Sales

Ask a Leader: Interview With VP of Sales Kyle Parrish from Mixmax

November 16, 2022

Written byRita Melkonian

Ask a Leader: Interview With VP of Sales Kyle Parrish from Mixmax

Interview with Kyle Parrish, VP of Sales at Mixmax

About Kyle: With over 20 years of experience in sales, Kyle has been leading and developing high-performing sales teams for the past 14 years. He started his sales career in large organizations like Oracle and Google, and then he moved over to the startup realm to be a VP of Sales in 2015.

In this interview, you’ll learn about what some of the biggest challenges are as a sales leader, how to organize a sales team, how to keep your team motivated, killer coaching tips you can use asap, resources you can learn from, and career advice for leaders who want to make a real impact.

1. What has been your biggest challenge as a leader?

The biggest challenge of a leader is always focusing on things that have the highest impact and prioritizing those first. And that can be difficult to decide because leaders are challenged with things every day that are urgent and need to get done, but that don’t necessarily have high impact. And so that gets in the way of taking on these big challenges that actually move the needle. 

And I think remembering that the job of a sales leader, especially the top officer in the company, is to make sure that they are prioritizing things that have the highest impact and the biggest leverage points. 

Experience and cross-collaboration are what will help you dictate what those things are. You can work with other partners in the organization like marketing, customer success, and even product to help identify those things. And really focusing on those has always been the top challenge for me as a sales leader.

2. How do you organize your sales team?

We organize our team fairly traditionally. We have inbound SDRs that are specialized in what marketing delivers to them. We have outbound SDRs who are going after our ideal customer profile. And then we have account executives that prospect for their own business as well as take inbound leads from our inbound SDR team and outbound leads from our outbound SDR team. 

We have two different flavors of account executives: one that is focused on the mid-market, and every company defines its mid-market slightly differently. We start our mid-market definition of 500 employees, which is pretty low for most organizations. And then we have account executives that handle the SMB. 

Mixmax is slightly different in that we focus on small and medium-sized businesses, and so that is our target persona. We don't generally go after enterprise businesses–that's just not who we do well with. And knowing that–knowing who our ideal customer profile is–is what influences how we set up our sales team.

3. How do you keep your team motivated?

Ideally, you find account executives, SDRs, everybody on the sales team who is self-motivated. Now, it is tough to stay motivated in the face of so much rejection in the sales team. 

And so what I do with our sales team is remind them that it's not a sprint, it's a marathon, and that there is going to be some rejection. There are going to be some hard times, but they have to keep their eyes on the prize and on the goals that they’ve set for themselves. And for us as a sales team here, remember that each individual has a gigantic impact on the outcomes of every month and every quarter at a startup. 

We're only a 75-person startup. And so the 12 or so people on the sales team have an outsized impact on the things that they do every day. And so reminding them that the results that they put up on a weekly, monthly, or even daily basis impact the entire company and our goals as a whole company.

4. What's a killer coaching tip you can share?

I'm going to cheat and say that there are two killer coaching tips that I want to share. And they're sort of related to one another. 

The first one is situational leadership. It's not necessarily a coaching tip, but each individual is motivated individually. And for the sales leader to know what motivates each individual is so important in coaching them and helping them get to the next level, whatever that may be.

It might not even be a career in sales; they might want to go do something else in their career. But to know that, keep them motivated, and coach them along that path and how they can get there, will keep them doing a great job for you. 

The second one is radical candor. And if you're not familiar with the concept, radical candor is telling people exactly what they need to hear, but doing it in a kind and humane way with empathy. So it's not being a jerk and just saying it flat out. But it's also not putting it so softly that they don't get the message. 

Radical candor is that everyone should understand their strengths and weaknesses, where they need help, where they're doing great, and where they can help others. And to just tell them that so that they can grow.

I don't think people grow when you try to be too soft with them or be too hard with them that they will shut down. You need to tell them exactly what they need to know in order to grow as a coach and a mentor. But to do it in a kind humane way, and then offer to help them along that path. 

This isn't a solo mission to go improve–you don't just tell somebody the coaching tip and have them go do it. You coach them to actually make them better along the coaching path that you have for them.

5. What resources would you suggest for new sales leaders?

New leaders have so many resources available to them. Some of them are free resources like LinkedIn. And there are a lot of sales leaders who are giving free advice on LinkedIn now. Can you learn how to be a great sales leader just by reading LinkedIn? Absolutely not. But it is a great resource. 

There are many free webinars where people share coaching and leadership tips. I highly recommend attending some of those even if they're paid for. Ask your boss or your employer to pay for those things and go attend them. I'm not saying that this needs to be a five-week on-site seminar. But it might be a coaching webinar that is a day long. 

I also highly recommend reading books, educating yourself on what great leadership can be, and then adopting that to your own style. You can't just be a sales leader that somebody else says you should be; you need to adapt it to your own style. But actually taking the time to do professional education on your own is super important. 

There are some great books about sales leadership out there. Mike Weinberg comes to mind. He’s what I think is an amazing sales writer; somebody who's had a lot of success in sales and writes about it in what I think is the right way.

6. If you could go back in time, what advice would you give yourself?

The advice I would give myself is to get into startups earlier. This is a personal thing for me. I started my career in big companies–I started out at Oracle, then went to Salesforce, then back to Oracle, and then to Google. Those are some of the biggest software companies in the world. 

But then when I started working for startups, I found that my impact on a day-to-day basis was so much more. And I enjoyed that feeling. I enjoyed knowing that the things that I was doing every single day, and the decisions that I was making on a daily basis, had an impact on the business, and to see them grow. 

That was what really motivated me a lot more to do a really, really great job and to learn and expand my skill set. That's not the same thing for everybody. And so that won’t resonate with everybody who's listening to this. But for me, that was it. Get to startups earlier and have a bigger impact on the work that you do on a daily basis.

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