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CMO Confessions Ep. 39: Deb Wolf of Integrate

February 18th, 2021 Andrea Bartman

We’re back with another episode of CMO Confessions, our B2B podcast with the top leaders in marketing and sales today. Today’s CMO Confessions features Deb Wolf, Chief Marketing Officer at Integrate.

In today’s episode, Deb and Cheri Keith, Head of Strategy and Research at ON24, discuss Deb’s new position at Integrate, the transition from customer to employee and what it’s like to join a new team during a pandemic.

As always, you can find the full episode of CMO Confessions on Podbean here an edited transcript of our conversation below.

You can learn more about Deb’s background and career path through her LinkedIn page and Twitter feed.

If you’re interested in listening to our growing podcast series, you can find all of our episodes right here on Podbean. Alternatively, you can also find us on iTunes.

Welcome to another installment of CMO Confessions!

Table of Contents: 

The Career Path to CMO
From Customer to Employee
Marketing to Marketers
Joining a New Team Mid-Pandemic


Cheri Keith:

Hello and welcome to CMO Confessions, the B2B marketing and sales podcast, where I speak with amazing guests about what it really means to be a marketing leader in today’s business world. I’m Cheri Keith, Head of Strategy and Research at ON24. On today’s episode, I’m joined by Deb Wolf, CMO at Integrate, a marketing orchestrate platform. Deb, thanks so much for coming on.

Deb Wolf:

Hi, thanks for having me.

The Career Path to CMO

Cheri Keith:

Great. Well, I usually like to start these by asking about what led you into the role of CMO. Very rarely is it a linear step-by-step process without either changes in a perspective or industry? So tell us about how you landed here, Deb.

Deb Wolf:

That is for sure for me. My career, which now is 30 plus years in B2B marketing started on the ad agency side of all things way back when tech was just not cool to be in. And most of the technology that we were marketing at that time was very technical and very “speeds and feeds” kinds of things. I was not a marketing major, I was an English major in school. I started in the ad world as a client manager, and really at that time we were doing mostly in the agency that I was working for mostly print and a little bit of billboards and things like that. There was no real demand gen back then, as I remember it. The demand gen was, if you go back that far, things like business reply cards that you ripped out of magazines. They’re still in all your B2C kinds of publications today.

I started there, and I did about 10 years on the ad agency side before I realized I couldn’t sit in a client meeting and actually say, “Hey, you know, when I was a client, this is how we handled things.” And so I said, “Okay, I need to go get some corporate side experience.” And I ended up working for PeopleSoft in the late eighties, early nineties and running their advertising program for them.

And then subsequently through the dot com bomb at Commerce One, if you remember one of the darlings of that time. A company way ahead of itself. I had a really good run there. This was in the heyday of spending just ridiculous amounts of money on advertising until about May 2001, when the floor just fell out. I think I had a $12 million advertising budget at that time and it really went to zero overnight, literally overnight.

Through a couple of different things, I found myself at a company called Mercury Interactive. Right during the time or right before the time that HP bought them. I was running their advertising and brands.

The early part of my career, I like to say was all on the advertising and brand side. And then I had the opportunity to go to Workday very early on. The company was only just a little over a year old. It really had been in stealth mode on their products. It was very early in cloud days. The only company doing cloud at that time was Salesforce. I took a role to be their first full-time marketing person. They had a name, a logo, three pages on a website and zero databases.

Overnight, my job changed from advertising and a brand that I knew and loved to demand. It was really an interesting time to be doing that because it was also sort of the heyday of all MarTech being born. This would have been 2006. The great news about going to Workday, at that time was they had nothing. The challenging part about it was they had nothing. So we built a website with everything from the MarTech stack, really from the ground up. We were very early Marketo customers. We chose a cloud-based CMS called Ingenix. We were running things like Google analytics very early. There were a number of different things that today you think of as the very foundational elements that someone would put in, that we got to experiment with.

We were doing lead scoring before that became fashionable. We were nurturing before that became fashionable. And so I had these, I call them my baby bird salespeople with their mouths open saying, “Where are my leads? Where are my leads?” And if you know the history of Workday, that company was really born out of the PeopleSoft-Oracle acquisition/hostile takeover. Workday was super careful about who they wanted to go after as customers and so building out that database was a painstaking process from the ground up. Reps didn’t come and bring their customers. We really built that database from everything that we did from a marketing standpoint.

I had the opportunity to grow with Workday from really zero revenue, zero customers, 60 employees when I joined to almost 5,000 employees when I left, a billion dollars in revenue through their IPO and a full stack in the marketing technology arena that we had implemented.

When I was finally ready to get off the rocket ship called Workday after almost nine years, and I looked back on the time I enjoyed the most there, I really thought that the first four years were the most fun for me. They were by far the hardest years. They were the years in which we were trying things. We were failing and trying other things and working very tightly connected with our sales team.

When I thought about what I wanted to do next, I wanted to go back into a company about that size and so I took a role at a mobile security company that was pivoting from being a B2C company into B2B. Subsequently, the two companies I’ve worked at in between Workday and where I am now, we’re in that 50 million to 100 million high-growth trajectory, as is Integrate. That’s the sweet spot for where we sit. And it’s really one of the most interesting times for an organization from lots of different perspectives. What is the business doing? What organization do you need to put in place?

Whenever I talk to folks that are coming right out of school and thinking about what they want to do, they always focus on the role they want to take. And one of the things I tell them is, “Focus on the kind of company you want to work for and the trajectory of that company.” Because your role as a product marketer in a very large organization like Workday, today at 15,000 people and a multi-billion dollar company and your role as a product marketer at a company like Integrate are two totally different roles. You need to understand which one you thrive in better. It’s not just about the pace or the things you get to do. It’s really about what the company’s problems are, what you’re trying to solve for, what their customer base is looking at, how close you get to people on the sales side, how collaboratively you can work with them and things like that.

I think I’ve identified that in myself. This is the size, strength and trajectory of a company that I like, which led me to Integrate. I joined in May. I joined as a three-time customer. I had bought Integrate at Workday, Lookout and BetterUp. I had followed the company and been on the customer advisory board, but I really had never done MarTech as a marketing executive. So the opportunity to help customers who are my friends is so, so fun. It’s such a great opportunity and it brings a whole new meaning to getting involved with sales cycles, product and really giving feedback from the team perspective that I just wholeheartedly enjoyed. That was a long answer.

Cheri Keith:

No, that’s awesome. I love it! Oh my gosh, there’s so much I want to dig into there. I’m an agency person at heart too. I’m going to say, I’m convinced that you’re really narrowing in on being at that high-growth startup, $50-$100 million comes because of your success working in agencies. You have a need for the corporate adrenaline that you can either get from having clients yell at you and constantly be pulled in a million directions, or you can have that in a high-growth company I think.

Deb Wolf:

It’s so true. You may be right. Both of the agencies that I worked at were probably somewhere in the neighborhood of 30 to 50 flexing up and down with people and size. And we had clients in those days that were in the $1 million to $2 million to $3 or $4 million sort of size range.

When I started in this business, the technology didn’t exist, right? The kinds of work we were doing in advertising when I first started, where we had very large boards and we were doing a black plate change meant you had to cut the type out of the board and put the type back into the board. And these things were three weeks long and $1,500 to do. Now, that can be done overnight or in an hour meeting today.

The change in technology that has impacted the industry has been so tremendous, but your point is well taken about that adrenaline of working on the business, right? Just really being involved in the clients and where the client is going. I always thought I’d go back to the agency business after I got just enough client experience, right? To be able to have that conversation.

One of the reasons I ended up staying was I figured out I was a pretty good client for agencies and helping them get the most out of their relationship with the client. Agency life is hard. You never really know what is going on within the walls of the client. You’re always trying to sell them something and help them along, but you don’t always have the full picture of what’s going on within the organization. So being an effective partner to be able to do that can be really challenging. I imagine these days, even more challenging when clients aren’t even in the same building together.

From Customer to Employee

Cheri Keith:

Yeah. There’s a lot of consensus building, to say the least, that has to happen when you’re on the agency side. The other thing I want to talk about with your background is going from being a customer to working at the company and the transition of it. I mean, you know the product better than probably most within your company in a lot of ways having actually used it out in the wild and in an internal sandbox. So can you talk about what that’s been like?

Deb Wolf:

Yeah, it’s an interesting thing being the CMO, right? I was fortunate enough that the marketing operations person that I have had with me since actually we met at Mercury Interactive and he’s come with me at every single job since then, would be the right user, right? He could tell you everything about the product.

I can tell you the value and I think that’s a really important distinction when you start thinking about the different personas that you’re marketing to as well. So I am not a hands-on-the-system kind of person, but I can tell you the value that we get out of Integrate every day. That’s where I try to hold the conversation with the customers. There are lots of things that you’re going to learn about the product from a usability standpoint, from how we can help you from a services standpoint and what you’ll actually be able to do.

But ultimately what I can tell you about are the things we’ve gotten out of the value of the product. How does the aspect of clean data impact the performance of all of our campaigns? How does the ability to understand what we’re getting from each of our different channels act as an altimeter or a compass to tell you which ones we should be investing more in? And that I think is sometimes missed at the user level. And those are conversations that I really love and enjoy getting into.

Coming from the customer side and switching to the CMOs side at the MarTech company is a really interesting opportunity from the perspective that as a customer you always think about when you start a new role, you have about 90 days before you really start sitting in your own soup. And you can’t think about it from a clear perspective or customer perspective.

Being the CMO, I’ve tried to really keep those relationships going with people that were me, the customer, outside of my day-to-day at Integrate because it helps me keep a clear head about what our product does, what the landscape looks like, how much marketing technology there is out in the world today that we’re throwing at marketers, what they need, what they don’t need, how we get really honest with ourselves about that as marketers and as vendors. Hopefully, it allows me to provide a perspective internally that’s still more customer view than it is CMO view of the company. That’s really what I try to do, especially when I get the opportunity to spend time with customers and really help our engineers and developers understand what the challenges are that marketers are facing every day.

Marketing to Marketers

Cheri Keith:

Well, that’s interesting because “marketing to yourselves” is something that when I talk to other MarTech CMOs, that’s something that comes up. And I think you’ve touched on it from a relationship standpoint, but also I think your ability to impact the performance of the work that’s being done internally is important. Oftentimes, we lose sight of that concept of marketing to yourself, unless you of course have a wildly specific case or industry in MarTech. This is your first time doing marketing to marketers, so has that been a good transition?

Deb Wolf:

Yeah, it’s fun because oftentimes they’ll send things back to our revenue marketing team and our demand and digital team that I’ll say, “Would you guys open this? Honestly, would you open this email? Would you click on this ad?” We are marketers. We should talk as normal as marketers talk every day and stop losing ourselves within the lingo and the crazy language. So getting really honest about that and finding our voice and making sure that we’re not blowing smoke. There’s not a better word I can think of to describe sometimes how lost we can get in our own messaging. We have an ongoing KPI around Integrate on Integrate using our own software. We’re using our own solutions and making sure that we’re giving plenty of feedback to the development team and working very closely with our campaign management team.

One of the things that when I’m interviewing and we’ve been building out our team and bringing a new team in and up-level some of our talent. And one of the things I say to them is, “You have an extra responsibility here as a marketer. That responsibility is to go talk to the salespeople, to go talk to the developers, to go spend time with customers, to help them understand where you’re running into challenges or where you hear from a competitor that they’ve got a solution that might be similar to ours, or at least positioned in a way that’s similar to ours.”

I would say for every person that we’ve brought onto the team, they’re excited about that. They’re energized by it. It’s an enthusiastic responsibility and it’s really created a cross-pollination of idea generation as well. Just to think about what are the use cases that we just don’t have a solution for today, that we could either be using our own product for or that we could take our roadmap in that direction.

Joining a New Team Mid-Pandemic

Cheri Keith:

That’s really cool. The other part that you brought up about your role is you started in the middle of a pandemic. So can you talk about what it’s like getting up to speed? I mean, meeting people for the first time in this manner, how has that been as a marketing executive?

Deb Wolf:

It’s interesting. I’ve done two board meetings now, so I’ve met the board members remotely. I had, of course, known Jeremy, our CEO. I had known some of the salespeople and our campaign management folks that had worked on various different accounts where we had purchased Integrate. But I had met them in person and some of them I consider very good friends. I’ve known those people for a very long time. But there are many people on my team that I did not know.

We’re headquartered in Phoenix with offices in the Boston area, in Hopkinton, and then in London through an acquisition we made last year. And we have a development team in Birmingham, Alabama. I have not had the chance to go to any of those places. I have not seen our corporate office. I have not been to our Hopkinton office. I haven’t been to London.

As I was making the decision to come to Integrate and making the decision to be a full-time remote employee, all of those things were considerations around how much time I would get to spend on the road and how often I would be traveling.

As a remote employee for the first time, a full-time remote employee even after times change, and we’d go back into offices, the idea of traveling to those places is super exciting. I was looking forward to spending time out in the field and spending time with customers, of course, but none of that’s happened. So you are building these relationships and trust one day at a time, one Zoom meeting at a time on an ongoing basis of trying to build credibility and trying to build trust with your team. I think you have to put extra cycles into what that looks like and how you coach people through it as well. How you coach managers that you’re hiring, who are also just meeting teams for the first time.

There’s a lot to be said about the resilience a marketing team can have during this kind of environment. The opportunity to get up every single day with Slack and email and all our tools that we’re on. It’s an interruptive culture.

We just did a very interesting exercise around psychological safety on the team, because many of our people are new and building that psychological safety around how we want to act as a team. How do we want to be as a team? How do we want to treat each other in this environment? It’s totally different than getting together in a room and then going out to dinner and having some cocktails and being able to really share, right? You get maybe an hour and a half to do it. My team’s so big that I can’t see them all in one window. So running through some of these exercises is challenging. There’s no doubt about it, but we’re no different than anyone else.

I think the wonderful thing about what we’ve seen from marketers across the globe, especially in B2B, is this “Get up and get it done every day” mentality. We’re going to be the industry that leads this world back out of the economy and the recession and things that have changed. I think the will to keep going and for people to feel really good about what they’re doing happens on a minute by minute basis at work every day,

Cheri Keith:

It’s definitely not easy, but you made that decision. We had been somewhat in quarantine for a little bit of time before you joined. The crazy thing about when I joined ON24, it was right before it all happened. So I came on board, interviewed in a very different world than we are today. My role has dramatically changed since coming on board.  If I think back to when I started, I was at the corporate office in February, and then I started in March with my first week on the road in Texas, actually, and then I was supposed to fly to San Francisco for my onboarding. And that was the Friday it went into lockdown. So they were like, “You can’t come out. It’s a little shifty out here.” I’m like, “I think it’ll be okay.” And then everything changed and the office shut down. So it’s crazy.

I’m definitely going to research more about the psychological safety because that sounds interesting. I always wonder because I’m the new person on the team. I mean, gosh, I have a very distinctive personality. I’m very outgoing and I’m like, “I hope I’m not coming across as crass.” And I feel like just saying like, “When you know me in person and you’ll know it’s [blip].” Yeah, exactly. So it’s almost like once we do get to meet all of our team members in person, that’ll almost contextualize the relationship in a different way.

Deb Wolf:

That’s right. That’s right. Of course we wonder about what everything’s going to be like when whatever normal comes back and we talk about this a lot around in-person events and what are in-person events going to be like? When are they coming back?

We just finished some research on that topic and there’s been no bigger impact in marketing, I think, than to the in-person event manager, right? The person who really focused on “My job is to get everything onsite working. I work with these kinds of vendors. I do these kinds of things. I’m concerned about what the after party’s going to look like, what the F and B looks like.” I mean, you name it. Those roles changed overnight.

When you think about the new technology, the new vendors, the relationships that I’m sure ON24’s built with people like this who have never thought of themselves as digital technologists before. I think one of the most interesting and unique parts around in-person events and virtual events, and what will happen going forward is that we know now there’s going to be a hybrid world. It’s 100% going to go there. We saw it in the research that we did.

When you think about the new skill set that folks are learning and the kinds of shifts in what they’re doing. All of a sudden, these events have gone from being kind of out on their own as a siloed disconnected part of a customer journey to being really connected at the heart in to the digital journey.

By the way, same thing for salespeople and what kind of relationship that you have with a sales person. I mean, do they come to our office again or do we do these kinds of meetings that are online? I think lots to work out through that.

When we think about those events and the future of what they’re like, you start thinking, “Wow, I really need to plan for two events now. The in-person one that we go back to and the virtual version that somebody is going to expect, because that’s now our new normal. For marketers, that’s planning two events, quite honestly. That’s like a whole different skill set, a whole different process to drive content through all of that. So it’s going to be a very fun and interesting way to reemerge when we do. Hopefully at some point in 2021.

Cheri Keith:

Yeah, absolutely. I think the event marketers have been the ones who’ve had to change the most. Their attention to detail is always what impresses me and I think the very forward-looking ones that have embraced this have excelled. I have friends that are event marketers that have gone through the training to get more up to speed on the rest of marketing, to be able to expand their toolkit, just knowing what the future holds. So that definitely resonates for sure.

Deb Wolf:


Cheri Keith:

Well, I want to thank you Deb, for your time today. I know I’ve enjoyed our time together. I’m definitely going to do some more research about psychological safety, but I think everything you shared about your background and this whole idea of working in MarTech in marketing and the additional hats you have to wear is really an exciting one that I’m sure our audience will enjoy listening to. So thank you, Deb, for your time. Thank you, CMO Confessions Audience, for tuning in.

Deb Wolf:

Thanks so much.