management, and Sales Training & Enablement. A typical day for me includes a lot of meetings with our key business partners (finance, HR, product, compensation, sales leaders) as well as significant time spent with my team on their major projects or development conversations.
What inspires you?
While I can’t say I’m a big fan of the movie, the concept of “Pay it Forward” is a major source of inspiration for me. I’ve had a significant amount of help and support from previous managers and mentors in my career, and that’s helped me to find my own career advancement and fulfillment. It’s not often that you can return that favor directly, so I look for opportunities to pay it forward to other upcoming leaders. Mentoring, coaching, and developing are extremely important to me. Some of my most rewarding moments are delivering promotions to those who I was able to help.
What was your first impression of Groupon as an employer?
I had a college friend who worked at Groupon who referred me for a position here. We talked about it one night during dinner, and two weeks later I had an offer in my hand. I couldn’t believe how quickly it moved – and that speed was the first impression I had of Groupon. Things move quickly here, and that was great for me. Let’s cut through the red tape and get things moving!
How does your work impact Groupon’s mission of building the daily habit in local commerce?
The Sales team has a significant focus on putting our merchants first. We want to make sure we’re helping them to grow their business through acquiring new customers, bringing them in during down times, or increasing repeat traffic. My team works to make sure the folks who are on the front line with those merchants have all the right equipment, processes, information, and insights to have meaningful and productive conversations.
What was your first role at Groupon and how did you get to where you are today?
My first role coming into Groupon was a Senior Strategy Analyst in the City Planning Department. I was tasked with working through the best deal structures for the hot new categories in the market. (Toenail fungus removal was a big hit at the time – eww!) After about six months, I moved into a Manager position in Operations. Although I had never worked in an operations position before, it was a really exciting move for me, and I found my niche. I’ve moved through the ranks in the team as a Manager II for Tools and Process Improvement, a Senior Manager, Director, and ultimately now the leader for the department as a Senior Director.
Have you won any awards in your time at Groupon?
Externally, I was recognized as a part of the 2021 Top 100 Revenue Operations Leaders list. This was a really exciting accomplishment to be acknowledged for my work within my peerset.
Within the Sales Operations team, we have our own form of recognition in the form of a tacky green blazer that we pass around once a week to a deserving member of the team. (Think the green jacket from the Master’s, and since we’ve been remote, this has turned into a virtual jacket.) I was awarded this one week for the support I provided the team during a challenging period. It was a fun achievement to be recognized by the people you lead. Even better – I was able to join the bulletin board of previously recognized colleagues.
Where were you before you joined Groupon? What brought you here?
I previously worked in marketing for a financial services company before joining Groupon. It was a great place to start a career, and I realized at one point that I was ready for my next challenge. Groupon was a welcomed change of pace as well as a place I could significantly increase my scope of impact.
“The teamwork, collaboration, and team culture we have keeps me coming back day in and day out. It’s so important to us that we’ve developed a set of team values that we revisit every quarter.”
What do your parents think you do?
This quote comes directly from my parents, “Well, we are not exactly sure what she does, however, this is nothing new. After she turned 5 years old, we have asked the same question on a daily basis. All we know is that she is gainfully employed and that is what is important to us in our “Golden Years!”
What’s the most interesting thing about you?
I have dyed my hair every color imaginable while working at Groupon. This includes the more conventional colors: blond, brown, red, black. I also explored the full rainbow: magenta, orange, yellow, green, teal, blue, and purple. I don’t know many places of employment that would be as supportive of Groupon in my hair identity exploration. For the record, I’ve settled on red for now.
If you could do another job for just one day, what would it be and why?
I would work in Talent Development – I’m super passionate about people development, and I love the feeling of making an impact on an individual. Whenever I get a chance, I like to host Project Management training sessions to share tricks of the trade I’ve picked up along the way.Are you active in any BRGs (Business Resource Groups) or Groupon Volunteers Yes, Women@Groupon and Allies! A few years ago I served as the Chair for Women@Groupon. I put a renewed focus on providing training and development opportunities for up and coming women leaders. It was also a chance to expand my network to other women in Groupon across departments with which I normally don’t engage. It was a super rewarding experience, and it helped me to grow my leadership skills in preparation for the next steps in my career. What’s your favorite local business?
My favorite Groupon I used was for Chicago Helicopter Experience. I bought two tickets for a helicopter tour of Chicago, and I brought my dad along as a Father’s Day present. I thought I was going to be scared out of my mind the whole time, but it as single-handedly one of the most fun experiences of my life. We took pictures and smiled the whole ride – to the point our cheeks hurt. Once we were done we went on and on about how much fun we had. I will never forget that day!
Your role probably exists at other companies, so what is it about Groupon that keeps you excited to come to work every day?
In talking with peers in Sales Operations at other companies, I realize how “cutting edge” we are in regards to processes and tools we use with our sales team. Our agility and ability to get things done ranks with some of the best organizations out there. At the same time, the team work, collaboration, and team culture we have keeps me coming back day in and day out. It’s so important to us that we’ve developed a set of team values that we revisit every quarter.
What advice do you have for someone interested in joining Groupon?
Groupon is a fantastic place to build a career. Whether it’s through internal mobility or providing experience and responsibility at an earlier point in your career than most other organizations – take advantage of it!
Rapid Fire Questions
Chicago Chop House.
“Love Will Keep Us Together” by Captain and Tennille.