Sales Pipeline Radio, Episode 348: Q & A with Phil Bokan



Matt interviews the best and brightest minds in sales and Marketing on Sales Pipeline Radio.

By Matt Heinz, President of Heinz Marketing

If you’re not already subscribed to Sales Pipeline Radio or listening live Thursdays at 11:30 am PT on LinkedIn (also on demand) you can find the transcription and recording here on the blog every Monday morning.  The show is less than 30 minutes, fast-paced and full of actionable advice, best practices and more for B2B sales and marketing professionals.

We cover a wide range of topics, with a focus on sales development and inside sales priorities. You can subscribe right at Sales Pipeline Radio and/or listen to full recordings of past shows everywhere you listen to podcasts! Spotify,  iTunesBlubrry, Google Play, iHeartRADIO, Stitcher and now on Amazon music.  You can even ask Siri, Alexa and Google or search on Audible!

This week’s show is entitled, Lessons from the SaaS Sales Trenches and my guest is Phil Bokan,

Tune in to learn:

  • The importance of personalized communication and the role of AI in sales.
  • Strategies for standing out and building relationships in a business landscape increasingly saturated by AI-generated messaging.
  • The importance of the enduring value of human to human sales interactions, particularly for complex purchases.
  • Matt & Phil’s predictions on baseball and the world series

Watch the video, listen in below and/or read the transcript below.

Matt: All right. Welcome everybody to another episode of Sales Pipeline Radio. I’m your host, Matt Heinz. Very excited to have you all here for another episode. It’s a week before Thanksgiving as we record this today, if you were watching and listening to us live, two things, one, I hope you have reserved your Turkey.

If you haven’t like there’s plenty out there. But if you were trying to reserve a farm raised, pasture raised Turkey, they’re probably all gone. You got a week, so get out there and take care of business. Also, if you’re watching live, on YouTube or LinkedIn, we’d love to make you part of the show.

If you have a question, if you have a comment, if you have a rebuttal, feel free to throw that in the comments. We will see that we can reference that we can throw those up on screen. And a feature you, and we would like nothing less. If you are listening to, or watching this show on demand, thank you very much for downloading for subscribing, for listening every episode of Sales Pipeline Radio past, present, future, always available to you on demand at www.SalesPipelineRadio.Com.

I’m really excited for this episode today. This might be one of the more unpredictable episodes. Phil Bokan, who I’ve known for a long time. If you’re in SaaS, you probably have bought something from Phil in the past, has sold for many of the more brand names in B2B SaaS and, excited to have him here with us.

We’re going to talk a little about advice from a sage, a successful, seller. I’m glad you got the beard. You got a little gray in it. You sort of playing the part.

Phil: You know, people listen to you more. And also on the topic of Thanksgiving, get your deals in before Thanksgiving people, you are going to sit, if you wait.

Matt: We are this close to “let’s circle back in January” territory.

Phil: Gets worse, right? Never wait, never put off for tomorrow. What you can do today.

Matt: Let’s get it right away. I remember someone told me once they said, especially if you’re getting towards the month or end of the quarter and you’re like, Oh, let’s just use this deal as a way to sort of kickstart the next month, next quarter. No book it. Now it’s better to be, it’s better to stare at a lower number. It’s going to motivate you. It’s going to keep the fire burning to get out and go do it again.

Phil: There’s no worse habit to get into than bringing a deal in on the second or third day of a month because your leadership will get mad at you about that constantly because it should have been in three or four days earlier. Absolutely.

Matt: Yeah, that’s right. Phil. For those that don’t know you or haven’t bought from you before, walk through where you’ve been and where you’re at now.

Phil: I have a long story history of SaaS , I started at Webex pre IPO. I was there at the tail end. I’m not old school Webex by any means, but I was there before Cisco bought us. I was paid in Cisco stock, not Webex stock. It’s still kind of a burning sensation. Anyway, I stayed in the Valley. I looked at tech as Hewlett Packard–it was, it was in the garage and I always kind of felt that the Silicon Valley was Hollywood when it came down to it.

So I up and moved to the Silicon Valley, good names like Marketo, Outreach, et cetera, always been earlier stage. Started doing research a few months ago. There’s so many like wrapper products and nice to haves. I cold called my current CEO, Trevor Rodrigues-Templar at Aviso Ai and we hit it off really well.

Great group of people; loving it. We’re doing really, well having a great time. I will say this. I’m in AI currently in forecasting. We’re a leader in the forecasting space. But what brought me here was…There’s no sentient being in AI right now. There’s just not. All trained, fixed, learned outcomes.

And really I’ve been in conversational intelligence before at the very front end. We’ve got a, how do I put it? A unique capability of sentiment analysis in both audio and written word. And since we deal with forecasting, I mean, you think about what that can add in terms of color and telling you how things really are.

So loving where I’m at. Trevor’s been featured in NASDAQ and New York Stock Exchange recently. So we’re pretty stoked.

Matt: That’s awesome. When we were talking the other day, you’re like, Hey, we can talk whatever you want. I’m just sitting here prospecting. You’re a senior guy who has sold large deals and after all the frothiness of all the ways that AI and intent signals are going to just hand deliver us deals, you’re still picking up the phone and calling and how many years later, that’s still part of your playbook.

Phil: Yeah, I’ve always said, and I said this to you many times, personalization at scale comes from your voice. We started getting into it back in the day in like 2011 and I shared with you about Twitter at first. It was like, they’re giving away all the plays. Like, everybody was giving away all their plays and it’s not about giving your plays away, but like, just telegraphing who they’re talking to. We get into the social sellers where they’re saying, I personally have never seen an order form come through LinkedIn.

Have you heard of any order form come through LinkedIn yet? No, no, never. It’s about building relationship and like getting in there right when it comes down to it. But I look at today and I look at the plagiarism machine that’s out there and when people are receiving the exact same formatted type of message and they’re just scrolling it, you have to do something different to stand out and I firmly believe that your voice is the way to do it.

You practice your pitch. I leave a message every single time I make a phone call and it resonates; they text the voice. It goes right to the day. It’s another hit for them, you know, so. Another thing, people aren’t leaving messages nowadays and that just blows my mind.

Matt: I wanted to cover that because some of the kids listening to this today may be, a little shocked that you’re actually using the phone and further doubled down on that shock when they said you actually spend time leaving a message? Explain to the people at home, you and I are on the thing on the same page on this, why that is still, so important?

Phil: You practice your pitch every single time. What are you going to do when you get somebody live, if you don’t leave messages? We’ve gotten into this aspect where the SDRs are like at all costs, get that meeting, right. When it comes down to it and it can’t be at all costs, get that meeting.

It has to be, there has to be some hooks in it. And the relationship really matters more than ever. Now, if you ask me, it really does.

Matt: Yeah, I’d agree with that. Talking today, with Phil Bokan. Talking today’s, lessons from the SaaS sales trenches. Say that five times fast.

Look, I come from a place where I think marketing has a responsibility to drive qualified, predictable pipeline to the sales organization. That is well meaning, but marketing is hard. Sales is hard. And at the end of the day, you can’t just sit and hope marketing helps you make your quota.

The best sellers I know are still fully in the trenches just doing what it takes. Talk to people that have never carried a bag. We’ve got we got sales professionals here. We got marketing professionals here. So a lot of people have not actually had to sell. We were joking the other day that sometimes people that are selling for the first time have to take some time to get used to the high volume of no’s, the high volume of doors being closed in your face and that you see the ring the bell notices and think, oh man, they just are closing deals. Talk about the carnage behind that if for people that don’t know how sales actually gets done.

Phil: I always make jokes that people see us at Morton’s after big deals close, we’re high fiving, but they never see us when we’re under our desk in the fetal position and nobody will call you back. Right? And its call reluctance is the one thing I think that everybody really faces at the end of the day. There’s always an excuse not to pick up the phone. Right? But it’s like, that is something that just has to be done on a constant. It’s muscle memory. it’s another channel. You reach people where they are.

I think the biggest problem we have right now is the percentages are all down of connect rate when it comes down to it. So you gotta be ready when you capture somebody and you have the time with them. Yesterday, I made 46 calls. I connected with two people. I left 44 messages, but one was a no and the other one stretched into a five-minute basic discovery call where I was led down the path and you have to be on, you have to be positive every single time. And that’s part of that, leaving that message, working on your tone also.

Matt: There’s a handful of sales influencers out there that still evangelize what you’re talking about. I think of the Jeb Blount, I think of the Anthony Iannarino’s. Jeb Blount, his tagline is just one more call, just to keep going. Talk a little more about call reluctance. Cause I think it’s fascinating to me that you talk to so many people in their profession, the things that they do are the things that they hate the most, you talk to some of the most famous writers, you know, and they will tell you about how much they hate writing. Like Ann Handley was the first person I’ve heard use the phrase, procrasti-baking.

She’s like, whenever I have to write, I have to first go bake a bunch of shit first so I don’t have to write. Call reluctance is real, even for the most successful rep. What causes that? Is it the fear of reaching someone live? The fear of actually performing when that happens? What drives that? And how do you mentally, combat that?

Phil: There’s always an excuse. Your mind, it’s busy work at the end of the day and it’s a grind. It’s not fun all the time, but it’s, it’s how things get done. Right? And you have to put on a suit of armor every day when you get here. You have to literally expect to hear “no”. The beatings will continue until morale improves. That’s basically dialing when it comes down to it. ? You catch somebody and you talk to them and a little bit of magic happens and the best time to keep going is right after that happens because you have that feeling. I mean, you know as well as I do, you can feel it through the phone when somebody’s having a bad day or they’re not approaching it correctly. it’s our best tool there is by far.

Matt: When you can get to the point where you actually get someone onto a video call, I know we don’t like staring at ourselves and it’s a very different function. We’re social animals that used to not know what we looked like at all.

Now, all of a sudden we stared each other for hours a day. You used to be able to walk into someone’s office and you can at the four walls and you get to know who they are. If you’re watching me, you’re like, okay, I think that’s a piano. I think that’s a typewriter. I think that’s a Husky helmet. You have some things you can reference. Like I could talk to you about baseball clearly from things behind you there.

Someone made a ketchup joke in a cold email to me the other day, so like they’re trying.

Just like I could say, Hey, is that actually Willy Mays signature on that thing behind you? That’s phenomenal. How and when can you use that as a way to either build rapport or just get someone’s attention?

Phil: So once you get a little hook, I think you’ve earned the right to be more personal, right?

I will not be disclosing what I do specifically, but I’ll build memes around specific use cases for the clients once I get to know them. And when I get that reaction, it’s everything right? I’m looking for a smile or a laugh when I do that.

But I’m not sending cold text. I’m not sending a cold anything off brand there. I want to make sure that I have a little engagement before I’m able to do that. And it’s all about using all your available tools to research and find out any nook and cranny. It’s not about like, Hey, the Pittsburgh Steelers, you know. My God, it’s the same case with intent data, right?

It’s like intent data will tell you what they’re doing. You think there’s a project or anything? No, it’s a game. You have to create within yourself that they’re a lead and you need to hit the right personas with the right message around whatever that is. And if it’s interesting to them, or there is a project there, they’ll talk to you.

So it’s about personalizing based on the person you’re talking to, the relevance, et cetera. I think that plays all the way out to when you get super personal and can make jokes and things like that, you know?

Matt: I think it’s also important when you note those things to literally write them down, like whether you’re in CRM or whether you’re using LinkedIn, like LinkedIn sales navigator has a place to put notes.

Salesforce does as well. Things like, what are they like, for instance, like I know you went to Oregon and Arizona. We’re not going to talk about Oregon. We just, the last thing we’re at last time, we’re going to use that name in this show. But you’re a wildcat. And I initially brought it up. I said like, Hey, cause I’m a college football fan. I’m like, Hey, your Wildcats are doing pretty well. You immediately pivoted to basketball. Right. And so, okay. Like I need to remember, like, if I want to engage you in just small talk moving forward, I should focus on basketball instead of football.

I’ve found over time, like sometimes if you’re not getting a response from someone that you want on the contract or like, Hey, what did you think of that proposal? That doesn’t work, but, Hey, how about that big win against Duke? You’ll get a response right away.

Phil: It’s all about finding out what’s important to them at the end of the day, and nothing that is important to me matters.

That’s the truth of it, right? Yeah, there’s a give and take, but I’m here literally at your service with my clients. That’s my job. You know, I want to make sure that I get them the right information. I want to make sure I’m giving them proper value in the conversations. It can’t be superfluous and brevity, I think is key in everything that we do as salespeople because there’s such an inundation in the land.

I mean, look at the notice that came out from the set players about how the rules are changing on Google. Well, that further emphasizes the fact that we have to personalize and the messages matter.

Matt: What that says too, is where people are worried about, isn’t that Google is not going to deliver your messages is that you have to have your spam alerts under a certain number.

So if you have relationships with people on your list, if they are expecting your email, if you have gotten to the point where your interaction is irresistible, not interruptive where they’re like, I love talking to Phil. It’s always fun. I always learn something new. You got nothing to worry about. If you’re skirting the rules, if you’re buying cold lists, if you’re sending bad emails, that finally is going to, I think, start to expire and it’s been gone in the media for a while and it’s coming here. For those that are doing good, authentic selling and marketing, you’re just gonna stand out that much more.

Phil: Yeah. You know, as well as I do, they can opt out, but if it’s a personalized actual message to them, there’s nothing wrong with sending it to them. And if you make it count, it counts and they might tell you, Hey, not interested wherever it is, but still playing within the rules and you’re doing what you’re supposed to do to get their attention.

Matt: A hundred percent, a hundred percent. People on this show probably heard me talking about this before, prospecting, even marketing, it’s like driving by someone’s house at 35 miles an hour, you’re trying to throw something in the mailbox. Most of its gonna miss, right?

Some of those voicemails are going to get deleted before they look at the transcript. That’s okay. You keep going. And if the next time they see something from you, it’s your name misspelled or a bad joke about condiments, is that really what’s going to get someone’s attention and compel the response you want?

We just have a few more minutes, Phil, before we wrap up here. Unfiltered, what do you need from marketing to be successful?

Phil: Air cover, and this goes back to John Miller when I was with him at Marketo. Marketing’s job is to make the eyebrow go up when we call.

So that’s all I want from them. If they do that and there’s information out there for people to self-shop, they do that, obviously that happens– I want to make sure that there’s information for them to research available out there. That’s all I ask. Get me in there coach.

Matt: Okay, I’m going to follow up and poke the bear. You don’t want leads.

Phil: Oh, I love leads. I love I will chase down anything that’s handed over to me. Absolutely. And you go to the person that it’s handed to you and then if there’s no response, you go around and you start asking questions about the inbound lead that came in, et cetera. So there’s no stopping. You just keep going until you get a response. I love leads. Don’t get me wrong.

Matt: I do too. I kind of expect you to go to the place that even a well-meaning marketing team is generating really crappy, unqualified leads and still taking credit for them and expecting me to do something with them and it doesn’t, it’s not always the case.

Phil: Hey, no, I love it. As I said, intent data. I love intent data because I treat it as if they are leads. And I look at it objectively about how the personas I’m going to go after. And it’s a great game for me to try to get business going. I love it.

Matt: I want to reiterate that for the people in the back that may not have heard that you don’t need a form filled out to have a lead. The fact that they actually fill the form out to get a white paper is an arbitrary signal. The fact that they actually have exhibited a real pain point or need in their organization is real and doesn’t matter what their behavior is to that point.

Phil: It’s your job to ask the questions around the value your product delivers. And if you ask those questions, you hit a nerve or you don’t, one of the two.

Matt: What are some marketing pet peeves?

Phil: Marketing pet peeves? I love my marketers. I believe that there’s marketing sales and alignment all the time and every organization. I’m teasing. I do love my marketers. They tried so hard. I know the effort they put forth. We meet on a regular basis. Every organization I’m with, I meet with my marketers to make sure that I’m giving them signals on what we’re seeing on the ground and that, and give them good feedback for getting good stuff back. Totally.

Matt: Yeah, yeah, exactly. The concept of sales enablement has been a big deal in the last couple of years. Sometimes that means technology. Sometimes that means process. Sometimes that means content. What are some of the best examples of sales enablement you’ve seen that have really helped you be a better seller?

Phil: Hands on has been the best that I’ve dealt with. There’s definite theory that goes on. A lot of it is not the rubber that hits the road. I think the best enablement comes from the operators that I know. I’m gonna drop some names here. Like you, for instance, I love listening to you. I’m not just saying that cause I’m here, but Corey Bray’s of the world, Craig Rosenfeld’s of the world. I learn things from people. Let’s face it. You go on LinkedIn, you have your, me twos, look at me, look at me, but the real operators are telling you how you should be behaving without giving you away the place and I take such value for that went from that, you know?

Matt: Yeah. Part of what I’m hearing you say is you’re sticking with fundamentals, like making the call, you know, that to be successful, you got to put in the work and keep grinding and I put your hard hat on on a regular basis.

And despite what you have learned over time, you’re continuing to [00:16:00] learn from those around you and saying, look, I think I’ve developed a set of knowledge that is converted into wisdom here that can help me sell.

How do you separate, of the new ideas and a new things you learn, new things you see, how do you try to separate out good ideas from the charlatans? Cause there’s a lot of snake oil out there. There can be snake oil marketed or sold by people that are very slick and very good at how they present themselves. How do you still separate the good from the crap?

Phil: We both have met a lot of the people that are involved in the social selling realm. And backdoor references is how I know people if I have not met them. I’m going to drop Corey one more time when I say this. My relationship with Corey Bray was based on the fact that I confronted him about something he said like four months before I saw him. I didn’t come from the peanut gallery and jump in on LinkedIn.

I wanted to talk to him about it. And we had a great conversation. We differed in opinion, but he earned my respect right on the spot because of the fact he had a valid opinion and was able to back it up on the discussion, right? And those are the type of people, you included, where you can have a good discussion about if it’s working, if it’s not, what’s the basis of this, what’s the value, why should I be doing it, et cetera.

And if there’s valid points, run right into the building and do it. Absolutely. Listen, I’ve been around a while. I’ve seen a lot of things. It’s like running. Everybody tells you what to do and you take what you can. But when you see people that have been successful, not just the look at me crowd on LinkedIn that are regurgitating things over and over again over the years. I mean, there’s some fresh ideas out of there. People that are real smart.

Matt: Last thing I would kind of go back to something you mentioned earlier, the increased use of AI and B2B sales and marketing channels. You said something about all these different companies are asking the same robot to write their emails, right? Some companies are starting to train their robots. Here’s how we want to sound. Here’s how we want to write and are getting unique stuff. But the majority are just going straight up and just saying, write me an email. So you end up with the same stuff.

Sometimes we say when robots sell the robots, I think there’s always going to be a human element. There are robots selling today. It’s called e-commerce, right? If you’re buying or selling something that is that simple and really is a commodity, then we’re not needed, but if it’s a complex sale, if it’s a complex decision, if there’s a lot of layers of understanding, the human to human element, I don’t see that going away anytime soon, and I think AI can assist in components of that. But I think to look someone in the eye and to shake their hand and to have confidence in the decision you’re making because of another person’s impact on helping you build that confidence– I don’t know. I have a hard time seeing that going away. When you’ve got these big considered purchases.

Phil: You have to be careful with the openness of this because it’ll steal your IP. That’s the problem, right? It’ll steal your IP and it goes into the big plagiarism machine. So the open aspect is terrifying to me.

And then how everything looks the same. It’s a pattern at the end of the day. You’re not going to stand out at all. And you have to be a pilot, not a passenger. Now you have to, because if you’re a passenger, you will be passed by. And it’s not so much about the convenience if you ask me. It isn’t about the convenience because you have to personalize what you’re doing.

I think that AI offers such an opportunity for organizational optics in real positive ways and guidance that we need to take advantage of it. Absolutely.

Matt: Two final questions for, before we let you go, who’s going to win the world series next year and why?

Phil: It will not be the San Francisco Giants because Farhan Zaidi needs to lose his job.

That’s one. That’s the only tea I’ve spilled.

Matt: This morning’s headline is that they’re going to sign Ohtani and trade for Trout.

Phil: They are not going to do anything. They keep saying it’s a waste. I would like the Texas Rangers of my new home state to win again, if possible. And what was the other question? Agnostic. I love baseball. I’m happy to see you.

Matt: The first question was who’s winning the world series and why, so you got Texas going back and back. And then related to Ohtani, like, where’s he going to land?

Phil: Dodgers. Most logical explanation is Dodgers. Money, West Coast, they have everything. I would love for him to go somewhere else. I think it’d be interesting.

Matt: He’s been mentioned with at least 15 teams now, right? And I think a lot of that’s wishful thinking on behalf of some of those teams that just aren’t going to be able to put up the cheddar to get them or get them to go to a location that is not probably what he wants either.

Phil: Half a billion dollars is if he’s pitching still. Half a million dollars is not if he’s pitching still so I think he takes a short term deal, maybe one or two years and then we see a big boy after that.

Matt: I saw a headline this morning that said, Hey, listen, if you’re going to sign Craig Counsell to 8 million a year, that’s just the start.

Go get Shohei. Get Shohei, re-sign Bellinger, I don’t know, trade for trout, just build a super team and see what happens. It could be fun. Anyway. Alright. Phil Bokan, thank you so much. Always a lot of fun to hang out with you. Thank you for your knowledge and wisdom. Thank you everyone for listening and watching.

We’ll not be here next week, next Thursday, it’s turkey time. Hot take Phil, I’m not doing turkey this year. I like to cook, I like to do meat, I like to smoke meat, I do rotisserie, I do spatchcock, I’ve done smoked turkey. Not doing a turkey. We’re gonna do we’re gonna do a ham. We’re gonna do a fresh ham not the spiral ham. We’re doing fresh ham to get the crackling. It’s gonna be phenomenal.

Phil: Barbecued turkey. Five and a half hours. Barbecue turkey indirect heat.

Matt: I’ve never fried a turkey and some people that just swear by the fried turkey.

Phil: You got to worry about grease fires. I mean, like water is involved with fire and grease. It’s a bad idea. Not in favor of the deep-fried turkey.

Matt: I’m not in favor of grease fires either. All right, well now we’ll let everybody go. We won’t be here next week. We will be here the last day of November, the week after. Thank you so much for joining us today, guys. Thanks again to Phil. We’ll see y’all next time. Take care.

Listen to the Latest Episodes:

Matt interviews the best and brightest minds in sales and Marketing.  If you would like to be a guest on Sales Pipeline Radio send an email to