CMO Confessions Ep. 24: Cherwell Software’s Scott Gainey

Hello and welcome to another edition of CMO Confessions. I hope everyone is gearing up for a great Fourth of July break, getting out of your respective homes and offices and enjoying some well deserved rest and recuperation.

For our Fourth of July edition of CMO Confessions, I sat down with Scott Gainey, CMO at Cherwell Software. Scott is a multifaceted leader with experience in the technical nature of business (how many CMOs do you know who can code in Fortan, C and C++?) and brings a holistic approach to his work.

In this episode, we sit down to discuss why marketing leaders must be able to show real progress in their work, how they can assess progress and how they can use data to make smarter marketing decisions. It’s a great episode with a lot of insight into the day-to-day of what a CMO actually does.

If you’re interested in what else Scott has to say, you can find his Twitter profile here. If you’re interested in his extensive background you can check out his LinkedIn profile here.

If you’re interested in listening to our growing podcast series, you can find all of our episodes right here in podbean. Alternatively, you can also find us on both iTunes and Google Play stores.

Without further ado, welcome to CMO Confessions. Let’s chat.

Table of contents:

How Scott got into marketing
What Scott thinks of marketing’s recent changes
Using data to make smarter marketing decisions
The importance of making, and sticking to, a plan
Shedding light between sales and marketing
Making Big Hairy Audacious Goals
Scott’s marketing passions
What grinds Scott’s marketing gears

Transcript

Joe Hyland:

Hello and welcome to this week’s episode of CMO Confessions, a weekly B2B sales and marketing podcast where we explore what it really means to be a marketing leader in today’s business world. I’m Joe Hyland, CMO here at ON24. And joining me this week, from the Denver area, is Scott Gainey, CMO of Cherwell. Scott, how you doing?

Scott Gainey:

I’m doing great, Joe. Thanks.

Joe Hyland:

Yeah. Thank you for the time. I’m excited. I’m excited for the discussion.

Scott Gainey:

Yeah, yeah, no, likewise.

How Scott got into marketing

Joe Hyland:

All right. So, I think, one thing that I get asked a lot of, and a lot of people on the show talk about this, is their path to becoming a CMO. And I think a lot of marketers, particularly younger marketers, naturally feel like there is a like a preplanned evolution that every head of marketing has for their journey. And I think that is seldom the case. So I’d love to hear about how you first got your head of marketing job or first marketing opportunity and what your path looked like.

Scott Gainey:

No, I definitely didn’t take that path. Let’s see, I was late major change. I wanted to be a sports doctor. I did a couple internships, actually did an internship with the Los Angeles Lakers, which was fun — almost a dream job if you’re heading down that path to being a sports doctor. But I actually decided I didn’t want to do it. I didn’t want to head down that path, so I did a last minute change.

I happened to take some programming classes in Fortran, C, C++ and Microsoft was recruiting on campus so I said, “I’m going to put my name in a hat and try and get one of these jobs that they were recruiting.” And that was kind of my quick transition and start into tech. I started out in customer support and worked. I was sort of the back line to the back line kind of that bridge between the escalation engineers and product management. And so that was kinda how I began my career in technology.

From there, I moved more down kind of an inbound path sort of stayed close to development, product management kind of along the way and picked up some experience in marketing. I think the first real foray was with a product I was working on that didn’t have any marketing support. So I had to write the initial set of collateral to go on and do the sales training and enablement. And thought, “Oh Wow, this is kind of fun. I sorta like this getting out of the office.” And then from there sort of picked up a little bit more responsibility towards marketing along the way. And I think I got…I’ll call it a break.

I got my first real break working for a company, Nuova, that was getting acquired by Cisco and we were launching a new product, an entirely new product, for Cisco. Then through the acquisition I got asked “Hey, you want to come over and be the first marketer for this new product line, UCS?” Which is this computing product line. And so I was, Marketer Number One and responsible for basically everything launching this new product, through Cisco and ended up building up a team from there.

From there I really never looked back, stayed outbound focused from that point forward. I took on another marketing head role at Cisco for their security business and then moved over to Palo Alto Networks to increasing responsibility there in the marketing group; product marketing, demand gen some of the technical marketing and then from there I was just kind of felt ready. I felt ready to step in and take a CMO role, which I did a the next company after that, took a CMO position at that point it was all on me and I had no one to blame but myself.

Joe Hyland:

Yeah. The job you’ve always wanted and then you realize, oh shit, it comes along with a lot of responsibilities.

Scott Gainey:

Oh no, I have to sit in front of this board and the rest of the leaders. Yeah. So that was the path. Yeah. I started out definitely more technical and then ultimately moved into more of an outbound kind of position.

Joe Hyland:

Yeah. Okay. That’s very, very interesting. And I always find it fascinating when people come up through the product side. You mentioned being more technical, my sense is, the better you can understand your customer, the better you can understand your market.

Truthfully, the better you understand your product offering the more effective marketer you are is I think a lot of marketers, particularly 10 or 15 years ago, maybe that was less of a concern. I’m seeing more and more marketers take a path like yours.

Scott Gainey:

Yeah, I agree. I think there’s this old misnomer that marketing is just simply there to make things look interesting, right? I have advised a lot of people who ultimately want to move into a CMO role. And I’ve always just said, get to know your customer, get to know your market, get to know your technology and what differentiates you first and foremost. Spend time, go invest in sitting with engineering, sitting with the SEs in the field, talking to customers who will talk to you.

I think that serves as the foundation that will only benefit you down the road. As you’re writing a press release or working on a presentation where you’re going to stand in front of your sales team at SKO. There’s any number of different outlets that you’ll get involved in as a CMO and having that foundation will really serve you well.

Joe Hyland:

Yeah. I think foundation is a great word there. Having a superficial knowledge of anything in life, I don’t, maybe you can BS your way through a few things, but ultimately you need real substance and depth and breadth and knowledge. I think the deeper you can go in any, in any space that you’re serving as a marketer, the more successful you’ll be.

Scott Gainey:

Yeah. Oh yeah. No, one hundred percent agree. One hundred percent agree.

What Scott thinks of marketing’s recent changes

Joe Hyland:

Okay. So, you referenced something that I love talking about, which is, how marketing has evolved and marketing’s role at many companies now, not all, but has really evolved over the last 15 or 20 years from the make it look pretty department to like the tip of the spear for growth. I’d love to hear how you’ve seen that evolution, assuming you agree and kind of what your day-to-day looks like in terms of driving growth.

Scott Gainey:

Yeah. I know. I mean I love where the role of CMO heads evolved in the last I’d say maybe even three to four years I think. And even as part of that evolution I think, what I’m seeing now is some acknowledgement that CMOs could actually take that step and ultimately become CEOs of their company. I think CMOs now have that seat at the table. We are there, we’re a part of the strategic planning of the company.

I sit with our board members routinely, I sit with, obviously, and work with, the executive staff regularly on just the strategic direction of the company. What are our imperatives? What do we need to do to reach our targets? Not just in this year, but in future years? And I think that being part of that conversation, being engaged in that conversation and bringing something to the table has helped in this role definitely evolve.

And I think bringing something to the table though is a critical requirement. And, and so I lean on myself and the team. We have to be experts in the segments that we want to target. We have to make those recommendations and bring that data into those strategy planning sessions. And so I really kind of evolved myself too. I’m a data mongrel. I, pour through, look at our customer base [inaudible] how is that segment, what is our historical [inaudible]…

What’s going on at a macro level with markets? Should we be focusing on in an area that we’re not today because indicators are that that could be a positive area for sure? And bringing in that information into the table. I think it just sheds a very different light on the role and what CMOs can provide as part of planning process.

Joe Hyland:

That was a great answer. There was a lot in there. I think I could talk for an hour just on the last two minutes that you just said. I think many marketing departments, as we both said, are becoming more strategic and you need your head of marketing to be leading that charge.

I was just emailing with one of our board members this morning on kind of his suggestions on some, he’s a creative guy, new markets we could serve, which is always interesting to have that discussion. But I think you’re head of marketing needs to be thinking about your go-to-market plan and kind of determining, or helping to determine at least, how you’re going to grow and how you’re going to operate as an organization.

Using data to make smarter marketing decisions

Joe Hyland:

I don’t see, kind of jokes aside, obviously your visual aesthetics, your brand, of course that’s still coming out of marketing. I’m just seeing so many marketing departments do so much more. And I love that you’re talking about data and how to use data and how to use data to make smarter decisions.

You reference living in spreadsheets, so do I. I’m not sure if I love it at all times. But I think as marketers become more and more kind of familiar and comfortable in that role they can take on more strategic positions within the organization.

Scott Gainey:

I mean it does begin with the brand. I come in, even to this company that I’m at right now, at Cherwell, we had a founding and leadership team that operated with many different taglines. There wasn’t [consistency], contrary to the message that they were delivering around the company, it’s hard to establish despite investment. It’s hard to establish a good sound brand if your executive team all uses different presentations, different messages, particularly to provide value to the company.

So you get to that continuity message, even your visual brand and identity in order to ultimately build strength into the market. And then from there as far as partnership with sales, I think a lot of CMOs tend to shy away from committee to numbers.

And I think we also live in an era where you gotta draw a line in the sand and say what marketing will contribute in terms of your business objectives. In our case, it’s all about new logo production, right? That is our sole focus is how many new logos are we going to bring in as a company thus what share can we capture year over year? And I set a challenge for myself and some of that was sort of suggested by one of our big investors.

But it made it a challenge. It made a commitment that the challenge that I got from KKR — as one of our big investors in the private equity houses — was that can marketing contribute 55% of those new logos that we want to attain this year? And there it becomes a spreadsheet exercise, right?

We follow the SiriusDecisions, waterfall process to reengineer waterfall processes. We work backwards and look at what our historic close rates are for opportunities in the funnel. Our conversion is from meeting the opportunity. What my conversion is from qualified lead, to meeting, from initial inquiry to qualified opportunity. And then that net was with the investments that we’ve made across the team and the change we made, I came back and said, “You know what? I can actually do 56%.”

Joe Hyland:

That’s crazy. I love that.

Scott Gainey:

But if you don’t live in the data, if you don’t take the time and energy to understand your historicals, your conversion rate, know where you are getting those contacts from and what investments are producing the best conversions down-funnel, then you’re going to be guessing on that, right? And the board, the leadership team, people are going to see right through that and you’re going to lose credibility instantly as a CMO.

The importance of making, and sticking to, a plan

Joe Hyland:

I love that you just walked through that process cause that’s actually something that I’ve never talked to anyone on the show about. I think it’s incredibly important for marketers to understand. Any great plan you, particularly if you’re growth oriented, needs to start at the number, the sales number. And then you work backwards and you work backwards based on historicals, conversions where you feel like you can get improvements. Then, from there that’s when you come up with your marketing programs and your creative ideas and how you’re going to see those improvements.

But yeah, if you just start there you’ll never truly be viewed as strategic. And it’s a fun exercise. It really is. It’s one of my favorite times of the year is planning for growth and then coming up with a model for how you can get there.

Scott Gainey:

I’d be happy to share this with anyone. You can always ping me over Linkedin, but I mean, I have three simple sheets. The first I get from finance that has our whole operating model, you contain it within a single sheet and including the breakdown of revenue. Next sheet is based on conversions, not just historical conversions but how we want to be better as a team. What that means is from top, middle to bottom of the funnel. And then the next sheet I’m also responsible for our BDR organization. Next sheet is okay, what are the expectations for our BDR team in terms of intercepting and converting those into meetings and ultimately qualified opportunities and that sheet everyone the whole leadership team gets? It goes into our KPIs on the year and we track it monthly as a team just to make sure we’re staying to plan.

And and it is interesting. We ended up writing it so our leadership team runs almost like a sales leadership team would run. We’re constantly looking at monitoring that data and determining from that do we make any course corrections, do we need to move money in an area? What do we stop doing? It takes honestly a lot of, I think the pressure off and tension that you might feel trying to hit some audacious goal when you’re tracking it and maintaining it that closely.

Shedding light between sales and marketing

Joe Hyland:

First of all that, that’s fantastic. That I have pretty strong opinions on this. I think that’s how every organization should be run. There’s full transparency and visibility. It sounds, from what you just described, that sounds like that would eliminate any BS that may exist between groups.

I think a lot of marketers struggle with this in terms of how to have a real productive relationship with sales because different organizations, different pressures sign up for audacious goals that mathematically make sense, eliminate the BS, have full transparency and then it’s a partnership versus what’s sales doing versus what’s marketing doing.

Scott Gainey:

Yup. Super easy. And then I display that in a very simple format. I mean, it’s a presentation. Five slides on the left; it’s key initiatives on the right. It’s KPIs tied to those key initiatives. And I think that the board and the leadership team appreciates the transparency because they know, okay, I know what you’re working on now cause I can see your key initiatives, I also know how you’re going to measure success and failure against those.

I think that’s mistakes CMOs of the past have made is not having that transparency in terms of how are we going to hold ourselves accountable to delivery? It’s very easy for engineering. Cause they do [inaudible], did you get the release out on time? Did you hit the features that you had planned ahead? Sales; it’s very easy. You’re driving to a linearity on your sales goals, customer support. A lot of organizations that across a company are held accountable to a regular set of KPIs and think marketing to have that seat at the table, yeah, you have to sign up for that too.

Joe Hyland:

Yeah. No. Yeah. That is very, very, very well said. And I love when an aggressive number was suggested to you, you said, “Let me go back and run some math,” but then you signed up for a point higher. And I think that just sends the right message of like, you guys are in it, like you’re in it for to sign up for growth.

Scott Gainey:

Yeah. I mean, I don’t know that my [inaudible] team loves it, but, you see, I want a number that makes you slightly uncomfortable as a team. It has to be grounded in real data. So that you actually have more than a chance of hitting those targets. But you should be stretching yourself every step of the way.

And then you can look at upstream indicators to truthfully see trouble before it hits. So, for us by segment, I have some strong opinions and MQLs, we’re still very much tracking them of course. For us it’s a sign of, are we in good shape for pipeline in a month or two or oh shit? Are we falling a little behind? So yeah, I think a mathematical equation helps to plan and helps to realize when you’re going to be entering troubled waters before you’re actually in troubled waters.

The only thing I’ll add, too, is I think there are shared aspects of what those goals are. But then I think it’s also important to bring those KPIs down to individual teams. So everyone will mention I have responsibility for BDR, I also have technology alliances. You know your product marketing function, demand-gen and then my corporate communications and corporate events. Those are the key functions across my organization and every one of those has a set of KPIs that map to what those top level objectives are that I’m sharing with the board and the executive leadership team. Don’t be shy obviously in parsing those down and holding those sub-teams accountable for what I say are sort of the pillars right there, the legs of the stool that you need in order to hit those bigger objectives.

Joe Hyland:

I couldn’t agree anymore.

Scott Gainey:

I don’t believe in soft soft goals, right?

Making Big Hairy Audacious Goals

Joe Hyland:

So for us two things for us. We call them north stars, which is, “What are our kind of guiding principles? What are the three or four things in our department that have to happen?” And then, underneath it, between and product marketing, demand-gen, corpcom, customer marketing. What are the key areas that they absolutely own to give us a shot in hell of hitting these big numbers.

I think goals are really interesting. It’s easy to misinterpret goals as well. I think a lot of people point to what Google did with OKRs. And so a lot of organizations now have these OKRs which are actually I think somewhat misinterpreted. People sign up for really achievable goals, the whole purpose if you go back to the original OKRs were stretch goals that so like stretch your organization, you shouldn’t be hitting 100% of anything. I feel like a lot of people miss the mark on that.

Scott Gainey:

No, I definitely, I love … if you ever have the opportunity, I went to a great leadership training program at West Point through their leadership development. And so these are courses taught by basically colonel or higher from a ranking perspective. And these guys used to always talk about this notion of BHAGS, those Big Hairy Audacious Goals, right?

It’s amazing, you set a BHAG for the team, in this case, beat 56% logo contribution. And you’d be surprised, right? How creative and intense people get in hitting those targets. And I think we had a gut check, I said, “Before I send this off to the board, I want to make sure that everyone … that we’re all on the line together and so set your big hairy audacious OKR and then let your team surprise you.”

Joe Hyland:

I love that. I’m familiar with that and I haven’t heard it for a while. Yeah, I think it’s, it’s a pretty simplified way of signing up for really aggressive goals. I think that’s great. Big hairy audacious goals. I’d forgotten that.

Scott’s marketing passions

Joe Hyland:

Well, switching gears a little bit it sounds like you’re passionate about a lot of things, which is something I just love in life. what are things that you love about marketing today? And that could just be like what we’ve talked about, like signing up for these big aggressive goals or really knowing your market really well. And then afterwards I’ll ask the conversing statement of what actually frustrates you and what drives you crazy about marketing. But you can start with what you’re passionate about first.

Scott Gainey:

For me, what I really like is, I think in this role and function, you really get to work across the entire company. We touch every part of the business. I mean, obviously we work with sales every day. So that is perhaps the closest relationship. But also closely with engineering, with our customer support organization, with professional services. I like the aspect that in the role you get to touch really all the different aspects of the business. I think you get a good bird’s eye view of how companies work at the end of the day.

So I like that. I appreciate that. I appreciate the customer contact too. I something I do actually for the team, every year I hold an event for my team and invite a bunch of customers in just cause not everyone on the team gets a chance to sit there and talk to and listen to living, breathing customers. And so I love the energy and excitement they bring, the realism. To me, they are the boots on the ground, they’re who we’re trying to market to.

And so I like that — certainly, particularly if you’re in a global role capacity. It’s exciting to me to see how different business is run and performed in, let’s say China compared to Mexico. Or Canada compared to the Middle East. I like that broadness. And the ability to kind of think about, from a how do you attack a market perspective, all of these cultural nuances that need to come into play.

Joe Hyland:

I think that’s wonderful. And I think it’s, I think that is a very smart exercise you put your team through. Not everyone’s customer facing, but it’s incredibly important that everyone understands the plight of the customer. And you’ve got to do something which is pretty simple as meet and talk to them to understand that.

Scott Gainey:

Yeah. It’s fun. There’s nothing like sharing a beer with a customer. Just, the information starts pouring.

Joe Hyland:

No, it’s true. We actually, just last night, we in the month of January, ran something called our Webinerd Appreciation Month, which is, we call our customer base webinerds, we are a Webinar company. And so we had every office, in five offices around the world, on January 31, we had we had this customer meetup is really all it was.

And so we had it in San Francisco yesterday and it was really cool seeing the person who writes the case studies on my team having a beer with a customer and I just, he doesn’t get that many opportunities to actually meet with customers in person, even though he’s writing these case studies. And I think it helps to understand the persona.

Scott Gainey:        

Absolutely, yeah. I think there’s absolutely a lot of goodness. I have no regrets. I wouldn’t change a thing in terms of the career path that I’ve taken and where I’m at.

What grinds Scott’s marketing gears

Joe Hyland:

Very cool. I would be remiss if I didn’t make you list a couple of pet peeves though. So, give me a pet peeve on marketing today because there’s obviously lots of them.

Scott Gainey:

I mean it may have more to do with the function, right? And just some of the historical, I’d say, maybe job descriptions I guess, I just always bugs me and maybe this might be symptomatic of just U.S. headquartered companies. But I always struggled with, and tried to overcome this, the difference that you see and get between field marketers based in the U.S. supporting a U.S. headquartered company versus the regional marketers.

I feel it right in Europe and Asia and I think there’s, there’s some historical aspects of that. And I’m trying to evolve just the notion of that role.  I think I’ve always said  if you’re a field marketer or regional marketer you’re one in the same. You’re in essence the CMO for your region. And so you need to be thinking not just about putting together some events, but you need to think about how do I build my brand in the region that I’m in control of, right?

Engage closely with partners; obviously with sales. You have to think of the full mix, not just getting contacts, but how do I build nurture streams against those contacts? Are the BDR team prepared and ready to receive the fruits of my labor in terms of new leads? And I just I think that is something that definitely I’ve tried to overcome with the last couple of companies has really changed kind of how they see their role going forward. So, I think that’s maybe more of a self created annoyance.

Joe Hyland:

I think you’re right though.

Scott Gainey:

Yeah. I mean, I think I’d be remiss if I didn’t complain about probably two or three emails I get each day from somebody that had great appointment setting opportunity. That or some lists that I need, right…

Joe Hyland:

Two to three it’s more like 30 to 40 every day. I mean, it’s literally an epidemic among marketers.

Scott Gainey:

I mean, the beauty is that the tools that are out there today that you can utilize are amazing, right? I mean, back when I think of what we’re using in just our BDR team with things like Outreach IO for data sequencing [inaudible] alerts and phenomenal for us that data clarity that we get out of things like Dun & Bradstreet. I mean just, it’s amazing what you have at your fingertips today.

You know, I think maybe one challenge that I face is still is marketing is a line of business within the company, is a large purchaser of technology. It’s a big part of our business, it’s how we get to build, develop very efficient, qualified leads for BDR and sales organizations. And I think I still struggle with just this balance of IT wanting to have control and say over purchasing across the company.

But it’s really hard, unless you live in this business world, it’s really hard to apply a filter unless you really know and understand the role of marketing. So I think it’s a balance, right? And working with IT. So it’s not, it’s not a nuisance but it’s just added work. So if I had to complain maybe that would be it.

Joe Hyland:

That’s not a wasp. It’s a mosquito.

Joe Hyland:

Scott, listen, thank you for the time. I think a lesson to be learned by any marketer is not being afraid to sign up for big, big targets regardless of the area of the business. So go sign up for big, hairy, audacious goals everyone and Scott, listen, thank you. Thank you again for the time.

Scott Gainey:

Yeah, yeah, no, I appreciate it. Thank you for having me.