Successful women in sales

Successful Women in Sales Make The Leap and Own The Risk

Every path comes with its opportunities and risks. When you choose one, you have to make sure your eyes are wide open and you know what you’re walking into.

A key ingredient to guarantee success in sales is confidence. The internal perception of how we see ourselves is an important factor in affecting our career ownership and what lies ahead. 

Here’s my advice to each woman who wants to succeed in a sales career path:

1. Take risks and make the leap 

You start to get comfortable when you know you are in a company that’s doing well and you’re secure. After my third promotion, I knew it was starting to feel like a cog in the wheel.

I was only 26 and I remember thinking that I’d keep going up if I stayed here. Moving up felt so much like a ladder with so many rungs and I didn’t want to get stuck in that. I had to decide whether to stay with that security or take a risk.

I always knew from my first year in sales that leadership is where I wanted to be. There was a manager role I was ready to go for. Our CEO at the time at Zendesk said: “90% of the top salespeople suck at sales management, so just know that. Make sure you are ready to make the leap because moving from an individual contributor role to manager is a major change.” I knew he was right. I wasn’t ready to do that yet, but the role I wanted wasn’t there, and so I had to make one. I identified an opportunity for a group of accounts that were not being focused on by my organization. It was another risk that paid off, but it also taught me that it was okay to slow down the jump to management. When I took the time, I felt like I knew I was ready when I actually made the move.

That risk paid off, but I did it knowing full well that it might not. I think that was the most important part. I was okay even if it didn’t end the way I was hoping it would. I went in knowing that I was making that leap. 

2. Set your goal and work to reach it

If you want to be a leader, shadow your own manager. You should own your future success in that role. This is the first step in taking ownership of your career and your development. Ask to join in meetings. Ask what it’s like to put together a forecast for a team of people. Make sure that your eyes are wide open and you know what you’re walking into. 

There are so many great female sales reps. Their confidence gets stuck in a gap where they lack belief in their ability to lead. It’s more natural for people to point out a male sales rep and offer to move him into management. On the other hand, this might not happen as obviously with women. Women might feel like they’re doing really well but prefer to stay in their comfort zone rather than setting that goal and working to reach it. 

3. Recognize when risk is an opportunity

The most important thing when taking a risk is not to limit your thinking to your career and your job at that moment, but to have an overall idea of what you want and think ahead. 

A conversation that exemplifies this was one I had with a woman who just had a baby and wanted to figure out her next step. She’s one of the best salespeople I know and a great leader. I saw in the conversation the internal struggle she was going through. She wanted to progress her career, but at the same time, she wanted to be there with her child. She didn’t know what the right choice was. I think what comes with that is being okay with not knowing and giving yourself time to sit with it and trusting your own instincts.

4. Own your success and failures

I help my reps and my managers to not be afraid of failure. It is actually a good thing, because it means that you have learned what not to do the next time and how to get better. Don’t be embarrassed about it and don’t beat yourself up. There is no problem if you’ve lost that deal. You’ve learned what you’re going to do next time to win.

Ownership is recognizing your own success in that role and proving to everybody that you’re willing to take that on. You can have someone guide you through how to better own your career, as it can be hard to do it on your own. I wouldn’t have reached where I am today without those mentors who paved that path for me. Mentorship is crucial for progress. It is making sure that you surround yourself with great people who can encourage you, push you, tell you that it’s okay to fail, and then teach you how to succeed in all the right ways.

5. Gain credibility by being vulnerable 

If you are vulnerable and if you are real with the people, you will never feel like an imposter because you’re being your true self. I have imposter syndrome all the time. 

One of the first times I experienced imposter syndrome was when I started as a manager. I had never managed and my team knew I was not experienced in management. I had been working in enterprise sales, but this was a corporate sales team. It was a very different sale and I was terrified of how I was going to make these people see me as a leader versus just another rep that they’ve seen on the floor.

I definitely think as a manager (I especially recognize this now that I am someone who has managers reporting to me) you can never do it alone.

And I think you feel like an imposter when there’s something you’re trying to compensate for – whether that’s lack of experience or confidence or some other factor that’s limiting you. You might find yourself saying, “I’ve never done this before, so don’t tell anyone. I’m just trying to make it work.” However, the attitude you should take is, “I’ve never done this before. I’m figuring it out as I go, but what I can tell you is that I’m a really good salesperson. Let’s close some deals together. Once we do that, then you will see the value I can bring and how I am going to work with you as a leader.”

I believe you gain credibility and respect when you say, “I know I’m not perfect at everything. I know there are things that I have to learn and to get better at. I’m aware of those gaps and I will get better at them. I’m also asking you to hold me accountable for them.”

It’s easy to look back and understand that certain risks and challenges were essential to progress to the place I am in my career today. From this experience, it becomes clear that you can have successes and failures, embrace vulnerability, and own the opportunities that are important to you as you navigate your own career. Remember to have confidence and be open to how your journey will unfold.