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Lessons from the SaaS Sales Trenches · Sales Pipeline Radio

0:15
All right.
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Welcome everybody to another episode of Sales Pipeline Radio.
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I'm your host, Matt Heinz.
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Very excited to have you all here for another episode.
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It's a week before Thanksgiving as we record this today, if you were watching
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and listening to us live, two things, one, I hope you have reserved your Turkey.
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If you haven't like there's plenty out there.
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But if you were trying to reserve a farm raised, pasture raised
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Turkey, they're probably all gone.
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You got a week, so get out there and take care of business.
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Also, if you're watching live, on YouTube or LinkedIn, we'd love
0:46
to make you part of the show.
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If you have a question, if you have a comment, if you have a rebuttal, feel
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free to throw that in the comments.
0:52
We will see that we can reference that we can throw those up on screen.
0:55
And a feature you, and we would like nothing less.
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If you are listening to, or watching this show on demand, thank you very much for
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downloading for subscribing, for listening every episode of Sales Pipeline Radio
1:05
past, present, future, always available to you on demand at www.SalesPipelineRadio.
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Com.
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I'm really excited for this episode today.
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This might be one of the more unpredictable episodes.
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Phil Boken, who I've known for a long time.
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If you're in SaaS, you probably have bought something from Phil in
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the past, has sold for many of the more brand names in B2B SaaS and,
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excited to have them here with us.
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We're going to talk a little about advice from a sage, a successful, seller.
1:32
I'm glad you got the beard.
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You got a little gray in it.
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You sort of playing the part.
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You know, people listen to you more.
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And also on the topic of Thanksgiving, get your deals in before Thanksgiving
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people, you are going to sit, if you wait.
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We are this close to "let's circle back in January" territory.
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Gets worse, right?
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Never wait, never put off for tomorrow.
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What you can do today.
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Let's get it right away.
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I remember someone told me once they said, especially if you're getting
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towards the month or end of the quarter and you're like, Oh, let's
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just use this deal as a way to sort of kickstart the next month, next quarter.
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No book it.
2:01
Now it's better to be, it's better to stare at a lower number.
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It's going to motivate you.
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It's going to keep the fire burning to get out and go do it again.
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There's no worse habit to get into than bringing a deal in on the second
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or third day of a month because your leadership will get mad at you about
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that constantly because it should have been in three or four days earlier.
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Absolutely.
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Yeah, that's right
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Phil.
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For those that don't know you or haven't bought from you before, walk through
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where you've been and where you're at now.
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I have a long story history of SaaS , I started at Webex pre IPO,
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um, I was there at the tail end.
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I'm not old school Webex by any means, but I was there before Cisco bought us.
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I was paid in Cisco stock, not Webex stock.
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It's still kind of a burning sensation.
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Anyway, I stayed in the Valley.
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I looked at tech as Hewlett Packard, you know, it was, it was
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in the garage and I always kind of felt that the Silicon Valley was
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Hollywood when it came down to it.
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So I up and moved to the Silicon Valley, good names like Marketo, Outreach,
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et cetera, always been earlier stage.
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Started doing research a few months ago.
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There's so many like wrapper products and nice to haves.
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I cold called my current CEO, Trevor Rodriguez Templar, and
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we hit it off really well.
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Great group of people loving it.
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We're doing really well having a great time.
3:08
I will say this.
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I'm in AI currently in forecasting.
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We're a leader in the forecasting space.
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But what brought me here was.
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There's no sentient being in AI right now.
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There's just not all trained, fixed, learned outcomes.
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And really I've been in conversational intelligence before at the very front end.
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We've got a, how do I put it?
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A unique capability of sentiment analysis in both audio and written word.
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And since we deal with forecasting, I mean, you think about what that
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can add in terms of color and telling you how things really are.
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So loving where I'm at.
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Trevor's been featured in NASDAQ and New York Stock Exchange recently.
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So we're pretty stoked.
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That's awesome.
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When we were talking the other day, you're like, Hey, we can talk whatever you want.
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I'm just sitting here prospecting.
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You're a senior guy who has sold large deals and after all the frothiness of
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all the ways that AI and intent signals are going to just hand deliver us deals,
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you're still picking up the phone and calling and how many years later,
4:01
that's still part of your playbook.
4:03
Yeah, I've always said, and I said this to you many times, personalization
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at scale comes from your voice.
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We started getting into it back in the day in like 2011 and I shared
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with you about Twitter at first.
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It was like, they're giving away all the plays.
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Like, everybody was giving away all their plays and it's not about giving
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your plays away, but like, just telegraphing who they're talking to.
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We get into the social sellers where they're saying, I personally have never
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seen an order form come through LinkedIn.
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Have you heard of any order form come through linkedin yet?
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No, no, never.
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It's about building relationship and like getting in there
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right when it comes down to it.
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But I look at today and I look at the plagiarism machine that's out there
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and when people are receiving the exact same formatted type of message
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and they're just scrolling it, you have to do something different to
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stand out and I firmly believe that your voice is the way to do it.
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You practice your pitch.
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I leave a message every single time I make a phone call and it
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resonates, they text the voice.
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It goes right to the day.
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It's another hit for them, you know, so.
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Another thing, people aren't leaving messages nowadays
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and that just blows my mind.
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I wanted to cover that because some of the kids listening to this today may be,
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a little shocked that you're actually using the phone and further doubled
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down on that shock when they said you actually spend time leaving a message?
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Explain to the people at home, you and I are on the thing on the same page on
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this, why that is still, so important?
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You practice your pitch every single time.
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What are you going to do when you get somebody live,
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if you don't leave messages?
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We've gotten into this aspect where the SDRs are like at all
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costs, get that meeting, right.
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When it comes down to it and it can't be at all costs, get that meeting.
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It has to be, there has to be some hooks in it.
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And the relationship really matters more than ever.
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Now, if you ask me, it really does.
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Yeah, I'd agree with that.
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Talking today, with Phil Boken.
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Talking today's, lessons from the SaaS sales trenches.
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Say that five times fast.
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Look, I come from a place where I think marketing has a responsibility
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to drive qualified, predictable pipeline to the sales organization.
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That is well meaning, but marketing is hard.
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Sales is hard.
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And at the end of the day, you can't just sit and hope marketing
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helps you make your quota.
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The best sellers I know are still fully in the trenches just doing what it takes.
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Talk to people that have never carried a bag.
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We've got we got sales professionals here.
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We got marketing professionals here.
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So a lot of people have not actually had to sell.
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We were joking the other day that sometimes people that are selling for
6:14
the first time have to take some time to get used to the high volume of
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no's, the high volume of doors being closed in your face and that you see
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the ring the bell notices and think, oh man, they just are closing deals.
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Talk about the carnage behind that if for people that don't
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know how sales actually gets done.
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I always make jokes that people see us at Morton's after big deals close,
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we're high fiving, but they never see us when we're under our desk in the fetal
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position and nobody will call you back.
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Right?
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And it's call reluctance is the one thing I think that everybody
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really faces at the end of the day.
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There's always an excuse not to pick up the phone.
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Right?
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But it's like, that is something that just has to be done on a constant.
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It's muscle memory.
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it's another channel.
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You reach people where they are.
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I think the biggest problem we have right now is the percentages are all down of
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connect rate when it comes down to it.
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So you gotta be ready when you capture somebody and you have the time with them.
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Yesterday, I made 46 calls.
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I connected with two people.
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I left 44 messages, but one was a no and the other one stretched into a five
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minute basic discovery call where I was led down the path and you have to be on,
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you have to be positive every single time.
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And that's part of that, leaving that message, working on your tone also.
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There's a handful of sales influencers out there that still
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evangelize what you're talking about.
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I think of the Jeb Blount, I think of the Anthony Iannarino's.
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Jeb Blount, his tagline is just one more call, just to keep going.
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Talk a little more about call reluctance.
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Cause I think it's fascinating to me that you talk to so many people in their
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profession, the things that they do are the things that they hate the most,
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you talk to some of the most famous writers, you know, and they will tell
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you about how much they hate writing.
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Like Anne Handley was the first person I've heard use
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the phrase, procrasti-baking.
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She's like, whenever I have to write, I have to first go bake a bunch of
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shit first so I don't have to write.
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Call reluctance is real, even for the most successful rep.
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What causes that?
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Is it the fear of reaching someone live?
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The fear of actually performing when that happens?
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What drives that?
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And how do you mentally, combat that?
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There's always an excuse.
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Your mind, it's busy work at the end of the day and it's a grind.
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It's not fun all the time, but it's, it's how things get done.
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Right?
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And you have to put on a suit of armor every day when you get here.
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You have to literally expect to hear "no".
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The beatings will continue until morale improves.
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That's basically dialing when it comes down to it.
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? You catch somebody and you talk to them and a little bit of magic
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happens and the best time to keep going is right after that happens
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because you have that feeling.
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I mean, you know as well as I do, you can feel it through the phone
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when somebody's having a bad day or they're not approaching it correctly.
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it's our best tool there is by far.
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When you can get to the point where you actually get someone onto a video call, I
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know we don't like staring at ourselves and it's a very different function.
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We're social animals that used to not know what we looked like at all.
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Now, all of a sudden we stared each other for hours a day.
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You used to be able to walk into someone's office and you can at the four walls
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and you get to know who they are.
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If you're watching me, you're like, okay, I think that's a piano.
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I think that's a typewriter.
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I think that's a Husky helmet.
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You have some things you can reference.
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Like I could talk to you about baseball clearly from things behind you there.
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Someone made a ketchup joke in a cold email to me the other
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day, so like they're trying.
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Just like I could say, Hey, is that actually Willy Mays signature
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on that thing behind you?
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That's phenomenal.
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How and when can you use that as a way to either build rapport
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or just get someone's attention?
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So once you get a little hook, I think you've earned the right
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to be more personal, right?
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I will not disclosing what I do specifically, but I'll build memes
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around specific use cases for the clients once I get to know them.
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And when I get that reaction, it's everything right?
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I'm looking for a smile or a laugh when I do that.
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But I'm not sending cold text.
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I'm not sending a cold anything off off brand there.
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I want to make sure that I have a little engagement before I'm able to do that.
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And it's all about using all your available tools to research and
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find out any nook and cranny.
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It's not about like, Hey, the Pittsburgh Steelers, you know.
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My God, it's the same case with intent data, right?
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It's like intent data will tell you what they're doing.
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You think there's a project or anything?
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No, it's a game.
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You have to create within yourself that they're a lead and you need to
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hit the right personas with the right message around whatever that is.
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And if it's interesting to them, or there is a project there, they'll talk to you.
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So it's about personalizing based on the person you're talking
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to, the relevance, et cetera.
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I think that plays all the way out to when you get super personal and can make
10:16
jokes and things like that, you know?
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I think it's also important when you note those things to literally write them down,
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like whether you're in CRM or whether you're using LinkedIn, like LinkedIn
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sales navigator has a place to put notes.
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Salesforce does as well.
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Things like, what are they like, for instance, like I know you
10:30
went to Oregon and Arizona.
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We're not going to talk about Oregon.
10:33
We just, the last thing we're at last time, we're going to
10:34
use that name in this show.
10:36
But you're a wildcat.
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And I initially brought it up.
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I said like, Hey, cause I'm a college football fan.
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I'm like, Hey, your Wildcats are doing pretty well.
10:42
You immediately pivoted to basketball.
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Right.
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And so, okay.
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Like I need to remember, like, if I want to engage you in just small
10:48
talk moving forward, I should focus on basketball instead of football.
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I've found over time, like sometimes if you're not getting a response from someone
10:54
that you want on the contract or like, Hey, what did you think of that proposal?
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That doesn't work, but, Hey, how about that big win against Duke?
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You'll get a response right away.
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It's all about finding out what's important to them at the end
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of the day, and nothing that is important to me matters.
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That's the truth of it, right?
11:10
Yeah, there's a give and take, but I'm here literally at
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your service with my clients.
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That's my job.
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You know, I want to make sure that I get them the right information.
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I want to make sure I'm giving them proper value in the conversations.
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It can't be superfluous and brevity, I think is key in everything that
11:27
we do as salespeople because there's such an inundation in the land.
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I mean, look at the notice that came out from the set players about how
11:35
the rules are changing on Google.
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Well, that further emphasizes the fact that we have to personalize
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and the messages matter.
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What that says too, is where people are worried about, isn't that Google
11:45
is not going to deliver your messages is that you have to have your spam
11:48
alerts under a certain number.
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So if you have relationships with people on your list, if they are expecting
11:54
your email, if you have gotten to the point where your interaction is
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irresistible, not interruptive where they're like, I love talking to Phil.
12:01
It's always fun.
12:01
I always learn something new.
12:03
You got nothing to worry about.
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If you're skirting the rules, if you're buying cold lists, if you're sending bad
12:08
emails, that finally is going to, I think, start to expire and it's been gone in the
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media for a while and it's coming here.
12:15
For those that are doing good, authentic selling and marketing, you're
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just gonna stand out that much more.
12:21
Yeah.
12:21
You know, as well as I do, they can opt out, but if it's a personalized
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actual message to them, there's nothing wrong with sending it to them.
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And if you make it count, it counts and they might tell you, Hey, not interested
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wherever it is, but still playing within the rules and you're doing what you're
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supposed to do to get their attention.
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A hundred percent, a hundred percent.
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People on this show probably heard me talking about this before,
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prospecting, even marketing, it's like driving by someone's house
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at 35 miles an hour, you're trying to throw something in the mailbox.
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Most of it's gonna miss, right?
12:46
Some of those voicemails are going to get deleted before
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they look at the transcript.
12:48
That's okay.
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You keep going.
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And if the next time they see something from you, it's your name misspelled or a
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bad joke about condiments, is that really what's going to get someone's attention
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and compel the response you want?
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We just have a few more minutes, Phil, before we wrap up here.
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Unfiltered, what do you need from marketing to be successful?
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Eric did air cover , and this goes back to John Miller when
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I was with him at Marketo.
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Marketing's job is to make the eyebrow go up when we call.
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So that's all I want from them.
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If they do that and there's information out there for people to self shop, they
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do that, obviously that happens-- I want to make sure that there's information
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for them to research available out there.
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That's all I ask.
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Get me in there coach.
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Okay, I'm going to follow up and poke the bear.
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You don't want leads.
13:30
Oh, I love leads.
13:31
I love I will chase down anything that's handed over to me.
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Absolutely.
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And you go to the person that it's handed to you and then if there's
13:38
no response, you go around and you start asking questions about the
13:41
inbound lead that came in, et cetera.
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So there's no stopping.
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You just keep going until you get a response.
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I love leads.
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Don't get me wrong.
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I do too.
13:47
I kind of expect you to go to the place that even a well meaning marketing team
13:50
is generating really crappy, unqualified leads and still taking credit for them
13:54
and expecting me to do something with them and it doesn't, it's not always the case.
13:58
Hey, no, I love it.
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As I said, intent data.
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I love intent data because I treat it as if they are leads.
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And I look at it objectively about how the personas I'm going to go after.
14:07
And it's a great game for me to try to get business going.
14:09
I love it.
14:10
I want to reiterate that for the people in the back that may not
14:12
have heard that you don't need a form filled out to have a lead.
14:15
The fact that they actually fill the form out to get a white
14:18
paper is an arbitrary signal.
14:20
The fact that they actually have exhibited a real pain point or need in their
14:23
organization is real and doesn't matter what their behavior is to that point.
14:27
It's your job to ask the questions around the value your product delivers.
14:31
And if you ask those questions, you hit a nerve or you don't, one of the two.
14:34
What are some marketing pet peeves?
14:36
Marketing pet peeves?
14:37
I love my marketers.
14:38
I believe that there's marketing sales and alignment all the
14:41
time and every organization.
14:42
I'm teasing.
14:43
I do love my marketers.
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They tried so hard.
14:44
I know the effort they put forth.
14:46
We meet on a regular basis.
14:47
Every organization I'm with, I meet with my marketers to make sure that I'm giving
14:51
them signals on what we're seeing on the ground and that, and give them good
14:55
feedback for getting good stuff back.
14:56
Totally.
14:57
Yeah, yeah, exactly.
14:59
The concept of sales enablement has been a big deal in the last couple of years.
15:02
Sometimes that means technology.
15:04
Sometimes that means process.
15:05
Sometimes that means content.
15:06
What are some of the best examples of sales enablement you've seen that have
15:09
really helped you be a better seller?
15:11
Hands on has been the best that I've dealt with.
15:13
There's definite theory that goes on.
15:16
A lot of it is not the rubber that hits the road.
15:19
I think the best enablement comes from the operators that I know.
15:22
I'm gonna drop some names here.
15:23
Like you, for instance, I love listening to you.
15:25
I'm not just saying that cause I'm here, but Corey Bray's of the world,
15:28
Craig Rosenfeld's of the world.
15:30
I learn things from people.
15:32
Let's face it.
15:33
You go on LinkedIn, you have your, me twos, look at me, look at me, but the
15:37
real operators are telling you how you should be behaving without giving you
15:42
away the place and I take such value for that went from that, you know?
15:46
Yeah.
15:47
Part of what I'm hearing you say is you're sticking with fundamentals,
15:49
like making the call, you know, that to be successful, you got to put in
15:52
the work and keep grinding and I put your hard hat on on a regular basis.
15:56
And despite what you have learned over time, you're continuing to learn
16:00
from those around you and saying, look, I think I've developed a set
16:03
of knowledge that is converted into wisdom here that can help me sell.
16:06
How do you separate, of the new ideas and a new things you learn, new things
16:10
you see, how do you try to separate out good ideas from the charlatans?
16:14
Cause there's a lot of snake oil out there.
16:16
There can be snake oil marketed or sold by people that are very slick and very
16:20
good at how they present themselves.
16:21
How do you still separate the good from the crap?
16:24
We both have met a lot of the people that are involved in the social selling realm.
16:27
And backdoor references is how I know people if I have not met them.
16:31
I'm going to drop Corey one more time when I say this.
16:34
My relationship with Corey Bray was based on the fact that I confronted
16:37
him about something he said like four months before I saw him.
16:39
I didn't come from the peanut gallery and jump in on LinkedIn.
16:42
I wanted to talk to him about it.
16:43
And we had a great conversation.
16:45
We differed in opinion, but he earned my respect right on the spot because of the
16:48
fact he had a valid opinion and was able to back it up on the discussion, right?
16:52
And those are the type of people, you included, where you can have
16:56
a good discussion about if it's working, if it's not, what's the
16:58
basis of this, what's the value, why should I be doing it, et cetera.
17:01
And if there's valid points, run right into the building and do it.
17:05
Absolutely.
17:06
Listen, I've been around a while.
17:07
I've seen a lot of things.
17:08
It's like running.
17:08
Everybody tells you what to do and you take what you can.
17:11
But when you see people that have been successful, not just the look at me crowd
17:15
on LinkedIn that are regurgitating things over and over again over the years.
17:20
I mean, there's some fresh ideas out of there.
17:22
People that are real smart.
17:23
Last thing I would kind of go back to something you mentioned earlier,
17:25
the increased use of AI and B2B sales and marketing channels.
17:28
You said something about all these different companies are asking the same
17:32
robot to write their emails, right?
17:35
Some companies are starting to train their robots.
17:38
Here's how we want to sound.
17:39
Here's how we want to write and are getting unique stuff.
17:42
But the majority are just going straight up and just saying, write me an email.
17:46
So you end up with the same stuff.
17:48
Sometimes we say when robots sell the robots, I think there's always
17:50
going to be a human element.
17:51
There are robots selling today.
17:52
It's called e-commerce, right?
17:54
If you're buying or selling something that is that simple and really is
17:57
a commodity, then we're not needed, but if it's a complex sale, if it's
18:01
a complex decision, if there's a lot of layers of understanding, the human
18:06
to human element, I don't see that going away anytime soon, and I think
18:10
AI can assist in components of that.
18:13
But I think to look someone in the eye and to shake their hand and to have confidence
18:17
in the decision you're making because of another person's impact on helping you
18:21
build that confidence-- I don't know.
18:22
I have a hard time seeing that going away.
18:23
When you've got these big considered purchases.
18:26
You have to be careful with the openness of this because it'll steal your IP.
18:30
That's the problem, right?
18:32
It'll steal your IP and it goes into the big plagiarism machine.
18:35
So the open aspect is terrifying to me.
18:37
And then how everything looks the same.
18:39
It's a pattern at the end of the day.
18:41
You're not going to stand out at all.
18:43
And you have to be a pilot, not a passenger.
18:45
Now you have to, because if you're a passenger, you will be passed by.
18:50
And it's not so much about the convenience if you ask me.
18:52
It isn't about the convenience because you have to personalize what you're doing.
18:57
I think that AI offers such an opportunity for organizational optics
19:00
in real positive ways and guidance that we need to take advantage of it.
19:03
Absolutely.
19:05
Two final questions for, before we let you go, who's going to win the
19:07
world series next year and why?
19:09
It will not be the San Francisco Giants because Farhan
19:11
Zaidi needs to lose his job.
19:13
That's one.
19:13
That's the only tea I've spilled.
19:15
This morning's headline is that they're going to sign Ohtani and trade for Trout.
19:20
They are not going to do anything.
19:21
They keep saying it's a waste.
19:22
I would like the Texas Rangers of my new home state to win again, if possible.
19:26
And what was the other question?
19:27
Agnostic.
19:27
I love baseball.
19:28
I'm happy to see you.
19:29
The first question was who's winning the world series and why, so you
19:32
got Texas going back and back.
19:33
And then related to Ohtani, like, where's he going to land?
19:36
Dodgers.
19:37
Most logical explanation is Dodgers.
19:38
Money, West Coast, they have everything.
19:41
I would love for him to go somewhere else.
19:42
I think it'd be interesting.
19:44
He's been mentioned with at least 15 teams now, right?
19:47
And I think a lot of that's wishful thinking on behalf of some of those
19:50
teams that just aren't going to be able to put up the cheddar to get them
19:52
or get them to go to a location that is not probably what he wants either.
19:56
Half a billion dollars is if he's pitching still.
19:59
Half a million dollars is not if he's pitching still so I think he takes a
20:02
short term deal, maybe one or two years and then we see a big boy after that.
20:05
I saw a headline this morning that said, Hey, listen, if you're going
20:09
to sign Craig Counsell to 8 million a year, that's just the start.
20:13
Go get Shohei.
20:14
Get Shohei, re sign Bellinger, I don't know, trade for trout, just build
20:18
a super team and see what happens.
20:20
It could be fun.
20:21
Anyway.
20:21
Alright.
20:22
Phil Boken, thank you so much.
20:23
Always a lot of fun to hang out with you.
20:25
Thank you for your knowledge and wisdom.
20:26
Thank you everyone for listening and watching.
20:28
We'll not be here next week, next Thursday, it's turkey time.
20:32
Hot take Phil, I'm not doing turkey this year.
20:34
I like to cook, I like to do meat, I like to smoke meat, I do rotisserie, I
20:37
do spatchcock, I've done smoked turkey.
20:40
Not doing a turkey.
20:40
We're gonna do we're gonna do a ham.
20:42
We're gonna do a fresh ham not the spiral ham.
20:44
We're doing fresh ham to get the crackling.
20:46
It's gonna be phenomenal.
20:48
Barbecued turkey.
20:49
Five and a half hours.
20:50
Barbecue turkey indirect heat.
20:52
I've never fried a turkey and some people that just swear by the fried turkey.
20:56
You got to worry about grease fires.
20:58
I mean, like water is involved with fire and grease.
21:02
It's a bad idea.
21:03
Not in favor of the deep fried turkey.
21:06
I'm not in favor of grease fires either.
21:08
All right, well now we'll let everybody go.
21:10
We won't be here next week.
21:11
We will be here the last day of November, the week after.
21:13
Thank you so much for joining us today, guys.
21:15
Thanks again to Phil.
21:16
We'll see y'all next time.
21:17
Take care.