Ashley Stennis

I attribute my success to a handful of things, but it really starts with grit and determination. I grew up in a very non-traditional manner - farming with draft horses, living off the grid until I was a teenager, and then my parents continued to organically farm. It was really hard work, we were quite poor, and we had to work incredibly hard. But that upbringing taught me grit and determination, and I'm not afraid of hard work. To have gotten through college on my own, working three jobs, and then to have made my career - it was hard, but I was determined. Without that kind of grit, I would not have even had a chance to develop the other skills that have been hugely impactful. The other thing is my integrity. I always want to be my best version, and I am always willing to help others around me. One of the things I find most fulfilling is being able to lean in and help, whether that's my team or other teams. At Shopify, as I was growing out my skills in AI, I was the AI power user for the mid-market sales team. In Q2, I was ahead of the curve as far as how our 50-person team was using it. I did workshops, I did one-on-ones, I helped people set up the tools, I created enablement tools to simplify it. That's something of value to me that I hold dear.

The best career advice I ever received was from my mentor, Jeff Bunkin, when I was an SDR. I had been offered an SDR manager role, but I also had the option to be the first SDR promoted within the company into an Account Executive position, because it was a startup. I met with Jeff and asked him what I should do. He looked across the table at me and said, 'Ashley, you would be an absolute idiot not to take the promotion into the sales team. You're born to do this.' I said, alright, I mean, that's pretty dang clear. So I took the promotion, attached myself to his side for the next three years, and learned everything I could. Honestly, everything's compounded on that, so I credit him with my career and where I'm at. Whether I continue in tech sales or do another kind of role within tech or start my own thing, it's in large part due to him. I received a lot of good career advice over the years, but I wouldn't be where I'm at today if it wasn't for him sitting across that table telling me that.

My advice for young women entering this industry is to really take the time to understand who you are and where your boundaries are. First, nothing's going to be handed to you - that's just the case for the workplace in general as a woman. You really have to, unfortunately, stay involved in office politics, because your work is important, but it's not the sum of how you're going to be determined for promotion. You have to be involved in the politics and all of that that goes into it. Lastly, find good mentors really early, at every level. I did a leadership course once that broke down the coach, champion, and stakeholder model. Basically, it's not enough to have your manager as the person pushing for you. You need to invest in having relationships with people at the director level and the VP level if possible, because your manager can advocate for you, but they're not the one making the final decision. You need a champion at that level that's pushing for you. And even better if you have somebody on the executive level that's determining the budgets. Get as much exposure as you can possibly get - that's what's going to shape your career.

The biggest challenge in my field right now is the fact that AI is changing how companies and jobs look, and how they operate, quite literally on a daily basis. In my time at Shopify, things changed almost daily, and that is not an exaggeration. That's not the case for every company - Shopify is a publicly traded billion-dollar company, so they're moving even faster - but it's coming at various levels, and that is a huge challenge. It's also a huge area of opportunity for somebody who is able to be agile and adapt quickly to set yourself apart. The people that are going to get left behind, especially in sales and tech in general, are those that are resisting. Now is the time to be involved and to shape how AI is used and how it's responsibly used within companies and within your role. I think it's the opportunity of our generation to really set ourselves apart, because as millennials or younger millennials and Gen Z, we have come up against the 2008 crisis, we graduated into a rough market, we had COVID, now we have layoffs and a somewhat volatile economy, and we have AI. Most of those things have worked against us, and AI is certainly doing that as well in how it's getting rid of jobs. But now is the opportunity where, if you get invested and you learn how to do it correctly, it can actually set you apart. I want to stress the opportunity to determine how it is used responsibly - I am not a proponent of just letting the brakes loose with AI everything, because it can be used so poorly.

Integrity is a huge value for me. Working in sales, there's obviously a certain reputation that comes with that - that you're going to do whatever it takes to get sales, whether it's a good fit or not. My parents are small business owners, I grew up in that atmosphere, and my sister and brother-in-law are too. I know the impact of a bad or a good decision on a business. Integrity and being able to sleep at night and feel okay with myself in the work that I've done, the sales that I've closed, the people that I've worked with, and those that I've told 'hey, this is not the right decision for you right now' - that's the most important thing to me, genuinely. The other thing is being honest and showing up to work as who I really am and my best version. That means being willing to take feedback, and also being able to push through the discomfort of giving feedback in a professional and respectful way. I try to keep my values for work and personal life as close as possible, but in my personal life, those that I love are the most important things for me. Genuinely, nothing else really matters. My career, my success, what I do in this world, doesn't really matter if I don't have the people that I love and care about, and that I know that I'm showing up for in the way that I want to for my family.