Expert Advice to Guide Your Sales Career Path

It’s a common trajectory: do one to two years as an SDR and then become an AE. But what if your career path in sales looks a little different?

In our latest episode of The Closing Show Live, we sat down with Kristen Twining, the SVP of Global Sales for Illusive, an enterprise cybersecurity solution for preventing ransomware and other cyber attacks.

Kristen's had an uncommon career trajectory, transitioning straight out of college into a field sales role, and then going somewhat backward to work as an SDR before becoming an inside sales director and ultimately a senior vice president.

We asked her what makes a great AE, how to get a job as an AE, and how to transition into senior management.

Kristen loves being mentored and mentoring others. Keep reading for her hard-earned advice, or watch the full interview here.

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How to land your first Account Executive role

Ready to start closing deals? Read Kristen's best advice for moving up the ranks.

1. Know what makes a great AE

Call it grit. Call it hunger. Call it hustle. Whatever you want to call it, it matters. A great AE is excited to keep improving and earning higher commissions.

“When I look for a great AE, I want someone who’s got that grit. I want to know that you’re hungry.” - Kristen Twining

2. Shadow the AEs you work with

Find ways to learn what AEs actually do. Ask your AEs if you can shadow them on a couple of calls, and see if there are any internal meetings that you can sit in on occasionally.

This will showcase your determination—making it likely you’ll get snapped up for an AE role quicker, and what you learn during those shadow sessions will make the transition smooth.

3. Be prepared to work the middle of the sales cycle

When you leave your SDR role, you’re also leaving behind the beginning of the sales cycle. You won’t be prospecting nearly as much. Instead, you’ll spend the bulk of your time in the middle of the sales cycle, so be sure to focus some of your professional development on that area.

“It’s the middle of the sales cycle where I see AEs having the most difficult time. It’s a little bit of a shock when they didn’t realize it was this hard.” - Kristen Twining

What AEs should be learning from SDRs

When AEs are using the “land and expand” method with their current accounts and progressing leads through the middle of the cycle, they lose some of their prospecting muscle.

Kristen says that AEs should take a page out of SDRs’ books by keeping up with best practices around prospecting (and making sure to do at least some of it themselves).

“You have to continue to prospect, and you can’t just say ‘I’ve got an SDR who’s going to do that for me’. You’ve got to be able to make connections with new people and sell different pieces of your portfolio.” - Kristen Twining

How to transition from an AE to a management role

Do you have c-suite dreams? Here’s how to make that first jump from individual contributor to manager.

1. Get more specific with how you want to help others

When hiring for management roles, Kristen often hears people say they want to help others, but that’s not specific enough. Get clearer on how you like helping others, such as mentoring them on their career path or helping them identify their weaknesses.

You also need to recognize that management isn’t just about people. It’s also about data.

2. Be prepared to be data-driven

If you don’t like data, you’ll hate being a manager.

Everyone wants to chat strategy, but the truth is that it takes data to get there.

“To be the one who sets the strategy and the vision, you’ve got to have data and trends. You've got to understand where to take the business based on where it’s been before, and a lot of that gets missed when you think about going from an individual contributor role to a leadership role.” - Kristen Twining

Look for opportunities to build your muscles when it comes to organizing and analyzing data. Learning how to use data management and board portal software comes in handy when working with those in higher positions.

If all of that doesn’t excite you, then you might not actually want to move into management, and that’s okay.

3. Focus on operational excellence

Become obsessed with processes and operations.

Take a growth mindset when it comes to updating the processes that you and your fellow AEs use, and this will pay off when interviewing for a management role and when tackling your first few weeks on the job.

“You’ve got to be operationally excellent to be successful, and once you get into leadership that becomes so much more evident.” - Kristen Twining

The best career advice no matter your trajectory

Everyone in sales has their own career path, and it’s not always linear. No matter where you are in your ladder-climbing (or zig-zagging), these smart tips will help.

1. Get crystal clear on your goals

Now it’s time to geek out. Knowing your career goals is good. But writing them down is so much better.

“I write my career goals down. You have to have something concrete and know what you’re working towards. Then you can almost control your destiny and know what you want to say ‘no’ to and what you want to go after.” - Kristen Twining

As you learn more about what you love doing and what you hate doing, you can continue to refine these goals.

2. Build a network of mentors

Everyone knows that mentors matter. But how do you get mentors? The truth is that you already have former bosses and colleagues that would love to help you. You need to keep these relationships alive—and give as much as you take.

Celebrate their wins, stay in touch quarterly, go out to lunch when possible, and find more ways to stay connected in person and online.

“When I stepped into my current role, there were some things I had to work through really quickly and I am so thankful for my network because I picked up the phone and called three people immediately and said I need your help. And each person helped me talk through my decisions.” - Kristen Twining

3. Ask for help

It’s okay to show your vulnerable side. You’re not supposed to know everything right away. The sooner you accept your imperfections, the better.

“My downfall early on in my career was feeling imposter syndrome, not asking for help, and falling flat on my face.” - Kristen Twining

4. Validate your assumptions

Before you pat yourself on the back for landing a role you might end up hating, make sure to take a step back and test your hypothesis. Do you really want to do this? Courses and certifications are one of the best ways to find out.

“I had a feeling that the SVP / CRO role was right for me, so I took a Pavillion course, and I was like, Yes, this is what I want to do. You’ve got to keep validating that you are, in fact, on the path that you want to be on.” - Kristen Twining

So, ask yourself, what do you really want? Then shadow colleagues in that role and take courses to make sure you’re certain. When you’re clear on what you want, go for it.

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Expert Advice to Guide Your Sales Career Path

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