From Invisible Problem to Must-Have Solution : Melton Littlepage, CMO, 1Password

7 Mar 2025 · 34 min

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In short

Podcast Summary: The CMO Whisperer - Episode with Melton Littlepage, CMO of 1Password

Episode Overview

  • Podcast Title: The CMO Whisperer
  • Episode Title: From Invisible Problem to Must-Have Solution
  • Host: Steve Olenski
  • Guest: Melton Littlepage, CMO of 1Password
  • Description: This episode features Melton Littlepage, who discusses the journey of category creation in marketing, his experiences at 1Password, and insights into effective marketing strategies.

Key Themes and Discussions

  1. The Importance of Category Creation
  2. Understanding Customer Problems:
  3. Buyers typically wake up driven by urgent problems, not a desire to purchase software.
  4. Many prevalent issues lack a name or a story, rendering them "invisible" or unaddressed.
  • Creating a Language for Problems:
  • Effective marketing begins with articulating the problem clearly, allowing for the definition of a corresponding solution.
  • A new category is defined by naming the solution to a recognized problem.
  • Marketing’s Role:
  • Marketers must frame the story around the buyer's problem to foster connection and trust.
  • By doing so, buyers become advocates for both the solution and the category, leading to organic word-of-mouth marketing.
  1. Challenges of Product-Centric Marketing
  2. The Focus on Product Features:
  3. Many marketers default to marketing product features rather than the solutions those features provide.
  4. This can hinder businesses, especially when entering new markets or categories.
  • Case Study: 1Password:
  • Initially established as a consumer password manager, 1Password evolved into a business solution based on market needs.
  • The transition involved creating a new category, termed “extended access management,” to address the unique challenges of modern work environments.
  1. Launching a New Category
  2. Market Research and Development:
  3. 1Password recognized the gap in managing personal devices and applications in a remote work culture.
  4. The necessity for a solution that secures non-company-managed applications was highlighted, leading to the creation of a new category.
  • Communicating the Solution:
  • By coining the term "extended access management," 1Password successfully conveyed the solution's purpose, enhancing market understanding and accelerating the sales cycle.
  1. Sponsorship and Brand Visibility
  2. Sponsoring the President's Cup:
  3. 1Password sponsored the prestigious golf tournament to elevate brand visibility and connect with potential customers outside of traditional marketing channels.
  4. They leveraged data-driven insights to guide their sponsorship decisions, ensuring alignment with their target audience’s interests.
  • Impact Measurement:
  • Post-event analysis focused on website traffic spikes and promotional offer redemptions.
  • Although challenging to measure direct impact from brand visibility during the tournament, anecdotal evidence and sales tracking provided insights into the campaign’s success.
  1. Lessons for Marketers
  2. Aligning Internal Stakeholders:
  3. Successful marketing initiatives require buy-in across the company, including from the CEO and other key executives.
  4. It’s essential to frame marketing efforts as strategic rather than isolated activities.
  • The Leap of Faith:
  • Acknowledging the uncertainty in measuring new initiatives is crucial.
  • Building excitement within the organization around marketing strategies helps foster a culture of innovation.
  1. Melton’s Career Journey
  2. Path to CMO:
  3. Melton's career transitioned from engineering to project management, then to product management before entering marketing.
  4. His diverse background provides a unique perspective on integrating product development with marketing strategies.

Conclusion Melton Littlepage’s insights offer a compelling look into the nuances of marketing, the importance of category creation, and the effective use of brand visibility in driving growth. His career trajectory exemplifies the value of diverse experiences in shaping successful marketing leadership.

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For further exploration of these insights, tune in to the full episode of The CMO Whisperer featuring Melton Littlepage.

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Transcript

Automatic transcript. May contain errors.

0:00Hey, welcome to the CMO Whisper Show. I'm your host Steve Olenski. Part marketing practitioner, part ad agency veteran, part journalist. I was a writer for Forbes for 10 years. I've had so many insightful conversations over the years with business leaders, to athletes, to celebrities, to, of course, CMOs. The only difference now is instead of sharing those insights through written form, I'm doing it this way. My guest today is Melton Littlepage, CMO of 1Password. Trusted by more than 100 ,000 businesses to protect their data, 1Password gives you complete control over passwords and other sensitive business information.

0:39Melton has a 20-plus year track record of innovation, category creation, and growth acceleration at innovative technology companies. Prior to joining OnePassword, Melton was the CMO of Outreach, the leading sales execution platform, helping individual sales reps and whole revenue organizations create more pipeline and close more deals. At Outreach, Melton led the global teams responsible for strategic communications, brand, demand generation, customer expansion, product marketing, community, and sales development. And finally, Melton, his wife, and his three labs live in the suburbs of Washington, D.C.

1:14Melton Littlepage, my friend, welcome to the show. Hey, Steve. It is awesome to be here. Thanks for having me. You are more than welcome, my friend. I had a great time chatting with you off air. We are definitely kindred spirits. We're going to have a blast here. We're just going to have a conversation and hit record. So here we go. Okay, let's do it. I want to start with category creation and building in a new category, right? So I've interviewed other folks who in other industries launched or got into a new category and a challenger brand, things like that. So talk to us about the category creation and the importance of building and marketing and building a new category.

1:50Well, I mean, it really starts with the idea that no buyer wants to buy software. They don't wake up and say, I really need to buy this thing today. Instead, they wake up 10 minutes before their alarm goes off with their heart pounding and saying, this problem is killing me. I really have to get on top of this. But a lot of times that problem doesn't have a name. That problem doesn't have a story behind it. It's something that is in their business that is a job to be done. But it may be an elephant in the room. It's something that people have taken as for granted. like, oh, yeah, well, I mean, you just can't solve that.

2:30Or that's just the way things are in our business. Or maybe people have tried in the past to tackle it. And it turned out to be the thing that tanked their careers. And so there are these things out there that are big and gnarly. They cause a lot of pain in an organization or in someone's private life. And they just don't have... They don't have a language to talk about it. They don't have a framework to say, my problem is real and it exists. And here is a realistic way to solve it. And that there isn't a journey you can take that person on to bring them from that problem to your solution. And so the purpose of category creation, and this is, I've become a student of it, a sort of a disciple of some really great category creators that I've worked with.

3:15But the principle of it is, is building a language around the problem and the pain and the consequence of having that problem so that people can talk about it. And then if you can talk about the problem, you can actually describe or name the solution, right? And the name of the solution is the category, right? And so that's the, if someone is out there, it's like, well, I don't get it. What is a category? Then fine. A category is naming and claiming the solution to a problem. But what's most important is recognizing the problem, defining a solution for it that hasn't existed in the past, and then creating a language set that captures all of that in a way that you can easily communicate it at scale to the people that have that problem.

3:59And so the reason marketing does this is because it's very much a marketing challenge to present the story in front of the buyer in a way that the buyer is going to get it. They're going to believe it's like, wow, you must know more about this problem than even I do. And I believe that you can solve it because you can describe to me my situation better than I can myself. So if you can do all of that, then you're going to have that buyer on your side, not just as a purchaser. I market SaaS software. So not only will they become a subscriber to your product, they'll actually become a believer in the category.

4:37They'll tell their peer group. They will evangelize even though they don't know they're an evangelist because it's just remarkable. It's like, hey, for the first time, I'm able to do this thing or solve this problem or make this pain go away. Let me describe the painkiller to you. And so the word of mouth becomes like this really important, really invisible wind in your sails. And the person you sold to, they also need a language to be able to describe to their peers the problem and the solution. And so again, the category plays a really important role. We all know is word of mouth, but word of mouth needs the words.

5:15And so the category actually describes the problem, the solution, and the reason to believe all in one. It's a really useful tool. It really is. And I'm listening to you and I'm such a big believer in just keeping things simple, right? And one of the things that drives me crazy, and I want to go out on a limb and say it's for you as well. When marketers try to market, promote, sell, pick a word, a product instead of the solution to the problem, the product will solve. If you just look at it, you just said it, it was perfect, right? But you and I both know there's so many out there who are just pushing product, product, product.

5:49Well, it's because the product is what you know. You're an expert in the product. You're in the room with the product managers and your visionary CEO. And you're listening to the strategy. Here's why the product is what it is. And here's why the features are what they are. And so as a marketer, you're like, oh, great. I'm like, I'm totally bought into this. I just want to tell that story. And so product marketers, and they play a critical role in businesses, but they tell the product capability stories and the value of those capabilities. And so it pushes the product out into the market. And that's important.

6:25And it plays a really critical role in supporting sales. And if you're in a well-established category with other competitors and you need to prove differentiation, that's really one of the only tools you have for establishing differentiation. But if your product is new, it's the first of its kind, describing what the features are, isn't all that helpful because people don't even know if it's for them or not. And they don't understand why that feature is valuable. And so if you're breaking a new ground, if you're trailblazing, there has to be a different way to do it. A great example of 1Password, we were one of the first password managers.

7:02We started our life as a consumer password manager. We enjoyed great product market fit. And the product did exactly what you would expect it to do. Very securely stored, signing credentials to websites and applications, and then made it convenient to share them. Our customers brought us to work. And so we became a business password manager. And so we became number one in both sides of that category, both on the consumer side and on the business side, established a reputation over 18 years of being just the best at delivering that capability. But we're just on a journey, right? That's act one, consumer password manager.

7:39Act two, business password manager. And we're on to act three, right? Because what we've learned from listening to the market and listening to our customers, listening to security teams and businesses especially, is that they're vexed by the shift from work in the office to work from anywhere. And they're having a struggle as there's been this explosion of SaaS applications and new tools like ChatGPT, where the employees who now work from home sometimes and work from anywhere, they're feeling empowered. They have this permission to use the apps that are going to make them absolutely the most effective and productive in their job and who can argue against productivity.

8:19But it's bringing applications in that the business didn't buy and they can't manage and they can't secure. And likewise, people are bringing their favorite device. Who doesn't use their iPhone or the Android phone side by side with them when they work from their business provided laptop? And so security teams just don't have an answer to these. And this is just like we just live this every day, right? We all, almost everybody in your audience can pick up their laptop and take it with them wherever they go. And they probably also have a personal device, whether it's a phone, a tablet or a computer that they use as well.

8:52So this is the elephant in the room in our industry, right? So we all know what's happening. Technically, it's against policy in most businesses, but those businesses are turning the other way because they know that the employers are going to do it, whether it's in policy or not. And so that's what's keeping them up. I talked about waking up before your alarm with your heart racing. What happens if there's a data breach on an application that employees are using with customer data in it that we don't even know exists? That's their heart attack. And so we pioneered a solution that discovers all of those applications that are in use that aren't company managed and secures them.

9:29It's great. It's super simple. It performs a very important function, but it's never been possible before. And so there's no language for it. There's no way to describe what that is. And you can't even describe the problem very easy because there's not a language for permitting the use of SaaS apps that are chosen personally by an employee that are outside of policy but permitted. Right. And so we had to invent a language for that and coin a category name that was really the umbrella that housed the description of the problem and the consequence of the problem, data preaches, ransomware attacks, and then tie that into a solution that is realistic and simple.

10:12And so we launched a product in a category at the same time this year, which we coined as extended access management. And it was very specific and deliberate. it, there's an established category called identity and access management. And it is securing the applications the business owns and manages and the devices that the business owns and manages. So we said, okay, great. We need to extend those security measures over the devices the business doesn't own, personal mobile phones, for instance, and over the applications the business doesn't manage. Somebody bringing Figma in or Monday in or Asana in from the edge.

10:50And so we just said, okay, that's extended access manager. We're just extending what is great in the old work from the office days. And we're extending it into this new distributed workforce work from anywhere world. And as soon as we said that, it made sense. We can go to any security team and say, we offer extended access management and they know what it is before we even describe what it is. Even though it's never existed before. And when we describe the pain points in their business, they're like, yes, we have that. We don't talk about it. Yes, we tried to write a policy to make that go away.

11:20Couldn't do it. And then they immediately lead to, can you solve that? And we're like, yeah, our extended access management solution solves that. And so we're immediately 60 % of the way through the sales cycle. They're basically to the point of demo it, give us a proof of concept, let us pilot it, or straight on to purchase. And so we couldn't have done that without creating the language that would resonate with the buyer. And just being able to name and claim the problem is it was as important as being able to label the solution. It's fascinating because you've got, there's no precedent, right?

11:50You're launching a whole new category and that's take some, you know, the, what's the old adage of the first one through the door always gets bloody, right? So I would imagine it's the same thing that holds true here. First one in the new category, you're going to take some hits because you have to explain what the category is in the first place. And that's why we took great pains to make the category name as intuitive as it can be. That's step one. Step two is dragging our competitors into the category, whether they want to be there or not. And so if you think about the competitive battleground, any deal, there is likely to be the favored vendor.

12:27They're in column A. But normally, if you're doing a deal of any size, the company has to have column B and column C, a vendor shootout. And so we can actually pull other vendors in and say, like, we not only created the extended access management category, but we have the strongest extended access management solution. Let us show you a comparison of our extended access management capabilities to our competitors. And of course, our competitors don't have it, but they have pieces of it. Right. And so you can show a highly complete solution against an incomplete solution. And that just opens the eyes of the buyer.

13:02And they're like, OK, this is a real problem. We have this problem. There's a real viable solution. Other companies have implemented this viable solution and have achieved all of the benefits described. And it's the best of all of the options. And so therefore, I have confidence. This is a high value, low risk purchase. And that's how we get it done. Interesting. I want to switch gears here because you guys did something earlier this year that was really interesting. And you sponsored a golf tournament. And for those who are familiar, it was the President's Cup, which if you're not familiar with the President's Cup, allow me to elaborate.

13:34It's a series of men's golf matches between a team representing the U.S. and an international team, the rest of the world, except for Europe, because United States and Europe competed in the Ryder Cup, if you're not familiar with the different cups within the world of golf. So OnePassword sponsored the President's Cup. How did that come about? What was the rationale behind that? I think it's important to share that I'm truly a data nerd. And so if you work in my organization, you know that one of our values is be data-driven in every decision. Always start from the facts. and work your way out towards hypothesis.

14:07And so we know who our target buyer persona are in our consumer business, as well as our B2B business. And I think it's important to mention, like I said it before, we have millions of consumer customers. That's the roots of our company. And then more than 100 ,000 B2B customers. And those are both really important lines of business for us. We have well-researched buyer persona. And we know how to reach them through digital marketing. We know how to find the people that are currently in the market and pull them into our demand capture traps. We don't have a proven path to do is go find the people that aren't in the market now and rattle them.

14:45Give them a good hard shake and see who we can get off of the sideline and into the game. If 3 % of our potential buyers are going to buy in the next 12 months and 97 % are not, it's really meaningful for us if we can get that 97 % on the sideline to be 96 % on the sideline. There's 1 more percent entering the market that could increase our growth by 25%. The numbers are huge if we can pull it off. And so we hired CAA Sports, which has a tremendous media research arm. And we gave them our persona documents. And we said, research these buyers and figure out where they are when they're attached to their passions, when their heart is engaged, but they're not in the office.

15:28And what I mean, their heart is engaged. The reason I like sports, especially marketing inside of sports when you're in a software company, is there's not a lot of passion for SaaS software. There's a huge amount of passion for the team you root for. It's an unnatural amount of passion and commitment to a team that A, may not be that good. B, maybe something that you personally are frustrated that they make the decisions that they make. But your heart is so invested in it that you're going to watch the games, you're going to wear the jerseys, or you're going to go to the events. It's irrational, but it's real, right?

16:06Well, in marketing, we know that a lot of purchase decisions are like that too, right? You choose to buy with your heart and then your head justifies it. When you're a sports fan, you're a sports fan with your heart and sometimes your head can't even keep up. And so we wanted to integrate sports into our marketing programs, but we didn't know where to start. We hired this agency. They researched all of our persona and they came out with a scored list of types of sports. And then within the types of sports, the actual activations that had the tightest fit between our buyer and a sponsorship opportunity.

16:42And golf turned out to be one of the highest potential sports for us. And in fact, sponsoring a golf tournament was the highest scoring in the golf category because it puts you on a stature. Golf tournament sponsors are Coca-Cola and BMW and Dell Computers and Accenture and AT &T. Like those are the that's the elevation of the brand that we have the potential to be at that altitude and be seen as peers of these Goliath category leaders. That's what we wanted. right? Changed the entire market's perception of what our brand is and how influential we are. So we went down that route. And being a proud Canadian business, we're one of the largest Canadian startups in Canada's tech history.

17:25We had the opportunity to sponsor President's Cup, which was played this year in Montreal. And it was just too good of an opportunity to pass up. There's always 3 sponsors to President's Cup. The other 2 sponsors were Rolex and Cognizant. And, you know, if I had the opportunity to put myself at a level playing field with Rolex, one of the premium B2C brands, and Cognizant, you know, an elite B2B brand, that fits both sides of my business as the consumer business, you know, it's like we, our price point for consumers is nowhere near Rolexes. But that's an awesome stratosphere to be in. And then with Cognizant on the B2B side, I would love for people to think that we had that type of global clout.

18:04We basically borrowed as much brand equity as we could from our peers. And then by being a title sponsor, we just were blanketing the television coverage. Our brand was in the background in a tremendous number of shots throughout the weekend. We knew our buyer was plugged in and watching all four days of the tournament. And then we had the opportunity to have a lot of fun because our sponsorship gave us a commercial airtime during the live broadcast on Golf Channel and NBC. So we were able to actually film a fun and whimsical golf-related commercial tied directly to President's Cup, which told the simple stories about people having bad password hygiene.

18:43So reusing your passwords, writing your passwords down in a book, or saving them in your browser. The things that were a triple bogey in our commercial, we could have a lot of fun with, but we were able to relate it directly to the audience we knew we'd be watching. And then the commercials played live during the tournament. So they didn't cut away to a commercial where someone could run to the bathroom. They did this side-by-side where they would show the tournament on the left, the commercial on the right. And so there was no escaping it. And so it was a win for us. As a company that is uniquely consumer and B2B, although we were targeting our B2B buyer, we knew that the commercial would overspray millions of other audience members, whether they were at the tournament or watching on TV.

19:27But the million of people that it oversprayed scored extremely high in fit for our target persona. And so we almost couldn't miss, right? Like if we only a consumer business running that sponsorship in those commercials probably would have had a pretty high ROI. If we were only a B2B business, we know that targeting our B2B buyer with those messages would have a high ROI. But being both made the golf sponsorship like a can't miss opportunity. How are you measuring this? Well, you sound a lot like my leadership team. You did not put me up. I'll share the same thing. This is an active internal conversation because it's hard to measure.

20:07We could see right away the website traffic spike. Okay. We created a special offer for people watching the President's Cup. And so we can see the redemptions of that special offer right away. We knew who we were hosting because we had a tremendous VIP hospitality experience. on course throughout the weekend. And so we knew how much pipeline entered the course throughout the week. And then we could watch that pipeline either close one or close last, you know, since it's now been, you know, a couple of months. And so there's some things that are directly measurable. It's honestly really hard to measure the impact of the commercials and the impact of the sort of organic pickup of our brand in the television broadcast.

20:51Everybody's phone blew up with friends saying, I saw 1Password all over the TV. So we know it achieved the visibility goals we were looking for. But then we have to find signal on that downstream. So aided brand recall and aided brand recall in surveys. We have to look at the long tail of month over month and quarter over quarter growth in our self-service business. So we'll continue to hunt it down. It's our first major bet like this. And so I think it's okay to not be perfect at measuring to still feel good about the program. Yeah. And I know you were joking. I was not asking on behalf of the leadership team.

21:31I was asking on behalf of all CMOs and marketers who were thinking of doing something similar. You can help them kind of prepare, if you will, what to expect. And even we can even build on that, Melton. What are some lessons you would pass on to a brand who's thinking about doing something in a sports world. So the business case is so important. If you can sell the business case, you don't need to measure after the fact all that precisely, as long as you deliver what you said you would, right? And so a major sports marketing bet, this is a multi-million dollar bet. It's a multifaceted program.

22:04You have to get the entire business aligned to it, right? So it's not just a marketing activity and it's not uploading a logo file to a third party. So I think we had at its peak, I think we had 55 people in the business in our twice weekly standup meeting that was operationalizing across offers and pricing and packaging, our web experiences, the integrated content story, onsite hospitality, gifting, enablement of our sales organization, and then supporting them as they were using this as a lever to develop relationships with inside the customer race. in our new logo prospects, as well as our strategic partners and our distribution partners.

22:44And then wrapping that all in with a pretty sophisticated on-site hospitality program where we had more than 100 people come through a very well-orchestrated event experience from 5 in the morning until 11 at night on the longest day. And so it takes total company commitment. And so I would start there. If you're a marketing leader and you don't think you can get your CRO committed, then it's an uphill battle. I'm not sure I would do it. If you can't make it like it becomes a lightning strike moment. If you can't get the marketing organization, if you can't afford for the marketing organization to stop doing other things and do this, like this becomes the campaign.

23:28This is the message. This is the activation. This is in our case, the commercial. This is the digital program in this very short, condensed period of time where every message in the business is aligned. Then I wouldn't do it. If you can't get your CEO and founders to participate and be there with your customers and partners, then I wouldn't do it. And so you may sign the check at the end of the day, but you have to make this a corporate event, not a marketing event to be successful. It's a great point. It's all international. That's the first thing. I would go back. I mentioned before, you know, I think that being data driven is important, but knowing in advance that you're not going to be able to measure all of this, you need to be able to get everybody to collectively take the leap of faith.

24:11Yeah. And for someone like you, that's not easy, right? Being the data nerd. It's not right. Because the data will only take you so far. If it's the first program of its kind, you don't have muscle memory to fall back on. You don't have a model or track record or. There's no benchmark. Yeah. Yeah. And so you have to get comfortable with that. And then you have to sell it. Internally, this is something that you have to build excitement around and help people understand that this is strategic, not a boondoggle. And so you have to get dispassionate from it and become its top critic. If you're more critical of the bet than your most skeptical executive team member, if you're more critical of the execution or the internal alignment than the biggest doubter in the business, then you A, improve the quality of your execution.

25:00But B, you have the response when the inevitable, why are we doing this? This doesn't make sense. Objection comes up. You can quickly, you can have empathy. It's like, I thought of that too. Here's how I reflected on that. And then share like your perspective, which might be you're right in that aspect. But in the bigger picture, this is still worth it. Or it could be I don't agree. And here's like a different way to look at it. I want to I want to shift for a few minutes to your career path because it's fascinating. And my thinking is there may be others like who are where you were there now, right, to go from where you went, where you were to CMO.

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25:38But the path that you took is I said this to you off air. I've never been anybody who's taken the path you have to CMO from software development to product management to now running marketing. Spend a few minutes talking about how this came about, how this path came about. I'm telling you, Steve, that even listening to myself talk about justifying the sports marketing sponsorship seems so foreign. So I want to own up in advance. I'm very late in my career into marketing. We're talking about chapters earlier. This is my fourth act, probably. And so I'm grateful that I'm here. I found home after years of searching in my career.

26:17But I ended up... I backed into marketing almost grudgingly. I graduated college as an electrical engineer right as the internet became the internet. My first exposure to it was in my third year of college when we were able to network together a video game called Doom and run it on computers in different homes. It was so extraordinary. A lot of people just enjoyed the gaming experience. I started to ask the questions like, how is this even possible? And that led me down a path because a lot of an engineering program is software development. It led me down a path of searching for a career where I could build internet-based systems because that seemed to be important.

26:56I didn't know why, but it was very obviously more interesting than designing a modem chip, which is what my job offer was that I turned down in Silicon Valley, much of my parents. It's a huge disappointment. And so I went to work at a company that was just on the vanguard of building what today we would call a B2B software application. But again, there was no language for that back then. There was very first versions of web servers. There was the Mosaic browser. But they obviously had the bulletproof reliability of mainframes, which is what most business systems were in that era. But they had the usability of what at the time was called graphical user interfaces, GUIs, which were PC-based, Windows-based, usually, systems.

27:39And those graphical user interface systems had no scale. You could never roll it out to 100 people in an office or 1 ,000 people in a call center. But they were easy to use. Using a mainframe was unbelievably hard to learn. But the mainframe never crashed. And so my aha was we can build these reliable systems that are easy to use. This obviously is the future. I want to be a part of it. And so I talked my way into a software development organization. And it turned out I was a really poor software engineer. And I was very buggy. I was slow, but I made up for it by being low quality. And so I was quickly elevated out of a software coding role into being a project manager and interfacing with the customer on the requirements because it was a business system that these were being custom developed.

28:25And I wasn't all that diligent as a project manager. I couldn't run a project on time and things got a little squirrely. But I was really good working with the customer. And so I was promoted again just to get me out of harm's way. And so I became the account manager and scoped projects. And that was actually a lot of fun, problem solving. And I got good enough at that that they said, Hey, maybe you shouldn't do any contribution to the development because you're still an anchor on our boat. But we'd love for you to sell this for us because you really get it. And so I ended up into a long portion of my career where I was selling first custom software development.

29:04And then I came inside as a general manager of a smaller, what we call SaaS today, company as a general manager. And so in the general manager role, I had sales and marketing and professional services. But all of it was in service of truly understanding the customer's needs and making sure we delivered on that and kept them satisfied over a long period of time. A lot of my customer base was existing customers that I just continue to harvest expansion opportunities off of. And so that really taught me the appreciation of the product has to deliver. It's one thing to sell. But if you're selling promises that are never fulfilled, then you get to sell that customer one time and then they go away.

29:40Right. If you actually sell the solution to their problem, that solution becomes invaluable. It becomes core to their operation. and then it gives you permission to sell one more solution, solve one more problem and continue to add value because this is what I learned. It's like, it's actually a relationship that brings along software that is hired. Is this where the marketing side kind of opened up? It's not. So in that company, I was a little enthusiastic about the direction the product should go to satisfy these customers and was fortunate to be elevated to product officer and got to set product strategy in a brief period of time for this company.

30:21And then we were acquired. This was an expense reporting software. And we were acquired by Concur, which went on to become the industry giant in expense reporting. But at the time, it was a very level playing field with six or seven equal competitors. And they asked me to help them bring to market a free trial to buy basically a freemium version of their expense reporting product. At the time, they were purely enterprise. So I worked with a really talented set of people and helped build this free trial to buy a product and led from the product side of the house to go to market of it. And it was a total failure.

30:58It was unreal. We were so proud of it. But after six months in the market, it had$20 ,000 of monthly recurring revenue. The run rate, it wouldn't even pay the bill of two team members. Right. And we began to doubt it. Maybe there's not a market. Maybe people just want to continue to excel forms and save receipts to them. And so I became, again, a characteristic, I became a pretty vocal advocate for doing something different than we were doing. And that earned me a tap on the shoulder to step across and join the marketing organization, but lead marketing for this free trial to buy motion. And I went into that grudging line.

31:42No, no, you don't understand. I'm the product guy. This is not what I do. But I quickly fell in love with it. I had no idea how data-driven it was. When you could figure out where your buyers were, how to engage them, reach them, pull them in, bring them through a funnel. that buying experience, which for us was like coaching people through free trials. It really scratched the itch that had always been there in software development and sales. But the permission to do pretty outlandish things was too tantalizing to pass up. And so very early on, we just have to break through the noise. We have to be non-traditional with a lot of encouragement from the head of this group, a wonderful lady, Elena Donio.

32:20She gave us permission to go out and we did live read commercials with Howard Stern during a certain radio show where he would express his frustration as a small business owner. It's like, you know what I hate is when my employees don't get reimbursed and their spouse is like, hey, we have to pay a fee on our credit card bill because you can't get your money back. So he tapped into the empathy and then inside Concur, every phone would melt down. Our website would blip. Everything would come to a stop because everyone wanted the solution to that problem. And our poor front desk receptionist, She had no idea what was coming her way every 45 minutes when he did this commercial.

32:58And so we quickly learned that at scale, if you resonate with the problem that is haunting people, like keeping them up at night and is like truly feels like the unsolvable problem that has personal pain associated with it. If you can do that at scale, you're going to grow the business to the moon. And so not exclusive to that, but in marketing experiences like that, we outdistance all of the expense reporting competitors in that free trial to buy segment. And Concur went on to be a true juggernaut as one of the early SaaS pioneers. So those memories cemented for me is like marketing is the thing.

33:37I love it. What a great, hopefully that will inspire others who are in a similar position that you were, who are currently in that to go, So maybe there's something there when it comes to marketing. But if not, what a great time. I knew this time would fly by, my friend. I cannot thank you enough for spending a few minutes with me and my listeners. And I greatly appreciate it. Steve, it's been a real pleasure. Thanks for having me on. Well, that wraps up another episode of the CMO Whisperer Show. I hope you shared this episode with your friends. And if you have not already, please subscribe to be kept up to date on all the latest episodes.

34:08And if you're so inclined, leave me a review on your favorite podcast platform. Thank you.

From the publisher

My guest today is Melton Littlepage, CMO of 1Password—trusted by more than 100,000 businesses to protect their data. 1Password gives you complete control over passwords and other sensitive business information. 

Melton has a 20-plus-year track record of innovation, category creation, and growth acceleration at technology companies. Prior to joining 1Password, he was the CMO of Outreach—the leading sales execution platform—helping individual sales reps and entire revenue organizations create more pipelines and close more deals. 

At Outreach, Melton led global teams responsible for strategic communications, brand, demand generation, customer expansion, product marketing, community, and sales development. 

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