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How to Attract, Hire and Lead Sales Talent to Success [Interview with Phill Keene]

Forster Perelsztejn author on Overloop the sales engagement, cold email, and LinkedIn automation software blog
Forster Perelsztejn Nov 21, 201710 min read

Welcome to the first interview of a series I'll be conducting with a few of the best salespeople around!

In this first episode, Phill Keene, VP Sales at Costello took some time to discuss the essential roles of a sales leader, how to recruit the right people and how automation done wrong can hurt your sales.

Let's dive right in!

Hi Phill, thanks for taking part in this! Could you introduce yourself a little?

Yeah, my name is Phill Keene and I run the sales team at a company called Costello! We create and sell a technology that manages deals along the pipeline. It can be used at any point, from an SDR phone call that qualifies all the way to that final close of having a contract discussion.

So the idea is that we want to guide you through calls, so when you get on a call, we want to make sure you’re following your process and the methodology you use for sales to capture the right information and then feed that back to your CRM to give you the ability to see any gaps in the deals that are being worked. And then we provide analytics to tell you what’s working and how to make it repeatable.

You took your position at Costello fairly recently. Given all the opportunities you had, what made you want to work at Costello?

Part of it is the team. I think the team’s great and they’re building an amazing product and I saw it quite a few times before I actually joined the company. I think that what we’re solving is necessary for the market.

If you think about the world of sales, things have been going faster and faster and it’s easy to send a lot of emails and communicate a lot. But the human element breaks down because we’re now managing more opportunities, phone calls and conversations than we ever have before. So you still need to slow down and make sure you’re still following your process and saying the right things when you’re on a call.

I saw the need for it, I love the product and I can really see myself being a user and I wish I had it for many years now.

So believing in the product is central to you?

Absolutely! And in this case I think it’s great, and the team on top of it makes it even better.

How many people do you work with in the sales team?

I’ve personally had up to a team of twelve people reporting to me directly. Right now we have SDR’s (Sales Development Representatives) and AE’s (Account Executives), with me leading the sales team and our CEO helping with the sales process.

How does your sales team acquire customers? Do you have a unified process?

We have an omni-channel approach. I don’t believe that cold calling, cold emailing or social selling are the only methods you can pull. I think it has to be a lever of all three combined.

Also, I believe in more of an account-based strategy. So we use a targeted approach where we know there’s a fit, so we’ve at least done some kind of qualification based off some kind of parameters that make me feel this person is the right person to talk to. And from there, we start reaching out and gathering information upfront.

I have a process: it’s called mapping. We figure out the right person or multiple people to speak to inside an organization. And from there we plan our sequence on how to actually reach them.

How much research do you do before reaching out?

We probably do ten to fifteen minutes of research when the companies are being identified.

These companies are usually set in certain parameters so we usually look at things like: do they at least have 10 people in their sales team? What CRM are they using? Do they have specialization? Are there SDR’s and AE’s inside their organization?

We look for people that already have some kind of sales training or sales process already built inside their organization. We look at layers: do they have a VP and a director or a VP and a manager on top of their sales team as well? Because these are good indicators that they already have a sales process built.

So we do that first; that’ll yield a few hundred companies. Then we research these companies individually and think of a specific approach for each of these companies after that.

How do you define your mission as a sales leader?

What makes me passionate about sales and sales leadership is that I want to develop people. I want the people who work for me to grow into someone I might work for someday. I’m a firm believer that a good leader can develop his people into better leaders than themselves.

How do you attract talent to your organization?

I think that, as a sales leader, that’s a good majority of your job. I’d say that 30 to 50 percent of your job is actually recruiting the right talent.

There are a few different things I do.

I lead a local networking group here in Indianapolis so I have a really good pulse on really top tier talent and access to those people. And, typically, those top tier, A type people know other A players that are in the market as well. Which allows me to build great relationships with them.

Also, I do a lot of networking in terms of taking coffee meetings; I consistently try to take at least one or two per week, whether it’s with other VP’s of sales or AE’s that enroll or SDR’s that just started their career and need advice to get started.

This is something I get a lot from.

I know which organizations train their people well. So when those people are ready to leave, I already know that they know how to do sales well. I also get access to people and build a really personal relationship, and I don’t walk into it with an agenda. I try to be generally helpful and that will yield, over time, good results in terms of them looking to work for me one day.

Putting content out there is important as well. I had my own podcast, I’ve written a lot of blogs, I’ve been pretty active in the sales community at large, not just here in Indianapolis.

I constantly try to keep myself out there and stay top of mind and I think that your personal brand as a leader is what will attract talent to you as we go into the future and millennials become a greater part of the workforce.

That’s a good point, we have more and more millennials entering the workforce! How do you think things will be changing? Do you keep an eye out specifically for millennials?

Well, I think there’s something to be said about having a really well-experienced sales person in a company and I think they help mature the organizations so it just depends on what your needs are.

As a tech company, often times you’re going to hire slightly younger people since they’re the ones who are attracted to work at your company, so I’m constantly recruiting in that “world”.

But at the same time, it still takes some people that are pretty experienced, that have been through the wringer a little bit and can help guide your younger reps.

What are you looking for in potential hires?

The demand for competent salespeople is important and I look for people that are self-learners so they’re willing to put the time and effort to get better on their own. That’s critical, especially at earlier stage companies. You need people that can go and figure it out on their own and that’s hard because you still have to guide them and get them to do the right stuff. So that’s the first thing I look for.

Secondary is I look for people who are magnetic. And what I mean by that is when they walk into a room, people are drawn to them. Typically those are high-performing salespeople. They have some kind of personality, some kind of charisma that makes other people want to be around them. Those are the type of people that are usually successful in sales.

I also need someone who I can help through the process and work through doing things well. Especially when it comes to using Costello because that’s what we do, we help build the process of sales on top of that so we hire people that are good at building relationships and are good at communication and then we teach them to process. So if they’re self-learners they can definitely do that well.

What is the most common reason you turn down applications?

We sell sales tech to salespeople so we need them to be very good at communication and be confident in their answers. So if they lack confidence, that’s something where they’ll be hesitation for me right away.

Also, I try to have a conversation about money, of some sort. Often times, especially when they’re young in career, a lot of people have a tough time talking about money but, unfortunately, it’s part of our job. So if you’re not comfortable talking about money, you’re probably not going to be a great success in sales.

Other than that, I’ll ask them about situations where they’ve been challenged and had to fight through it. And even if you’re an SDR that’s just coming out of college and it’s your first job, there’s got to be some kind of hardship in your life you’ve had to overcome. And if you never have, the first time you hit a low in sales, it’s going to be really difficult.

Do you think that colleges and universities generally do a good enough job teaching students about sales and negotiation?

No, not really. I think that here in the US you only have 127 universities that actually have a sales program. Considering there are thousands of universities here, I believe that’ a problem.

They don’t really teach you the basic skills of sales like opening up dialog, having a conversation… I was fortunate to go to a university that had a sales program so I’m still able to apply a lot of things I learned in college to my real life today.

You wrote in an article that sales teams had a tendency to become enslaved to automation. When is it too much automation? What should you automate? What shouldn’t you automate?

The biggest problem is that people try to automate things when they don’t have a process. Unless you have something structured that already works fairly well before putting automation on top of it, you’re just going to accelerate things that are broken.

So if you’re bad today at having good conversations and then you accelerate that and have hundreds of conversations, you’re still gonna have bad conversations. You have to find something that guides you through those calls and makes you follow everything right so you don’t end up in a place where you don’t know what you’re talking about.

If you’re not closing deals at a high enough rate today, let’s say your close rate is 5% and all of sudden you add 3 extra pipelines, you’re still going to close at 5%, and maybe lower because you can’t focus on things.

People want to accelerate because they think that volume is going to fix things, but it just doesn’t. It’s a fundamental flaw of sales in the world today.

What’s your sales stack? What tools are used at Costello?

We use ZoomInfo for data, we have SalesLoft for prospecting and sequencing, and then we have salesforce.

Aside of that we have few other tools: we have Datanyze that helps us pull technographic data, that helps us do screen shares, an e-signature provider called PactSafe and, of course, our own tool, Costello.

You used to write a lot of content on LinkedIn and you’re still pretty active on the platform. You did a podcast with David Dulany and now you’re talking with me. How important is it to you to take the time to talk, exchange and share with other professionals?

It really is important. I believe -and even we as company believe- that sales reps are going to disappear. Sales reps are not going to be a part of the sales world in the very near future. Sales professionals, on the other hand, are going to be around for a long time.

People like that think that this is a craft and believe in sales and getting better at sales. At Costello we firmly believe that we have to share the knowledge that we have and get people out there to understand sales better. If I can help just one person get better when I talk with them, it’s definitely worth it.

We believe sales to be a profession and a craft and we want to share a message. We think it’ll help people.

What’s the best sales advice you’ve ever received?

That’s a good question! The best sales advice I’ve ever gotten and my favourite one to give is that you should communicate in sales the same way you would communicate with people in general.

So you can’t automate everything, because if you speak to everybody, you speak to nobody. You need to really talk to people on a personal level when you’re building your sequence and your cadence. You need to build it as if you were talking to your mother, your boss or your friend who’s living down the street.

I have a cadence called the Crazy Ex Cadence. Typically, what happens in prospecting cadences is I’m going to hit hard upfront for three or four days and then I’ll trick a lot and nurture over time. That’s not the way we communicate. I like the Crazy Ex name because it’s funny and sticks in people’s heads.

But really, if you think of anybody you have a relationship with, your boss or someone that works with you. They’re going to send you an email and then they’re going to give you some time to respond to that. And over time it becomes more and more frequent.

That causes a sense of urgency and you feel like you have to respond because that’s how you communicate with people you respond to.

So whenever you’re doing anything, whether it’s sending an email or talking on the phone or building a sequencing cadence, communicate like you would be communicated with. And communicate the way that you do with anybody else in the world you talk to and have conversations with.

That’s my best piece of advice I’ve ever gotten in sales. And I’ve carried that now through anything when it comes to sales.

Okay then, that’s a lot of great information! Thanks a lot for doing this!

Absolutely! Anything you need, just shoot me an email!