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Anthony Deighton of Tamr on Why Standup Comedians Are Great Marketers

On today’s episode of Scaleup Marketing I’m joined by Anthony Deighton, the Chief Product Officer at Tamr. Anthony has 20 years experience in enterprise software, including 10+ years at Qlik growing it from an unknown Swedish software company, to a public company and market leader.

Anthony and I talk about his experience building Qlik from the ground up, how product and product marketing teams need to work together, and what messaging development has in common with standup comedy.

[00:00:00] Tom Wentworth: [00:00:00] On today’s episode of ScaleUp Marketing, I’m joined by Anthony Deighton. The chief product officer at Tamr. Anthony has 20 years experience at enterprise software, including more than 10 years at click growing it from an unknown Swedish software company to a public company and market leader. Andy and I talked about his experience in building click from the ground up how product and product marketing teams need to work together.

And what messaging development has in common with standup comedy. Enjoy. Anthony. Thanks for joining me. How are you? 

Anthony Deighton: [00:00:32] I am well, and you 

Tom Wentworth: [00:00:34] I’m great. This is podcast number three. So you, you do not have to go through the learning experience. My other two guests have had to go through 

Anthony Deighton: [00:00:43] it’s much more efficient, that way, 

Tom Wentworth: [00:00:45] much more efficient.

So your background is, is really interesting. So just for the audience, just give us a quick, a quick what’s the. Your life story, 

Anthony Deighton: [00:00:57] my life story in 30 seconds or less. So, [00:01:00] began my career in tech at a company called Siebel systems in California. Worked there for six or seven years in the Valley during the.com boom, worked in enterprise software.

So it missed the boom, I guess, joined a small unknown Swedish software company called. Click as you call it, click tech at the time, moved to the East coast. Cause I figured out that working for a Swedish company from California was, a non-starter worked for click for a bit over 12 years. It took click from unknown Swedish software company to a high growth startup to public.

We took it public. We ran as a public company and then we took it private with private equity. so as I like to joke the full life cycle of an enterprise software company, Recently joined a company called Solonus, where I ran marketing. that’s a German software company that was moving to the U S so theme.

There is European companies coming to the U S and then a couple months ago, joined, as chief product officer at Tamer, which is a [00:02:00] Boston-based, software company focused on, data mastering. I should also say, You know, obviously do that. I also, been doing a couple of different boards. So out on the board of a geo analytics company called Carto, on the board of, Icelandic company, called grid, which is working to reinvent spreadsheets, and advising a couple of startups as well.

an interesting one out of MIT called unblock, which is looking at advanced analytics, as a space. So, you know, I try to keep my. Well, all involved, a lot of different things. 

Tom Wentworth: [00:02:32] Do you have time to do anything else or 

Anthony Deighton: [00:02:34] three kids and, you know, that, that also running, you know, homeschooling and, yeah, exactly.

Tom Wentworth: [00:02:41] So I work for recorded future and other Swedish company, our founder, Christopher Ahlberg founded. Spotfire one of your competitors, any comments on. Definitively what was better clicker Spotfire 

Anthony Deighton: [00:02:53] I won’t, I won’t take the bait, but what I will say is, There are some very important differences between [00:03:00] the two approach the Spotfire took and click took that that might be relevant.

you know, Spotfire took a highly verticalized approach. It was really deep in, in pharma and in, financial services and click took a highly horizontal approach. And, you know, you know, I think that may help explain the broader adoption of click. I also think click took a very global approach then, and Spotfire, it was pretty centered on trying to figure out how to be successful in the us.

You know, I think there’s a good argument to be made that the clinic has almost never figured out how to be successful. In the U S even to this day, especially relative to Tableau, but it was very successful. There was a market share leader in South Africa just to pick a random example. so yeah, it was some pretty big differences, but, yeah, 

Tom Wentworth: [00:03:45] congrats on not taking the bait.

That was a smart decision, but it is interesting, you know, Spotfire was very much the whole product, Jeffrey Moore let’s let’s really go deep in a vertical in their case, life sciences [00:04:00] and, and, No, they had a whole product solution for that. If you were in life sciences, building drugs, you use Spotfire.

Anthony Deighton: [00:04:05] Yeah. And, you know, click could almost never sell into those, pharma companies because, they were deeply embedded in using that product. And the product was very specific to, to the use case there. in fact, we, again, like we took a very opposite approach, click. From a product perspective was highly horizontal, not go to market.

The sales teams were organized vertically. We had vertical, specific messaging. we would go to market with different partners vertically, but the thing we shipped you, the product you actually were delivered was the same, regardless of the vertical. 

Tom Wentworth: [00:04:38] Might take, well, we can skip past this, but my take is that having a horizontal go-to-market earliest age works when you get to be a billion plus I, you know, the whole product makes a lot more sense, but, but you know, at that scale, I think a horizontal approach gives you a bigger market to go after which obviously for starters makes no sense.

[00:05:00] Anthony Deighton: [00:04:59] Sure. But I think from a, from a selling perspective, you need to speak the language of the customer. you need to think about who the right references are. you know, Tom Siebel used to say enterprise software as a reference selling business, by which means he means, you know, customers buy because their peers bought.

and so when you’re going to market, you need to be able to step into that account. And th you know, the, in a sense, the first and only question that they have in their mind is who else in my industry is using this thing. and so, you know, so there’s a strong incentive structure once you’ve closed.

The, the lead organization inside that protocol is to go to the find the other ones. I think, the distinction I would draw is in translating that into, okay, well, let’s actually go build a specific product for that, for that industry. I think then I would agree with you. Some amount of scale is necessary before you do that.

Tom Wentworth: [00:05:49] So let’s go talk about Siebel. So Siebel was where I think it was your first sort of job in tech way back in the day. I don’t think enough marketers study the all time [00:06:00] greats and I put Tom Siebel in the all-time greats category. Tom Siebel grew up under, you know, under, before Benioff grew up under Larry Ellison, right.

Who was one of the greatest ever do it? I think a lot of marketers could learn lessons. You know, we study. The current, you know, there’s a lot of current thought leaders, we all admire, but like we got to go back. What was it like to work for Tom Siebel and Siebel back in the day? 

Anthony Deighton: [00:06:26] Sure. So first thing I’d say is, you know, Tom is one of the greats, but there was also a great, team there.

Pat house, was his co-founder, was a phenomenal marketer. And I think, especially from a marketing perspective, Was probably the primary driver of creating awareness and demand behind, behind click, or either behind, behind seatbelt. There are also people like Dave Schmaier who went on to found velocity, which was recently acquired by Salesforce, who ran product there.

you know, a great, kind of at Ebos at C3 now, which is Tom’s [00:07:00] latest company. So there was a pretty, you know, remarkable, senior executive team, there, and, So, I mean, there’s a whole bunch of lessons that I’ve taken and I use frankly to this day, from Siebel and sometimes they’re kind of anti-lessons, they’re things that worked well in the early days of enterprise software that I think we are lessons we should unlearn, today, but I think it would be fair to say that, Siebel systems and Tom Siebel sort of invented the big deal.

strategic enterprise software sales strategy and a sales driven culture and company. and, you know, that reason it took, you know, became, came into its own under, under Tom’s leadership. one of the sort of early lessons that I learned there, it’s something that I, I use to this day. is, is both thinking big and asking for what you actually want, you know, very, you know, Siebel in the early days, you know, wasn’t an enormous company.

It was, it was still very much a startup. [00:08:00] Even when I joined and I joined, it was probably about 700 employees, but it still had very much, the feeling of a startup grew to be about 8,000, so 700 to 8,000 while I was there. you know, but it never acted like a startup. Even as a true raw startup, you know, Tom would walk into deals into negotiations with partners, into, you know, closing a deal and act like, the market leader, and act like, you know, someone who, and, and not him personally, but he would have the whole company act that way.

And a good example of this is, you know, you want to go do some, we, we did a, a big deal, at Segal kind of co-marketing relationship. And, without divulging any secrets, the team met with Pat house and Tom’s okay. We’re going to go into this negotiation with IBM around this co-marketing event or co-marketing program.

You know, what should we ask for? And the team’s like, well, you should ask for X. And Tom said, no, no, no, no, no. We’re going to ask for 10 X and I’m talking here about, you know, tens of millions of dollars. And it seems like there’s no way that we [00:09:00] can’t ask IBM we’re Siebel. Like, and he’s like, Nope. And you know what?

They closed at the co-marketing for five bucks. So, you know, so they had a five X, you can call it a five X return on bravado, meaning like by asking for what they wanted or more than they wanted, they anchored in this case, the co-marketing partner. and, and ultimately did, you know, an enormous co-marketing program with IBM, you know, so it’s a good.

Thing to remember, especially as a startup, you know, you know, you asked for what you want and think about, you know, what your real desires are. And then, you know, it’s almost like multiplied by 10 and then if you ended up back from that still a great outcome. 

Tom Wentworth: [00:09:43] It’s interesting. I think that there’s a lot, there’s a lot of the enterprise selling DNA that came through Siebel that came through Oracle that came through PTC.

You know, we train a generation of account execs to go do what you [00:10:00] just said. Right? They didn’t have access to fancy tools. They just had swagger and confidence in a nice suit. And I think a little bit it’s good that, that, that DNA’s getting lost right now. The new enterprise account reps all come out through inside selling it’s a different skill set and mindset in a lot of cases.

And I worry that we’re going to lose a lot of that DNA in this new world. Right. I don’t know that, that in the new selling models that we see that you see the same sort of skill sets anymore. 

Anthony Deighton: [00:10:34] Yeah, I agree. And I, even if you’re selling, high velocity sales cycles, you know, I mean, obviously everyone’s almost selling over the phone these days, you know, it’s a question of, again, like.

Holding to your guns, asking for what you want, having confidence in your offering and the you as a company. you know, those, those things are don’t change based on the price point. and, you know, it’s also about setting ambitious goals. So as a [00:11:00] marketing team, you know, you’re, you’re going to put on a virtual event, you know, set, an aggressive target for what you want to do.

For attendance or for concurrent viewing or whatever the metric that you care about is, or how much pipeline you want to generate. you know, when you set ambitious targets, people have a tendency to, back solve into how they achieve those. when you, engage a customer. And, and ask for a high price point or reject the, the request for a bigger discount.

You know, you know, you want what, every one of those, but if you win half of them, it’s it’s energy well-spent 

Tom Wentworth: [00:11:34] yeah, we had, you know, we’re, we’re transitioning to the OKR process here at recorded future. And we’re just getting our arms around how to set goals. And, and we recently brought in Rick cloud from formerly of Google and Google ventures, who really was, was one of the big OKR advocates at Google.

And he spoke to us yesterday and talked about goal setting and they found very, it [00:12:00] was interesting, you know, they would set massively ambitious goals, not like. We’re going to make something increment 20% better, but we’re going to get a billion, Chrome downloads. And they, as they did analysis of that, they uncovered that the achievement rate for, you know, for incremental goals versus stretch goals was basically the same.

But people just, it takes a mindset change to set ambitious goals because people don’t, people are afraid of failing. And that’s why they’re like, I’d rather beat an incremental goal. Then miss an enormous goal. And I’m like, actually, no, you don’t want to do that so 

Anthony Deighton: [00:12:35] well, they perceive that the incremental goal is easier, but actually the incremental goal is as you point out the achievement rates the same.

So the incremental goal is. Equally, achievable. And I, frankly, if I look back over my career at all of the fun and the things I’m sort of most proud of and excited about and look at, you know, these were things which when we said them out loud, we said, that’s bananas. Like there’s no way, well, what if, you know, [00:13:00] what if we did that, what would we need to do?

And what could you straight would we need to lift? And, you know, what person would we need to convince or whatever, you know? And. Once you start thinking that way, you know, if, you know, if I’ve been a part of a hundred of those, maybe we’ve only achieved 50 of them or, you know, like, you know, but I can tell you those things 50.

I remember, you know, like, yeah. I don’t remember the fails as it were. 

Tom Wentworth: [00:13:22] But that’s the, maybe that’s the lesson is if, if you set an, whether you’re using whatever goal framework, doesn’t matter if your initial reaction is this goal is not bananas, you’re probably not thinking aggressively enough about it, right?

Anthony Deighton: [00:13:36] Yup. A hundred percent agreement. So, yes. I think almost every goal setting exercise should have a sense of discomfort, about it. 

Tom Wentworth: [00:13:46] yeah. So then you leave Siebel. was this point Siebel’s still independent or they’d been acquired by Oracle yet? 

Anthony Deighton: [00:13:54] Yeah, so I left probably a year, a little less than a year before they were acquired by Oracle and I, I left [00:14:00] quite honestly because of that.

So it had to become clear to me in working their day to day that they were looking for a way to exit the company. And so it was no longer. You know, in a place that sort of was leaning forward and, and, and try and do new things. It was trying to, you know, keep treading water until it could figure out a way and an exit strata.

Tom Wentworth: [00:14:21] Yeah. A little old company called Salesforce. also might’ve had something to do with that too 

Anthony Deighton: [00:14:25] big time. And there were a ton of, ex CBO people that went to Salesforce and were incredibly successful, there. So, yeah, and I, and I think there’s a good, there’s a good lesson in. disruption. I mean, it’s something that I, studied, you know, in, in the MBA program, you know, like disruptive technology and how, industries are remade and Siebel.

Salesforce is a perfect example of that disruptive disruption, upending, a market leader. 

Tom Wentworth: [00:14:56] So you went from you go to see a Siebel to this little tiny company called [00:15:00] click the Swedish company. We talked about it. What’s most interesting for me about your journey at click and maybe your career arc all together is that you’ve bounced back between product, product marketing and CMO roles in various, various times in your career journey.

And I want to probe a little bit on, on what you’ve learned in doing that, but it click, I think your journey was, I don’t know the exact order, but you know, product manager, product marketer, ultimately to CTO, like what was the order of that and how did that journey happen? 

Anthony Deighton: [00:15:33] Yeah. So when I joined click, I was actually VP of marketing, and you know, the, the logic was that I wasn’t a developer, and I wasn’t a salesperson.

So that meant I have to be a marketing, like by process of elimination. you were in marketing if you weren’t a sales person or development. and, and then over time, I naturally gravitate gravitated more towards what I would call product marketing. and then, [00:16:00] the, the CTO of click, who, and in Europe CTO as a bit of a different meaning than it does in the U S but in Europe, a CTO is somebody who runs the development team effectively.

so he was, he was injured in a horse riding accident. So he had to leave the business. He’s he’s okay now, but, so he hit the sort of a sudden departure. So I took over the development team and therefore also took over the CTO title. and it was also right at a very critical time around building sort of re-inventing click and building click sense.

and, and then, you know, I kept that title. I think it would have been fair to say that in the last couple of years that I was act like I was probably closer to a chief product officer than I was to the chief technology officer. Quite honestly, I just never bothered sort of updating the title. So it was good.

but yeah, so, but the arc is right and, and that also relation between marketing product marketing and, product management. And even to some extent engineering management, which again I did for a [00:17:00] little while as well. I think of that as a, as a continuum. I should also say that at Siebel, we did not make a differentiation between product managers and product marketers.

There was no, everyone was a product manager to be. The title, and, you know, that there was no, separate role. and, and the people who were most successful at C able we’re the ones who could figure out a way to both have a conversation with the customer, and support a sales cycle, and then turn around and have a conversation with an engineer and drive a release.

You know, like the same human being could do 

Tom Wentworth: [00:17:35] both. So that’s. Unusual, you know, I think obviously now the model is, you know, product marketing sort of owns more of the go-to-market side of it. And product management often owns more of the. The backlog and the prioritization for better or worse, but, but what’s the, what should it show, does that make [00:18:00] sense, right?

Should we be thinking about, I guess maybe I’d love to understand your now that you’ve been in so many sides of this, how do you delineate between what a product marketer does and what a product marketer should do? 

Anthony Deighton: [00:18:11] Yeah, so, so first of all, I will say that I, I do have a, a bias, which is, I don’t think we should make a strong, a differentiation.

As we do. So, meaning I think this, Organizations which create very strong boundaries between product managers and product marketers. they lose something in that. and while I agree with you that it’s hard to find people who can bridge both. I think just because it’s hard doesn’t mean we shouldn’t do it.

I think you should look for people who can do both. that said, I think that there are different tasks at play here. you know, primarily I see, the product marketer as the person who’s. translating, what we’ve built from a product perspective into language that the customer cares about that they’re, that they’re, they can understand, or they want to engage in and that they effectively want to buy.

[00:19:00] And that the product manager is responsible for translating the needs and requirements, of the customer into something that an engineer can understand that they can then build. and, you know, those are, I think of those two things as two halves of a coin. you know, so, the perfect sort of, is the, a microcosm of it is you show up at a customer site, you pitch your product.

So you’re sharing the product marketing messaging, and positioning for your product. And you know what you’d like the customer to eventually buy. And, and the customer buys it and then they give you feedback as they’re deploying it, which you then bring into your engineering team. Like, like that, to me, that cycle is sort of what I would love to see more of versus this kind of like a process where we sort of throw two different people at that task.

Tom Wentworth: [00:19:50] Yeah, it’s interesting. You know, I’ve, I’ve never been, not true. I was a product manager for a couple of weeks, a couple of weeks, once it’s a [00:20:00] long story. I ejected from a company after getting an, it was not good. I don’t want to get into it here. And on the record, like back in 2000, when I lived in foster city, it’s a matter of fact, But I have been a product manager for brief time, but I have been a product manager for a long, our product marketer for a long time.

And one of the things that, that I, I think is been a blessing and a curse to product marketers is the advent of tools like gong. Right? So gong is this unbelievable. Platform that records every customer call and, and analyzes, you know, creates text transcription and puts in. It looks for specific words and phrases.

But what I always liked as a product marketer was getting out in front of customers, myself, and doing a pitch and gong doesn’t solve that problem. How, how do you think, like what’s the best way if you’re a product marketer and you’re, you’ve, you’ve broken it up the way you’ve described, right. What’s the best way.

Do you think gong is enough to be able to be a good product marketer? 

Anthony Deighton: [00:20:58] Absolutely not. I think gong [00:21:00] is one half of the equation. it’s a wonderful tool, for example, to understand. Can your Salesforce articulate your message? Right. And also to some extent, Can the recipient of that message. You know, what questions are they asking?

Can they, can they understand it? it’s a great tool for that, but it is absolutely no substitute for standing up in front of the customer, you know, virtually or in real life and doing your pitch. one of the things we were talking about Siebold, Dave Schmaier, who, who, who ran product there, you know, I for a bunch of random reasons, I was kind of worked closely with him, over the course of a bunch of times.

So I would watch him do the Siebel pitch. And the thing I noticed about it is he always said the same thing every single time, same jokes, same pauses. Like it was like, you literally wind him up and hit play, and then out it would come in. Now it was 95% the same every time. And it was 5% that was different.

And what you could see, what he was doing [00:22:00] was he had his pitch. And he would see what worked and then he would tweak and he would change 5%. And so each time. Tweaked by 5%. and then, you know, over the course of, you know, a month or two, that the pitch would shift so to speak, you know, you’d see different things being emphasized, et cetera, that sort of rigor, is something that I think is really important.

And there’s a tendency I see for, for product marketers today, they almost take a kind of like textbook a theoretical perspective to building, building a pitch. and you know, they’ll, you know, they’ll write some great PowerPoint. And then you’re like, well, how many times have you delivered this? Like how many times you’ve done it in front of an audience to see what they go for?

and the answer is like zero or one, or I did it for my cat or, you know, no, like. Take it on the road. Go see, go see it. But by the way, I’ve always thought that for me, that work is very close to what it means to be a standup comics. So stand up comics, the way they, you see these one-hour Netflix specials, the [00:23:00] Netflix special, like literally the person could be asleep and do that special.

Like this zero new material there. What they’ve done is they’ve spent the last year and a half traveling clubs, these tiny little clubs and trying material and having a bomb and having it not work and then doing it again and then tweaking it and putting the emphasis here and trying a different punchline.

That’s the same thing. We do a great pitch comes from that. Like it, when you do it well, you’re completely bored by it. Like, it’s like, I’ve done this 32 times this week and I’m just sick and tired of it. that’s when you know, you’re starting to get good. 

Tom Wentworth: [00:23:36] it’s I got three pieces of feedback there. One, I now have the title of this podcast, something about, you know, stand up comedy and product market day.

Number two. I want to be, my dream job would be to be a standup comedian someday. So maybe after, you know, when I’m in my sixties, I don’t know if it’s too late or not. I’ll be at the comedy store in 

Anthony Deighton: [00:23:56] LA 

Tom Wentworth: [00:23:58] working on pitches, but [00:24:00] I came to part of, so my path was I came to. You know, graduated you and I are. And also this is a weird coincidence.

First three guests I’ve had on my podcast were all math majors. I was a math major as well. We’re all former CMOs or CMOs students seems weird to me. None of us went to school for marketing yet. Here we are. 

Anthony Deighton: [00:24:18] well, but the funniest people in the room are always the mathematicians. 

Tom Wentworth: [00:24:21] Yeah, exactly. That’s a lie.

Differential equations are hilarious. and then I came in through an se, so I graduated the CS degree, and, and got to be an se. And I would always have product marketers asking, you know, asking me to go out and pitch pitch customers. And, you know, they they’d come along and hear me do the pitch and like, Oh, you’re pretty good at this.

Maybe we should bring you over to product marketing, but I had some product marketers were fantastic. I would work with and I would use their stuff verbatim. And I always had respect for those product marketers, but then I’d have product marketers would give me stuff that I would tear out 80% of it because it just didn’t work.

And these were product marketers that the field, I [00:25:00] always felt like the simple way to look at how successful something is, is if the field is pulling you in, like your S your pitch is so good, they want to hear you deliver it. And if that isn’t happening, That’s that that’s a sign of something. 

Anthony Deighton: [00:25:13] Exactly. So if, if you’re a, it, if you embark on this standup comedy career, which I have, and when you embark on your Stanford, you know, if the clubs won’t book you, that’s good feedback.

Like that’s just the Navy, your, your, stuff’s not that funny. and, and, and you’re a hundred percent, right? Like if, if you’re a product marketer and you’ve built a pitch and no one’s interested, if it’s not compelling, It’s not the right pitch. It may, if it may check all the boxes, it may be the perfect, you know, sort of.

Structure, but it’s not resonating. and, and there’s no substitute for the answer to that problem is not, you know, to go back into a dark room and rebuild your pitch. The answer to that is, you know, go book another club, meaning like go find someone to do that pitch for that, that you might reasonably be interested [00:26:00] in your product and then do it again and then do it again and then tweak it 5% and then tweak it 5%.

And it’s that, that repetition that gets you to a place where bye-bye. A subtle sort of, allegory or, or, parallel to here. We do these big events. you guys just put on your big user conference, super successful, you know, Tamar did the same thing. We do these big events and the feeling is that what we need to do for those events is build a whole new pitch, right?

We want all new decks, all new PowerPoint. It’s going to be great. It’s always a disaster. 

Tom Wentworth: [00:26:30] Yes. 

Anthony Deighton: [00:26:31] The better thing to do is to take the thing that really works. Sure. You know, clean it up, tune it up, you know, and then in the month before, you know, let’s say it’s either it’s you or you’re a CEO. That’s doing the pitch in the month before do that pitch every single day.

And not to yourself, I go find a customer like by the time you do it, On stage for the, for the audience, you should be so thoroughly bored by it. Then, then you can do it in your sleep. and it be [00:27:00] great. Like the audience will love it because while you’re bored with it, you know, you will have, you’ll hit your marks.

Your timing will be good. Your, you know, the, the, the points that resonate will get emphasized, the things that doesn’t are cut, like it’s, it’s tight. It’s. Crisp. Yeah, it’s it’s a really, you know, if, if your, if your, if, if when you get on stage, at a big event, virtual or not, if that’s the first time you’re doing that PowerPoint, it’s going to fail.

If it’s the first time your CEO seen it, it’s going to fail. But if it’s the 80th time, it’s going to be really great. 

Tom Wentworth: [00:27:31] Yeah, we got lucky. So we just did our presentation, our predict event about a month ago, but we we’ve focused mostly on messaging that we had developed for a launch over the whole summer.

So by the time it predict came around, this was stuff that had been practiced over and over and over again. But it’s good feedback going forward. I think as marketers and I talked about this in my last episode there. Sure. We, we, we like to move on too quickly from things. And my saying is by the time marketing is bored of something, [00:28:00] sales is just starting to get it by the time sales is bored of something.

Customers are just starting to get it by the time customers get bored of something is when it’s starting to work. And you should maybe in a few years think about something new. 

Anthony Deighton: [00:28:10] I think that’s very Sage advice and, and, very consistent, you know, with what I’ve seen. Yes, I think that’s, there’s You know, in some cases the mood, the best thing to do.

And frankly, the hardest thing to do as a marketer is to be consistent. There’s a tendency to want to do new things and try new things, you know, repetition, and, consistency. This is true by the way, in, you know, your product messaging. It’s probably double triply true. When it comes to things like branding.

and that like, I always laugh at these companies that sort of, you know, flip around and change their brand and stuff every, every year. you know, the, the, the consistency and, and in fact, one of the things I think helped make a click successful in the early days, is [00:29:00] the product has this metaphor in the actual product of green, white, gray.

Green is selected. White is included. Gray is excluded anyway. All of the branding we did was green, white, and gray. we also have this early problem and decision we needed to take, which is, you may have noticed with click, we spelled the company. Q L I K there’s. No, you, it’s. Nobody could spell it.

It was a complete disaster as like a brand name. So we needed to sort of solve the problem. And we took a decision, which was a, we called it leaning into the queue. So everything became about the queue. Like we lean into this thing, which was a, it was a challenge. And then we just kept at it. And so even to this day, you know, click is green, white, and gray, and it’s got the cue and it’s, it’s all about that.

It’s, it is a very powerful, a very powerful 

Tom Wentworth: [00:29:47] technique. Done over years, decades and centuries, not done over quarters, which is course like we do is we do it as marketers. 

Anthony Deighton: [00:29:55] Yeah. And again, like, I should be really careful here. That doesn’t mean you never [00:30:00] change anything. What am I, you know, like I think go back to the, the Dave Schmaier example, you know, it’s.

You want to change 5% on every iteration you’re, you’re tweaking you’re you’re you’re tuning. you’re you’re buffing the edges. You’re finding the, the sharp points and taking them off. you know, that is the, that’s the trick. And what you’ll find is that over a period of time, a year or two, a lot will change, but it will not change 180 degrees.

It will, it will become. Sharper tuned, edited, focused, powerful, effective as opposed to different. 

Tom Wentworth: [00:30:39] Yeah. And I think that the only way that lasts to close us off dealing with that last mile tuning works is doing it in front of customers, not doing it, you know, in front of your cat or in a zoom.

But that last 5% can only be done out in the front lines. 

Anthony Deighton: [00:30:54] Yeah. No, a hundred percent. You need to, you need to literally read the room. Like, what are people reacting [00:31:00] to, you know, again, like, you know, like running your material in the comedy cellar in New York, like that’s the way you find out. And, you know, standup is, is much more, visceral and direct in the sense that you will literally get heckled and yelled at and stuff thrown at you and you won’t get booked together.

Like it’s, it’s a very direct point of feedback. but you know what? Enterprise software customers do. Very similar things. 

Tom Wentworth: [00:31:23] I was an se for a long time, man. I used to get some, maybe not things thrown at me, but I’ve had people get up and walk out before a, of a demo that didn’t feel good. 

Anthony Deighton: [00:31:33] Yeah. Again, like, and you know, it feels bad in the moment, but it’s actually, It’s great feedback.

Like if your, if your stuff’s not resonating, you know, better for them better to know that then to do it for six months, you know, on zoom meetings or whatever. And the idea that 

Tom Wentworth: [00:31:50] my quick story was, it was, we were told that we should, this is back when Sarbanes Oxley was a thing and I was selling content management and we were told as se is [00:32:00] going to get out there and pitch our new Sarbanes Oxley solution.

Here’s your pitch deck? And we clearly knew nothing about Sarbanes-Oxley and you know, we’d been given some talking points that were just clearly nonsense. So we’re out there and pitching our Sarbanes Oxley solution to. You know, some sorta risk person at an insurance company like Aetna or Cigna. And they just said, this is a waste of our time.

This meeting is going to stop now. And, we had to do a long drive all the way back from Hartford to Boston and it was not comfortable, but it happens. 

Anthony Deighton: [00:32:31] Yeah, I’ll look it up. Moments like that are an opportunity to go back and do it right into 

Tom Wentworth: [00:32:37] until your product marketers. Yeah. That messaging didn’t quite work.

In fact, we were kicked out 10 minutes into our pitch deck. 

Anthony Deighton: [00:32:43] That is a, that’s a, that’s a, that’s a low bar. One that one should hopefully be able to hop over. But yes, fair enough. 

Tom Wentworth: [00:32:49] But it’s got to happen to you once. All right. So. After Clegg had a bunch stuff at click. And I think we talked about product managers, product marketers.

Then you went to Solonus as the CMO, and I know you’d run [00:33:00] marketing before, but what, what was your, what was the experience like going from product to, you know, all of a sudden now having to carry to manage a number and think about brand and comms and all these things that you probably don’t worry about as much as a head of product?

Anthony Deighton: [00:33:17] Yeah, no, I think it’s a great question. look, I think it was, it was, A fun challenge, that there are the central challenge for Solonus was how to invent a category, that helped them break out of the noise of what they call the category they were positioned in, which was called process mining. and, you know, that was, at its core that as a product positioning and product marketing challenge.

So. At some level, yes, it’s CMOs, but there was this core product marketing challenge at the heart of it, which was partly what was sort of intellectual. Interesting to me. The other side of it, from a pure career perspective is while I had done marketing at Klick, I had never, [00:34:00] owned. Demand gen. And, one of the great opportunities at Sloan is, and partly because it was a very new company, it was moving to the U S the U S operations were very small, was to take on the challenge, of building a demand gen function, and, and having the opportunity to do that.

From first principles, as opposed to working with a broken demand gen that needed to be fixed, which I think is maybe a harder challenge. and so I just. On a purely like fun perspective. That was a great challenge. And, and I was excited for the opportunity to dig into that. you know, the branding, marketing communications work, there were frankly, there was a big opportunity and requirements there as well.

That’s not my strong suit. And so I, you know, I had. you know, I augmented the team with people who are much better at that than I, and I think that, you know, so you, one does need to think about what one’s personal strengths are, versus, where you need to augment, yeah. [00:35:00] With, with, you know, outsiders.

Tom Wentworth: [00:35:01] Yeah. Dave Kellogg talked about that. He said there are three pillars of a great CMO. You can be great at demand gen and growth. You can be great at comms and brand, or you can be great at product marketing, but. You know, only, you can only realistically pick two there isn’t, you know, there there’s five people on the planet who might be great at all three.

And I know I’m a demand gen product marketing guy. Sounds like you might be as well. But, I thought that was an interesting observation. 

Anthony Deighton: [00:35:27] No, I think it’s a, it’s a various doot one and I would actually go further and say, you’re generally good at one. and, and you, you typically, so. and by the way, I think Dave is exactly right on the pillars, right?

it’s really, maybe I’ll call it a product pillar, a sales pillar, demand gen, and then a branding and communications pillar. and you know, it’s clear my strength is on the product side, so there’s no, I don’t have any doubt on that. and, and, you know, for me, you know, doing the demand gen thing, [00:36:00] like I said, it was a fun time intellectual exercise, but I absolutely brought in, I hired people and brought in and, you know, experts, people who are really good at that.

and certainly on the comm side as well, So it’s, it’s partly a question of self-awareness. I think the tendency for people, this is a more general truth, but the tendency for new managers is to believe that you only get credit for things when you do them yourself. So if your hands aren’t in the pie, that you didn’t make it and good and experienced managers realize that, that’s almost exactly a hundred percent upside down that in fact, Credit flows and credit to the extent that that matters, but, you know, credit flows to the team that achieves the outcome, the outcome, and to the leader of that team and great leaders.

You know, really use opportunities to, to point at the, the folks on their team that are, that have achieved those things, recognizing that building them up does not diminish them. In fact, it’s the opposite, [00:37:00] building them up, builds them. Yeah. 

Tom Wentworth: [00:37:01] It’s what creates the, I mean, it’s what creates the opportunity to go in and tackle the next set of challenges.

Right. So, yeah, we’re, we’re going through that now. We’re trying to record a future, you know, w we want to make sure we hire. We continue to hire. We’ve hired. We have really great people with a few years experience, but we need sort of in some areas like product marketing, you know, we want to bring in more experienced people so we can then elevate and tackle the next set of problems.

So it’s, some I’ve learned I’m super good at being able to hire people smarter than me. It’s not that hard to do in retrospect, but it makes me look good for sure. It makes us look good as managers. 

Anthony Deighton: [00:37:41] Yeah. And thinking about. Balancing one’s self. Like there’s a tendency for people to try to hire people that are carbon copies of them.

And in fact, what you should look for are people who, who balance you. And that I think is a, again, a sort of a new [00:38:00] manager fault or, you manage a mistake is, is to sort of look, look to copy themselves as opposed to balance themselves. 

Tom Wentworth: [00:38:07] And it’s a bigger point, but it’s also the fallacy of cultural fit.

Like we used to talk about cultural fit, eight years guy. I remember this explicitly at a company it’s like, we want to hire somebody. You want to get a beer with after work. And I’m like, and that’s fine. That doesn’t mean cultural fit necessarily. Or that might mean cultural fit. It doesn’t mean cultural add, which is, I think the real purpose of this find people that give us a broader perspective who can fill in our blind spots and.

I think that’s not a part of it too. Hiring people who are just like me is not what it’s going to take to build a billion dollar company, you know, 

Anthony Deighton: [00:38:42] completely agree. And I think, you know, it’s, I see that happening a lot. If I, I think you could almost, as an antidote to that behavior is to, when you’re looking for, for hiring, you look for people.

That are very different, that brings something unique and [00:39:00] special. yeah, obviously they need to be skilled and, and you want them to, to bring an expertise into whatever job you’re looking for them. But, but I always liked people that, Have something different that they’ve maybe they’ve done a different job or they have a particularly a unique hobby or their, or no, or they’re willing to sort of disagree in the interview.

That’s always something interesting who were willing to take a contrarian view. you know, it doesn’t mean, they’re always right. but it, if you can’t defend your thinking. To a teammate, especially one that works for you. You know, you probably, it’s probably not a very good, well held, held belief, you know, like that.

That’s not giving you some concern. 

Tom Wentworth: [00:39:41] And one in one, take a nap like in an interview and somebody comes and tells me all the things I’m doing well. Well, like I get, I get the spirit. You’re trying to be nice, but it’s also risky because I had this happen and it was things I hated. It was things that I’m like, I can’t wait to destroy this and break it.

Like somebody tells me your website [00:40:00] is so great. And I’m like, I hated every second. I look at it. so it’s a risky thing. I would much rather have somebody tell me what they don’t like and fight that then there’s no risk or there’s less risk for me. Yeah. 

Anthony Deighton: [00:40:11] And that’s not an excuse, for, for being rude.

I think that people, confuse disagreeing with being disagreeable. and you know, th there’s a really professional way to do that. and by the way, this also speaks to a related issue. There are two types of people in the world. There are a problem identifiers and problem fixers. and you know, I don’t know what the ratio is, but you meet people who are wonderful at sort of like making lists of problems.

and then you meet people who are. Dog it about fixing problems and I’m always attracted to that, to the latter. you know, the, the former make very good consultants. And I mean, I think there can be, especially in big companies, it can be really valuable to have people who are sort of good at sort of finding the issues [00:41:00] so to speak.

But especially in smaller companies and startups and things like that, you know, people who are like lack, latch onto something and then wrestle to the ground and fix it, that skillset, it, it requires obviously being able to identify the problem, but also this kind of dogged determination to try whatever it takes to get it fixed.

again, in interviews, I see that as well, like, you know, somebody can give you a long list of things that are wrong with your website. I’d be more interested in the person who sits and says, here’s the top five things I would do. Do differently on your website to make it better, like great. Those are the five things we can implement tomorrow.

You’re hired, right. Versus there’s a list of 40 things, which I don’t even know where to start to 

Tom Wentworth: [00:41:36] fix. So my last question for you, which, which touches a lot of these things, you sound a lot to me a little bit. I can consultant. And I’m going to guess. That’s because you’re a Harvard MBA guy and I’ve always been fascinated by people with MBAs.

I didn’t, I don’t know what the four P’s are still these days. I’ve never taken a marketing class in my life. but I, I would [00:42:00] love I, but I get asked a lot by people who are earlier in their careers about the value of an MBA. And I tell people to go for it. I think there’s value, especially obviously a Harvard MBA, but if somebody who’s gone through that now, and it can reflect, you know, what, what did, what did the MBA do for you and you think, you know, how would you, how do you talk about that to people that you advise?

Sure. 

Anthony Deighton: [00:42:21] I’d say a bunch of different things. so the Harvard MBA for me was incredibly valuable. and remain valuable to this day. but also understand and appreciate that I did it over 20 years ago. So my experience of it 20 years ago, versus what you would do and get today, I have a harder time commenting on that in the moment.

just cause I’m not, I’m not doing it. It, my, my apotheosis is that it’s, it’s still a very valuable, investment of time. My recommendation to people is to do the MBA sooner, rather than later, there’s a huge opportunity cost associated with taking yourself out of the workforce for a year and a half, two years.

you know, [00:43:00] I did it very young, relative to the, to the average. and I would suggest, you know, if it were, if I were advising someone, I’d say, if your decision between doing it this year and next year, do it this year. If it’s a decision between, you know, like the sooner you can do that, the better.

for the obvious opportunity cost. I also think that it generally is, in generally a master’s degree, in any sort of, higher education, which is high, typically highly specialized, in a focused educational experience is, is very valuable. and then the other thing that the MBA it gives you.

is, network and friends. and I don’t mean like, maybe friends is the wrong word. It gives you a network. and like-minded people who are interested in, in that case business. You know, if you do a master’s in, you know, in, in some other field that you’re, that you’re in, you know, you meet a bunch of people who are interested in that field.

and, and that, that group of people have been. You know, people I’ve kept in. I literally had a phone call with a business school. [00:44:00] Classmate middle of last week is doing a startup. you know, we were talking about all kinds of stuff that, you know, so like it’s a network you can tap into, on demand.

It’s been, I still do it to this day. and I find it very valuable. So I agree with your, advice to people which would mirror very closely mine, which is generally speaking. Yes, you should do it. But I would only add do it sooner rather than later don’t delay it. If you think it’s something you want to do, you know, get on it.

and, you know, and, you know, it’s generally, you know, the only caveat I would give is, you know, I did a long time ago, so, 

Tom Wentworth: [00:44:36] but it’s, it’s the skills you learn are the kinds of skills that give you a headstart, like understanding. The economics of business, like really, really what a P and L is, and like your, how your, how hard it is for your great idea to actually make money on a P and L and how to negotiate and all the things that like you can [00:45:00] learn through your career.

But, you know, it’s, it’s just, bootcamp, right? 

Anthony Deighton: [00:45:04] It’s you in a fairly focused period of time, you’ll get exposure to. A wide range. And in MBA, at least you get an exposure to a wide range of business topics. you, but naturally in your career will take one or two of those and get really focused on them.

so, you know, obviously for me it’s been marketing, but, You know, like I still think back to accounting classes I took or to finish dance classes. I took just a very random thing. when we took click private, we built a discounted cashflow analysis to think about the economics of that go private deal.

As we thought about, the, management incentive portion of the equity compensation. And, but you know, who built the, the DCF. Me, you know, like I sat down with this. I mean, it was literally like what I would have done, you know, in the first year of finance clause, the building a discounted cash flow for a deal.

Like it was, I [00:46:00] almost literally went back to, you know, templates, spreadsheets that we had, at the time. So like, those are skills that, that, you know, that you’ll have and, you know, you know, I don’t build many discounted cashflow analysis today. I hope 

Tom Wentworth: [00:46:12] not. 

Anthony Deighton: [00:46:13] In the rare event you need to, I, I have a pretty good understanding of, of what needs to go into it and I’ll pull that up.

So yeah, no, I think it’s, again, I, you know, I worry sometimes I’m a bit biased, cause I, I I’m thinking about MBA from 20 years ago, but I think it generally is a, is a very strong degree. That forms a really good foundation for anyone who’s interested in, you know, leading a company in the technology space.

Tom Wentworth: [00:46:38] Yeah. Well, I think in a lot of ways, you know, your career arc speaks for itself and sort of validates the approach you chose, obviously not the only way to do it these days, but, I think it’s, it’s still is a very valid way for people to think about their career. And, it’s a hard decision to make when you’re 22 and you want to.

Yeah, get onto the real world again, but it’s, for a lot of people I know it’s [00:47:00] worked out really well, so well, Anthony, thanks a lot for your time today. This has been fantastic. You’re a extremely well-respected, marketer product guy leader in the Boston area and around here at recorded future. So I really do thank you for taking time and this has been great.

Anthony Deighton: [00:47:15] Yeah. Oh my pleasure. And yeah, I look forward to hearing it on the interwebs. 

Tom Wentworth: [00:47:22] Thanks again, Andy. 

Anthony Deighton: [00:47:23] All right. Talk soon. [00:49:00] [00:48:00]

By Tom Wentworth

CMO at Recorded Future | Formerly Acquia, RapidMiner | I like math, open source, and the Smashing Pumpkins

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