Episode 102: The Traits of a Good Prospector – Phill Keene

Predictable Prospecting
Episode 102: The Traits of a Good Prospector - Phill Keene
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What skills and attributes make for a good prospector? When companies are looking to hire prospectors, what traits are they looking for? Today’s guest has a good idea, and has had great success in hiring and training for his business.

Phill Keene is the Director of Sales at Costello. Over the course of his career, he’s had the opportunity to get familiar with every part of the pipeline. Listen to the episode to hear Phill talk about the importance of self-learning, how pattern recognition relates to business, and the hiring process that Phill uses to bring on new prospectors at his own company.

Episode Highlights:

  • How Costello got its name
  • How to get people to put time into mastering prospecting techniques
  • The importance of being a motivated self-learner in prospecting
  • The skills that a good prospector needs to have
  • How pattern recognition can help in prospecting
  • Phill’s success rate for hiring prospectors
  • Phill’s hiring process
  • How Phill determines which person gets hired for which role
  • Phill’s process for onboarding


Phill Keene


Phill’s Email: phill@ncostello.com


Marylou: Hi everybody, it’s Marylou Tyler. This week’s guest is one of those rare breeds that could cover the entire funnel and beyond. Phill has been pretty much in every position of the pipeline you could think of, or even haven’t thought of yet. I’m gonna try to get him to focus today on prospecting, since that’s what I know. But he is the man to go to to discuss things, even in marketing, probably sales ops.

Phill Keene is the director of sales at Costello. Welcome to the podcast, Phill.

Phil: Thanks for having me. I’m excited to be on today.

Marylou: When I first heard the word or the phrase Costello, I immediately thought of Abbott and Costello. Is there any correlation with your company name to that fabulous team? I remember when I was a kid, I was getting my stitches. I had an appendectomy and I had just come out of the O.R. with stitches. Abbott and Costello was on, of course I was cracking up so much that I burst my stitches and had to go back in and get restitched up. Tell us about the company.

Phill: That’s a great story. We’ll have to go down that route, maybe a different conversation one day. But, yes. Thinking about our websites and Costello, it definitely is alluding to the Abbott and Costello comedy duo from many years passed. Reason why we went down that path is we originally recalled a couple of different names as we were prelaunch. Originally, it was like navigate a call, navigate a deal, what’s the software.

Then our customers kept referring to us as like a copilot, or a sales assistant, or this thing that sits shotgun on calls to remind me to do the things I need to do while on a call. Everybody kept referring to us as a person. They try to give a person a name and not the lead person, but like the secondary person. It was Abbott and Costello. It’s actually really interesting.

When you become a client or start working with us, your URL that you log into is usually your company name and Costello. We want to be there as that copilot, or that sales assistant when you’re on calls.

Marylou: That’s great. I like when there’s levity involved in this whole thing. As you know, the prospector job could be pretty daunting and repetitive, and it could get to you after a while. Which is why, when you and I were talking offline, my latest rant is about the fact that I have been putting out this online class. I do a free one every year. The statistics remain constant in who signs up, who actually looks at the material, who does the homework, who attends the sessions, and it’s a sliding scale of less and less people as we […].

How do we resolve this? You’re a director of sales now, how have you been successful in getting these folks to put the time into mastering prospecting?

Phill: I think you hire for it. It’s easier said than done. I think in the interview, I think that’s type of topics that you have conversations about. A lot of times, what I’ll do with candidates, and it takes a little bit longer than the sales process, but I’ll throw something at them before we get on a call and see if they use it while we’re in the conversation.

I’ll say something like, “Hey, at the end of the call, can you just recap what we had a conversation about at the end? This is what the structure should look like.” I’ll see if they do it while they’re in an interview with me. Or I’ll say things like, “Hey you know what’s next? You’re gonna meet with Frank Dale, our CEO. But when you meet with him, can you do three points of research on him just to know a little bit about him and have talking points about him? I want you to ask this question specifically.” I’ll see if they do it naturally. If they do, typically that’s something that comes second nature to them. They just do it anyways.

I also ask questions around what’s in the book that’s you’re currently reading? What are you learning from those books? What’s the last book you read and what did you learn from that book? You could see if that person has a commitment to learning and self learning. I always laugh, if you can’t teach yourself something, there’s no way you’re ever going to let me teach you something. I always make sure they’re self learners in the interview process.

Marylou: I love that. I can relate to that and I told my students just the other day. I taught an MBA class, same material, these folks aren’t responsible for revenue yet. There is an executive MBA class but some of them are working as apprentices, or interns. They don’t necessarily have the need to generate revenue, or get commission, or payments. But, they had the gene of learning.

I had 18 students in the class, something like that. Everybody completed their homework. Everybody did their prospect persona definition, even if they didn’t have a real one, they invented one. They were so beefy and complete, I was amazed.

Then I have sales professionals who are responsible for revenue, who are responsible for making quota, not do the homework. I thought, okay, I take that personally because I think, “Alright. I’m a shitty teacher.” There might be some truth to that so I have to fail forward and make a lot of mistakes to become a really good teacher.

But of all the people who did do the homework, say there’s 20% of those people actually started using what they created in the homework. One of them, or two of them closed $300,000 deals. Some of my folks are all roles, but it just really supported, although not statistically relevant. It really supported the fact that if you do the work, and you consistently learn, you are going to get better, you are going to meet your goals, you are going to excel at this thing called prospecting.

Phill: Yeah, absolutely. It’s a role that when you dedicate time to do it well, it’s a differentiator, especially if you have phone skills. I always am interested in SDRs that are great “prospectors” but they don’t pick the phone up so a lot of their prospecting comes through emails. But then I’ve seen those types of people that usually follow their faith when it comes to I want to be an account executive, I want to start selling, I want to start talking to prospects. Some of these are just not putting together the skills that they need to have good, qualifying dialogue with prospects a little bit later down the funnel.

There’s something to spending some time in that seat and learning the role and being good at it. I think there’s different aspects that you really need to understand. I think you need to have, one, good conversational skills, I think that’s probably core. I think you need to be able to write really well. There’s even things like going to an english class, or going online and doing a quick class just to refresh you on basic grammar rules. Having your friends proofread emails and teach you why you’re doing it wrong, like going to people that’s having this stuff. That’s how you differentiate yourself. Learning about social media and following what it is you’re doing and and doing well, it does differentiate you.

I’ve never been a fan of what they call “social selling” where you’re actively trying to sell on social. But I think there’s something to building your brand over an 18 to 36 months process. It takes time to really build your brand out and build your network. It’s a time and seat type of thing where you have to learn certain amount of skills.

Once you learn how to master that top of the funnel, to your point, you taught a class in prospecting and it creates a $300,000 pipeline that closed for people. They have to learn how to open up deals that wouldn’t have existed before on their own. There’s just different tactics on how to do that.

Marylou: Right. I think you hit the nail on the head. There’s also different levers, there’s also different channels. I have a lot of clients whose prospectors are not used to the phone, they don’t like it. They say, “We can get our AWAF calls”—the are we a fit calls—“we can get those by doing text, by doing social, by doing email. We don’t need to know the phone.” But then when they get to the AWAF call call, or heaven forbid, a scoping call where they’re disqualifying and aligning their value proposition to what the buyer needs, or the buyer’s telling them how to create the plan for the next working session that they do together, that requires telephone skills, it requires studying psychology of the buyer.

It’s a very multifaceted role and top of funnel, 40% or 48% of people who were recently surveyed said prospecting is the hardest thing they have to do in the funnel. That may or may not be true but it’s a perception.

Phill: Right.

Marylou: Why not take the time? Have we not designated the roadmap properly, do you think, Phill? Because you’re saying this is what I do. Are you best practice, or are you Phill practice? Is this trial and error, or is this things that you’ve learned along the way that you’re actually benchmarking against other professionals like you?

Phill: Yeah. I have some benchmarks. A lot of these things that I’ve built over time just from managing so many different SDRs that have gone through these types of scenarios. But also, at the same time, I’ve made tens of thousands of cold calls in my life to get on the phone and learn how to qualify somebody out.

I think that sales is all about pattern recognition for the most part. If you can understand what happens next and what’s the common occurrence once you have something happen to you, really all businesses are pattern recognition. When you say something, there’s a certain response that typically goes back in response to make you understand, or help you understand. When you set a qualified meeting, there’s typically a next step that has to happen. It’s just understanding what’s the right next step that has to happen.

That’s what time and seat gets you. It gets you that pattern recognition to know I can do this again, I can do it again, and I can do it again. I really think why people think prospecting, they really think about what you just said, prospecting is the hardest part of the funnel, because fear just reaching out the unknown. I think that’s the hardest, that’s the gut wrenching point. Do they even want to have a conversation with me at this point? Cold calling is just really, really difficult because of that. Or even just pure prospecting because your percentage of being told no is much greater than most anywhere else in the sales funnel.

Marylou: You were saying that you have a process in place for hiring people. I don’t know if you can answer this. I’m curious more than anything else, because I know my percentages. When I go and work with clients that already have prospectors in place, we lose sometimes two out of three over the course of getting this thing up and running.

It could be a bad hiring decision, it could be they came in with one frame of mind and all of a sudden we’re turning them on their head by saying, “No, we’re doing it this way.” What is your success rate relative to the industry in hiring the right person and having them moving through that AE role, or maybe they say in marketing and do inbound leads? What percentage of people, when you bring them on board, hang out with you for longer than the 18 months, or 12 months, or whatever the life cycle is nowadays.

Phill: Yeah, absolutely. My number is always 18 months. I think that’s the right number for SDRs. I’ve done statistical analysis of the organization I’ve been at. Typically the 9-12 month mark is where you’re at mastery and you’re starting to figure out the role. As a master, you have to start doing the job very well and producing real pipeline that we can go close. For me, it’s thinking about from the 9 to 18 month mark is where we start to get payback off of a hire.

Let’s say early on in my career, it’s probably about a 50% success rate because I didn’t know what I looked for and I didn’t know as a manager what was my strengths from people that would report to me. That was probably my biggest gap. Over time now, it’s probably close to the 70% to 80% range, we’ll stay on at that length. But it takes time to understand what makes you successful or not.

Marylou: Do you actually go out to a recruiter to get people, or are you doing this hiring internally, or through your network? What do you find works better for you?

Phill: Yeah. I usually, internally will own it. I have a process to how I recruit, specifically SDRs. Like today, I run a local group peer for sales. I usually stay in contact with people that I meet that are SDRs. For me, I’m constantly, probably once every other week at least, I’m getting a coffee with an SDR that I either met in the past, or that is at a different organization I was recommended to speak to. I’m looking for A players. I want to know people that are performing well, because what I’ll start to see is characteristics of people that are in my local area that are high performing SDRs.

Typically when there’s an A player, they know other A players as well. Whenever I go to hire, I usually have a giant step forward because I’ll get a bunch of people that will make recommendations to come work for me. I build out a brand as somebody that’ll be good to work for. That does matter.

In my previous company when I open up a position, we had two roles open and I had 156 resumes in the first week for an SDR role. But it takes time to build out that network. I literally have a Google Sheet that has names of people that I’m meeting with. I set my quota basically every month to people I need to meet with.

Marylou: That’s great. Like always be closing, always be interviewing, and always be hiring, or what is your motto there? You spend a good portion of your time connecting with potential candidates, whether or not you have positions open, is that true?

Phill: Yeah, absolutely. I think there’s a lot that happens there. For me, it’s building up my network. Because I’m not the only person that runs a sales team here in Indianapolis, or even in the Midwest. I know people in Chicago, in Columbus, in Detroit, in Nashville that might also be looking for SDRs. I have a good friend in St. Louis that might be looking for SDRs.

Sometimes, it’s purely just me filtering SDRs to other people, building out my name and my network as well, and helping them find good quality candidates. That does matter. I do believe in the laws of reciprocity, that it will come back eventually. For me, it’s just building out my network, and knowing what a good A player looks like, and knowing what a hiring profile in my community looks like, and understanding what they care about as a candidate. That stuff does matter. Then you start to learn a lot more about the types of questions you should be asking the interview to relate to these types of people.

Marylou: That brings another question to mind. Once again, my students and my class, we have multiple buying scenarios. We have top of funnel, SDR business developers, some take it to the first meeting, some take it to a qualification, some actually develop almost to the point of a letter of intent. They find all the stakeholders, they make sure they’re serving up with the value prop so that once the AE becomes involved all the right people are sitting around the table, the virtual table in this case. How do you know which type of SDR goes to which role, or do you shop for the person who can get further into the funnel?

Phill: I typically like to hire someone less experienced.

Marylou: Okay.

Phil: And hire and train them. There’s different reasons behind that. I think some of it is you don’t have bad habits. I think their expectation for promotion is usually more aligned with what my expectations for promotions are. I think from a costing point, they’re typically more affordable when it comes to a candidate. I usually pay at market value anyways.

I don’t want to pay over market value for somebody that might produce a little bit more. I have never seen really a better result of having somebody that’s a lot more experienced. Most people that I hire, I don’t see a fit most times with people that want to be a career SDR person. That’s more my personal hiring profile. I just don’t align with them usually at my values and my management style.

For me, I’m very open and honest about what the timeline looks like for their promotion, but also trying to guide them and get them the skills along the way to be successful for their next role. It’s really understanding your own hiring profile, what works for you for a management perspective that does matter.

Marylou: That and how much time you’re able, willing to put in. Because the former model of getting a less experienced business developer in place means that product knowledge, even role playing, the conversations, there’s a lot more emphasis on the training aspect that the habitual role play, the understanding. You’re going to look maybe from a script right now but you’re going to memorize it like an actor would, so you sound natural.

Phill: Right. Exactly, 100%. When you think about where they go in the funnel and how far they go, I think there is some skill set things. You will get people that are SDRs that enjoy the role that will stay in the role. It doesn’t happen often but when you do, sometimes those people can take a little bit more.

There’s also things I’ve seen for micro promotions. Maybe your first six months you’re basically just finding out are they slightly past, do they have a pulse, and not quite to the place for it’s fully qualify. I have three or four […] to get you passed off. It’s like this person is alive and there is some kind of need and they have some kind of authority. That’s all I really care about from a very early perspective. They might stay that way even up to a year.

Once I get to that year mark, maybe that’s where you start to ask them to do a little bit more. Maybe that’s where you get into the play where they’re getting you. Are they aligned with budget, do they have any authority to sign, and I know for sure the signer is on the first call. I’ll even run maybe the first initial discovery, then I’ll hand it off to you. You give them additional tasks to help them build their tool trust to you guys over that time frame.

I’ve even created roles like Enterprise BDR roles where they’re essentially riding shotgun on large deals the whole time with the AE really helping almost the sales assistant capacity. Where they’re even going a little further in the funnel.

We could talk about them like a LOI type standpoint. Where it’s like this is something we definitely want to move forward with. Then they’re passing up to an AE, where the AE that works really more of like the MSA. There’s different ways I’ve seen of doing it. It just depends on what’s the best makeup for your organization and the size of the deal that you’re working.

Marylou: A lot of times I’ve seen, I was in this role when I first met Aaron way back in 2008. From Predictable Revenue, I was in the BDR role, business development role, where I served three account executives. Based on the account executive was how far I took it into the funnel. I had one that wanted a complete band, he just wanted to sit at the table and be an order taker. I had another one who could find money anywhere in the company. Even if there’s no budget, it was still a good opportunity for her to work.

I worked with the nuances of the account executives and called them in at appropriate points in the pipeline, but we mapped that whole thing out. That talk track was completely mapped out. It was mapped out by vertical even in some cases, some verticals converted faster. There’s a lot of nimbleness one needs if you’re going to be a corporate or an enterprise type sales business developer. But I see people in those roles for a longer period of time. They love dating, they don’t necessarily want to get married and get to the close.

I think it also depends on the corporate culture, where you are relative to the type of product you sell. In this case, that product was sold in three different ways. One is project based, fast and furious. The other one was like a medium size, where maybe one or two departments would want the thing because they were replacing old legacy equipment for example. The third one was a strategic initiative where it was a long term, required a lot of people, a lot of players. Depending on the way the product was sold, the band change. There was just a lot of those nuances that the business developer had to juggle and understand. Not that they can’t do it all, but it was a fun job because you never knew what was coming at you.

Phill: Yeah. I’ve seen quite a few career SDRs that are out there that do that and love it. I’ve had conversation with them because I’m just curious of why do you stay in this role? Obviously, you have the skill set to do something else, or do something different. Some of them even like team leads for the team and they just don’t want to do that anymore. They like the ability to come in, they make good money because they’re sourcing large deals, and they enjoy the role, they enjoy prospecting, and they enjoy the puzzle piece of how an enterprise organization works, or how a large mid market company works. They like that, they like the pace, they like the velocity, they like going home at 5:00 PM and having to be able to shut their computer and not to worry about it.

There’s a lot to that. I think it’s funny that the right mix, the right fit, and for that type of role, you have to find somebody that’s looking for a very specific type of job and type of role that has a very specific skill set. But there are also people that you’re probably not going to pay an entry level wage at the same time.

Marylou: Right. But like you said before, there are fundamentals that this role needs to have. It sounds like you’ve got a fabulous blueprint for uncovering the way they talk, the conversation canvas, what that looks like, how they have write. I’m a big stickler for writing, especially now that we’re all crazy about hyper personalization and stopping the credence to actually create and craft a one off email if you will, or template email that we are customizing.

But it’s a certain type of writing, it’s not like my daughter’s type of writing where she does thesis, and has a beginning, middle, end. This is persuasive copywriting. It’s fast, it’s emotional, it’s triggered, it’s not necessarily in the right order but it gets people to lean in. They have to have some knowledge of that. I love the fact that you’re making them do a writing assignment just to see where they are. Do they have the the quil, quiver behind their ear, that kind of writer, or they’re like a street writer.

Phill: Right. Either way, it’s fine. My templates are typically conversational. I believe prospecting should feel like, merely if you and I were shooting an email back and forth, actually for the last couple of weeks we shot emails back and forth to each other and they’re pretty conversational. They’re not just long drawn out like four and a half paragraph emails. I don’t know how you communicate as a person.

I try to teach them that type of skill. How do you write a conversational email that’s written like a salesperson to somebody that would be on the other end to receive that? It should be like an internal email, or an email they would get from a friend.

What I would say from an on onboarding perspective, as you started going out the path, I had a very, very clean documented process to how I onboard. The first 21 days, in fact, I know exactly what they’re doing that day in the first 21 days. Then after that, every week, I know what they’re doing what their goals are for that week. For me, I start at the very top. Just tell me  stories about how customers use the product. That’s all I care about.

We’ll start the first three days as really just tell me stories. Just remember every story possible. At the end of the day, you usually have to tell me two or three stories. At the end of the day they got to be able to say it without a piece of paper in front of them. Then by the end of the three days they have like nine different stories they can tell you about how customers used the product. The number one thing I used to hear from SDRs back before I used to do that from a process was I don’t know any customer stories, I don’t know how customers use it. I just forced that into the process and make it the first thing you learn.

Then we started, now we have a conversation. How do you open a dialogue, how do you have a conversation. Then I do an exercise, [00:25:30] out of New York where it is a day in the life of a prospect where basically you pick four to five businesses, or three to five businesses, and you make them learn how they make money, how they spend money, like what rules they have in terms of who you’re selling to, like how many layers of the organizations, who reads their company news, what are their priorities. You really learn about three to five business so they can start to recognize trends for the business. Then they read their profiles, or priority sheets for that role that you sell into. They start to really think about I’m trying to get my mind of the prospect.

Then I force them to demo a product to me. Day five or day six, you demo the product, you force yourself into getting really uncomfortable and show me the product which will get them some product knowledge, and then force them to really think about what that looks like. Then I teach them how to make questions on day seven. From there, day eight, you finished the day at day eight, you’re making at least 12 calls. It’s not a big number, it’s actually a very small number but I want to make 12 phone calls which is our number to get one conversation.

I basically want to get them in there and just see what happens. It’s usually enough to shake the nerves a little bit. In fact the last hiring class, one of the guys that we hired, the first time he picked the phone up, the first time he dialled, somebody answered the phone.

Marylou: Of course.

Phil: It’s funny, he called out our sales methodology, he’s like, “I’m working on it.” He’s like, “This the first day I’m calling.” He’s like, “In fact this is the first dial that I’ve ever made.” He opened up but he had enough stories to get the guy interested.

Marylou: That’s great. What a great story, I love it.

Phil: That’s my biggest recommendation. Get on the phone very quickly because it’ll shake the nerves really quickly.

Marylou: This has been great. I’m sure that sales managers, leaders listening to this phone call are like, “Oh my gosh, I would love to get my hands on some of what he’s doing.” How can people get a hold of you if they want to pick your brain, or have a conversation around your successes. What’s the best way to do that?

Phill: Add me on LinkedIn. I’m on that pretty frequently. It’s Phill with two Ls, Keene, or you can shoot me an email, it’s phill@ncostello.com. I’ll have you set up a call and I’ll walk you through my sales demo onboarding program, and how that looks, and what that looks like, and even share with you what mine looks like. We can go from there and have a good conversation. I’m happy to share all sorts of stuff that I have for resources.

Marylou: I appreciate that. I’ll also put all that into the show notes on your page. This will be transcribed. If there are bits and pieces you guys wanted to pick out of our conversation, we could probably put together a very simple little blueprint for you from the show notes. We’ll be happy to do that.

Thank you so much for your time. I think this has been a great eye opener for some of those sales leaders who are still beating their head against the wall as to how to hire the right person, and what that means, and what kind of knowledge they need to start up with, and how they can essentially grow into the role in some cases which is what you’ve had great success with. Having them grow into the role, sitting in that seat, learning more every day.

Thanks again, Phill.

Phill: Thank you.