August 24, 2023

Strategic Marketing Collaboration: Find your partner in crime (podcast episode #68)


Colleen O’Brien, Chief Communications Officer and Head of Strategy, Armoire, shared her insights and experience in episode #68 of the How I Made It In Marketing podcast.

Listen now to hear O’Brien discuss Microsoft's Venture Fund rebranding to M12, the importance of conviction in a single approach, the value of finding complementary partnerships, and more.

by Daniel Burstein, Senior Director, Content & Marketing, MarketingSherpa and MECLABS Institute

Strategic Marketing Collaboration: Find your partner in crime (podcast episode #68)


Join us in the AI Guild. Chat with MECLABS AI to learn more – (MECLABS is the parent organization of MarketingSherpa)

We all know that if we run a marketing experiment, we can get a loss.

But here’s a topic that is discussed less often.

Sometimes you just didn’t get that win…yet. You need to make sure to let your test run its course.

Or as this episode’s guest describes it in her podcast guest application, “Everything is expensive until it starts working.”

Here to share the story behind that lesson, along with many more lesson-filled stories, is Colleen O’Brien, Chief Communications Officer and Head of Strategy, Armoire.

Armoire has raised $13 million in funding so far, and investors include Microsoft CEO Satya Nadella. Its customer base has grown more than 100% year over year.

Over the past year, O’Brien has earned 15 top-tier press mentions for Armoire, including The New York Times, The Wall Street Journal, Condé Nast Traveler (and now, the How I Made It In Marketing podcast).

Listen to our conversation using this embedded player or click through to your preferred audio streaming service using the links below it.

Listen on Apple Podcasts | Listen on Spotify | Listen on Google Podcasts

Stories (with lessons) about what she made in marketing

Some lessons from O’Brien that emerged in our discussion:

Brand affinity isn’t static

This lesson probably feels obvious. But here’s what made it real for O’Brien: When Microsoft Ventures launched in January 2016, Microsoft didn’t have a strong reputation in Silicon Valley, where they expected to do a lot of their business. Two years later, the company’s venture fund rebranded to M12 to help investors get their foot in the door.

When brand perception for Microsoft began to improve under Satya Nadella’s leadership, the conversation opened again: is there opportunity in better aligning to the parent company? Should we revisit Microsoft Ventures?

Her lesson learned: When diverging from a branded house, it’s critical to weigh the tradeoffs between short-term business gains and long-term opportunity. M12 perhaps benefitted from short-term distance from the tech parent but won’t reap as much of the halo effect benefit that “Microsoft Ventures” might see in today’s generative AI environment.

Do something right, once

On the product marketing team, O’Brien was responsible for building their presales website. was a lead generator for Microsoft’s Office business, so they had a formidable budget to collaborate with great creative agencies. The early proposal that she shared with her marketing director showcased three different ways to navigate the site—a standard scroll, button clicking on stacked content modules, and a persistent vertical side bar navigation.

His response: let’s do something right, once. In other words, let’s have strong conviction in one approach, and throw all of our weight behind that thing. While this feels like a very small anecdote, it helped her develop a sniff test for a peanut buttered strategy. Especially when we have a point of view, let’s bet big—not hedge our bets, she says.

Find your partner in crime.

This isn’t advice to find your “work husband” or “work wife.” Instead, this was a humbling challenge to understand her shortcomings as a business leader, find someone who had a complementary skill set, and figure out what O’Brien could barter for their brain.

When Windows 10 launched, they were in a new era of “Windows as a Service.” They had real-time data to assess customer behavior in the product for the first time. She had a little bit of experience thinking about services at scale with, and enough exposure to Excel modeling through her business school classes to know that it wasn’t her strength. She found Ricky Johnston, who was a Senior Data Scientist at the time.

O’Brien traded him business insights for his analysis expertise – across org siloes. Their main collaboration became a project of major interest in the Microsoft Marketing organization as Johnston mapped the universe of Windows customers for personalized lifecycle marketing journeys. The visibility with executives and ingenuity to cross org structures was widely lauded and resulted in career acceleration for both of them.

Lessons (with stories) from people she collaborated with

O’Brien also shared lessons she learned from the people she collaborated with.

Give people something to react to

via Bonnie McCracken, Director of Innovation and CEO Communications at Microsoft

O’Brien worked with McCracken on the Product Marketing team at Microsoft. The meetings that she ran were always very efficient and effective because instead of prompting a discussion with just a problem statement, McCracken would also have a proposal for how to move forward. It showed O’Brien that one of the best ways to get folks to articulate their points of view is to put content in front of them (instead of waiting for them to come up with the solution).

This strategy gets people on the same page more quickly – dialing in a solution vs. trying to stitch together totally divergent jumping off points. It also creates a strong sense of urgency – “if you don’t tell me your opinion, this is what I’m going to do.”

Go back to the brief

via Dawn Martynuik, Senior Manager, Alexa on Fire TV at Amazon

Martynuik led the marketing team, and she was the best marketer O’Brien ever worked for! Even in a fast-moving, growth hacking environment, Martynuik cultivated a very rigorous marketing culture and required briefs for every project. As a young marketer, O’Brien quickly learned how to ground in business objectives and memorialize all of the background information in a business challenge or opportunity.

She proactively created measurement plans for every campaign they pushed out as a team. Martynuik was a fountain of knowledge and experience, but she also fostered individual confidence and accountability. If scope creep ever reared its ugly head, Martynuik had a strong directive: “go back to the brief.”

Everything is expensive until it starts working

via Kristin Marchese, Chief Marketing Officer, Armoire

A test-and-learn mentality is part of Marchese’s team’s approach to growth. In addition to funding tried-and-true marketing channels, they always set aside budget to experiment on new channels. When O’Brien first started at Armoire, she was working on some of these emerging opportunities, or channels that were just relatively new to them as a business—like podcast advertising. Early on, when she looked at the comparative customer acquisition costs, she wanted to turn off their experiments quickly—gah, everything is too expensive!

Marchese coached her through this knee-jerk reaction. Everything is expensive until it starts working. Figuring out something new is costly—both when it comes to time and money. But if you can stomach those upfront costs, and work to understand how something may or may not work, the truer opportunity will become clear as you learn the ropes.

Related content discussed in this episode

What is Data? A discussion about getting value from your marketing analytics

Creative Marketing: Does it all make sense? (Podcast Episode #19)

About this podcast

This podcast is not about marketing – it is about the marketer. It draws its inspiration from the Flint McGlaughlin quote, “The key to transformative marketing is a transformed marketer” from the Become a Marketer-Philosopher: Create and optimize high-converting webpages free digital marketing course.

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Not ready for a listen yet? Interested in searching the conversation? No problem. Below is a rough transcript of our discussion.

Colleen O'Brien: Part of the attraction of bringing folks who have had big company experience to the startup environment is how can they bring some of the efficiencies or some of the structures that that have been built into their career to date to this growing startup? But it is a balance, as you've mentioned, like I want to avoid bringing too much overhead to this fast, fast paced, fast moving startup.

And I guess something that I would say, is it enmeshed in the Microsoft world? The creation of a brief would take days, weeks to figure out, like our point of view, our strong conviction around a strategy. And today, sometimes I have to write a brief in 15 minutes before we decide whether or not we're going to do something.

Intro: Welcome to How I Made It in Marketing from Marketing Sherpa. We scour pitches from hundreds of creative leaders and uncover specific examples, not just trending ideas or buzzword laden schmaltz, real world examples to help you transform yourself as a marketer. Now here's your host, the senior director of content and marketing at Marketing Sherpa Daniel Burstein, to tell you about today's guest.

Daniel Burstein: He's been we all know that if we run a marketing experiment, we can get a loss. But here is a topic that is discussed less often. Sometimes you just didn't get that win yet. You need to make sure to let your test run its course. Or, as my next guest describes in her podcast guest application, everything is expensive until it starts working.

Here to share the story behind that lesson, along with many more lesson filled stories, is Colleen O'Brien, the chief communications officer and head of strategy for Armoire. Thanks for joining us, Colleen.

Colleen O'Brien: Daniel, thanks so much for having me.

Daniel Burstein: So always like looking at our guests education, it is so rarely in marketing itself for you. You majored in film production in Harvard, which you got a chance to learn both the creative side and the physical production side. Then you went to work on it. You went to work at Microsoft for 11 years and working up to the executive communications lead to be executive vice president of Microsoft.

As you're you're also chief marketing officer for M12, which is Microsoft's venture fund. And you are now chief communications officer and head of strategy for armoire. As I mentioned or more, has raised $13 million in funding so far. And investors include Microsoft CEO Satya Nadella. The customer base has grown 100% year over year, more than 100% year over year.

And asking O'Brien one of her top accomplishments, you mentioned that with all her pitching she's done in the past year, she does not have a PR agency. She's rolled up our sleeves. No vendor. She's doing it herself. And she has earned 15 top tier press mentions, including Wall Street Journal, New York Times, Condé Nast Traveler, and now the How I Made It in Marketing podcast.

Well done, Colleen. So give us a sense, what is your day like as chief communications officer and head of strategy at Armoire?

Colleen O'Brien: Absolutely. And thank you for the wonderful intro. That was lovely. Armoire is the clothing rental membership that helps ambitious women love what they're wearing and the way that I think about my role there on a daily basis is really split up into three buckets. So the first bucket, when I get in, I open my computer, I get my cup of coffee in the morning, really thinking about earned media.

And as you said, we're not working with a PR firm right now. So I come at this from a news jacking perspective. I start with press monitor monitoring in the morning and then figure out where can I insert armoire into the conversation, what's going on in the world, and how can armoire be a part of it today? So I do this largely through newsletter consumption and focused on fashion trade publications, on start up tech and entrepreneurship media, on women focused media.

And then I do a lot of quick writing and pitching to start the day. The next big bucket of my day. I'm thinking a lot about lifecycle marketing. We are hyper focused right now on churn mitigation and I think about the strategy and writing up of our lifecycle marketing to, you know, help our customers get through this paradigm shift from buying clothes to renting clothes.

And then for the back third part of the day, I put on my strategy hat. I manage our rhythm of the business. I partner with functional leads from operations to merchandizing to our tech and product team, and I partner with them on writing white papers and long term plans. And I manage our investor relations and work with our advisory board as well.

Daniel Burstein: And I do want to mention this isn't the red carpet. We don't normally ask what what are you wearing? But what are you wearing today?

Colleen O'Brien: Calling for color. Danielle, Thank you for asking. I am wearing a power blazer from Wild Fang, which is one of the most beloved brands in our Mars inventory.

Daniel Burstein: Very nice. I also want to ask you about the press mentioned. So armoire, that's a brand that is also a generic term. And I wonder if you've come up with any tips or hacks to be able to monitor that effectively. And like, for example, one of our brands is marketing experiments. Great name, right? Great for search and SEO and stuff.

But when you get the press mentions and some of these things, well, you know, a lot of general terms get pulled in. So have you any tips or hacks to to sort the wheat from the chaff for more?

Colleen O'Brien: That is a great point. And part of the reason why we are not owners of our Morcombe today, it is a category in furniture that is could likely lead to really great lead generation for some furniture store someday. But we do a lot of we do a lot of proactive monitoring of joint keywords like armoire and clothing rental armoire, and the name of our founder and CEO, Ambika Singh.

And make sure we have all of those coupled terms together to make sure that we're capturing the right press mentions.

Daniel Burstein: Smart idea. Well, let's jump into some lessons from the things you made in marketing off and say this is one of the cool thing about being a marketer. We get to make things right. I've never done any other profession. I've never been like a podiatrist or an actuary, but I don't feel like everyone leaves their job and say, I made that thing.

But we make things like, You're making me more brand right now. So here's one of your first lessons. Brand affinity isn't static. Tell us how you learned this lesson.

Colleen O'Brien: Yeah, this was a hard lesson to learn. I learned this while working at Microsoft on 12, which is Microsoft's venture fund. We were investing in B2B software as a service companies and micros ventures, as it was originally called, launched in 2016, at a time when Microsoft didn't really have a strong brand reputation in Silicon Valley, especially Silicon Valley, of course, was really marked by these prominent brands like Apple and Google had incredible startup culture, and Microsoft wasn't really part of the conversation at that time.

So folks working for Microsoft Ventures flagged like, I'm having trouble getting in the door. I can't get people to accept my meetings. We don't have the right brand affinity for this target audience. So two years later, in 2018, Microsoft Ventures decided to rebrand to M12. And that rebrand did help them get in the door. They distanced themselves a little bit from the parent company in order to land those meetings, in order to meet with the top entrepreneurs.

Then Satya Nadella assumed leadership as CEO of Microsoft and the tide started to turn like people were interested in Microsoft again, there was this notion of growth mindset of being customer first. We launched a ton of great products that became beloved in the market, and people were interested in Microsoft again. But by that time, 12 had sort of distanced themselves from the parent company and couldn't really, you know, take advantage of that halo effect.

So my lesson learned there is like really think about the long term opportunity when it comes to brand affinity. And if there is if you are in a branded house, even if there are, there are some short term pain. Is it worth enduring for a longer term bet?

Daniel Burstein: Yes. So when you make a decision like that or any brand decision, like what role does data play for you? What role has data played for you? Because, for example, when we benchmark marketers, we ask them what they use instead of analytics to make decisions. 42% relied on gut instincts, and 33% said some type of official brand awareness data.

So to me, this sounds like one of those gut instinct decisions around branding or just hearing from kind of a salesforce of business development for us. But maybe I'm wrong because I know also, you know, Silicon Valley culture, it's data driven, right? Everyone's making data driven decisions. So, you know, for you, what role does data play in brand decisions?

Is it the gut or are you turning to some specific data?

Colleen O'Brien: You know, I think that the data that was apparent at the time was really we're not getting meetings like I wish that I could tell you. Oh, I we leaned on search engine data to see what people were searching for it, to sort of indicate where we should go with our brand. Or we did a massive customer brand perception survey to figure out where we should go, but those were all like, nice to have data points versus the business reality that, you know, these investors couldn't get in the door to the people they wanted to meet and that was that.

But any other data that we could have been looking at at the time.

Daniel Burstein: That makes sense for us. Let's take a look at another lesson from your time at Microsoft. You said do something right once. What do you mean by that?

Colleen O'Brien: Yeah, another. Another. I mostly wrote up some tough lessons here.

Daniel Burstein: Those are the best ones.

Colleen O'Brien: Yeah. Yeah, I guess so. Trial by fire. So I learned this lesson on the product marketing team. I'll sort of ground you at the point in time. We were rebranding from Hotmail to, and the company was thinking about this product as a lead generator for what was at the time the Office 365 business. So there was a significant budget to think about how do we make this thing work, which allowed us to work with some like incredible creative and strategic marketing agencies.

I personally was responsible for our pre-sales site, our pre-sales website, and I was working with this great creative agency and got some early marks back for what we could expect, what our website was eventually going to look like. And I brought some of them to my marketing director at the time, and he pointed out that there were like no fewer than three different ways to navigate this site.

And maybe that sounds like a win for the customer. Like whatever they want to be doing, they can click around and get to where they want to go. But what he made clear to me was that we were sort of like introducing a lot of complication and we're showing up as if we didn't have a strong point of view on what we wanted folks to do when they landed at that website.

You know, there was this standard scroll thing going on. There was button clicking among all of these stacked content modules, and then there was a sidebar navigation as well. And his reaction, his feedback to me was like, Colin, let's do something right once instead of like throwing a bunch of different things out there and like seeing what sticks.

Of course, like that is a lesson for a different problem. Sometimes you do want to throw a bunch of stuff out there and see what sticks. But the challenge to me, and like what I took away from this was when I can develop a strong point of view and I have some gut conviction about something like That's the thing we should throw our weight behind.

Daniel Burstein: Now I hear you agree, and especially about guiding the customer's thinking, but it's something you said in there when I kind of more dove into about working with a great creative agency. So when you are working with a creative agency, how much do you dictate to them? Like you said about the customer experience versus how much do you give them free rein?

So, for example, I interviewed Carlo Carbone, the global chief creative officer and partner at 72 and Sunny on How I Made It Marketing Podcast. One of his lessons was if your client is not as ambitious as you are, you're not going to do anything great. So that's from the client side. But now that's from the agency side. But now I've got you on the client side, on the brand side.

So when you've worked with creative agencies, how much do you dictate versus how much do you just give up blue sky? Or are there different situations where you do both?

Colleen O'Brien: I think about my role in our relationship with the creative agency as the business owner. Like my job is to write a really strong brief that provides creative minds with all of the background that they need on this problem. But also, like what I am trying to drive, what is my business objective? What is the measurement plan that I'm going to assign to this project?

I don't like to get too prescriptive when it comes to creativity because that's what they are best in class up. That's like why we've we've structured this contract in the first place. But reigning in the creativity to make sure it is aligned to the business objective, to make sure that it keeps our measurement planned in mind. Like that is my role in that relationship.

Daniel Burstein: Okay, great. And speaking of relationships, another one of your lessons is find your partner in crime. I think you need more internally in an organization. So how have you found your partner in crime?

Colleen O'Brien: Yeah, and maybe this feels like a little bit more relevant in a large company like Microsoft, for example. But I do want to be clear that this is not advice to find your work husband or work wife or like someone you love to rant with. At the end of the day. This was like really a lesson for me and self-awareness and understanding the limits of my skill set, figuring out like what I was really good at and where I had some major gaps in my knowledge and skills and abilities and the person who I found.

Richard Johnston, he was a senior data scientist at the time working on Windows was someone who like really helped me figure out how to get to the next level in my career. And this relationship was mutually beneficial. So I would sort of trade him business insights or here's what I heard in this meeting. And he could come back and say, Well, here is what we're talking about in a parallel organization.

It was a way for us to structure across silos and, you know, make two plus two equals five. So the visibility with executives that we were able to achieve because of this cross silo relationship and projects that we were able to execute it like really helped us accelerate both of our careers because we were covering those skill gaps.

Daniel Burstein: How did you find Richard? Because, you know, when I've had the opportunity to work in large organizations, you know, one of the things about being successful, large organization is just being able to navigate it. And when I've had those good relationships, it just kind of came down to serendipity. And sometimes you don't realize, like all the things that are going on in an organization that you can leverage or all of the possible, you know, solutions that you can use just because it's like such a big organization.

So was it serendipity or was there any, like, tactical way you approached it to say, okay, I have this skills gap? You know, I've I've taken a skills test or whatever, right? I've got this skills gap. And let me look at the organization and boom, they feel that skill and I'm going to recruit that person. I've got these three people and who am I going to recruit?

Who am I going to bring in? So what was there anything like, anything you learned from it? Or was it just serendipity, like you bumped into him in the cafeteria and and it was a match made in heaven.

Colleen O'Brien: So at the time I was going to school nights and weekends to get my MBA at the University of Washington here in Seattle and I was learning about regression lines and using Excel. So I just like had this sort of self-awareness or awareness of like what was possible and self-awareness that like I was not great at this thing.

I think that coupled with my curiosity about like the organization, more holistically and all, like make this a little bit real or I would like spend time looking at the org chart like what is the structure of the company? And like, how do I fit into this larger picture? And that's what helped me realize like, oh, there is a whole team dedicated to thinking about data analysis and business intelligence and like, I'm just starting to understand the vocabulary of that field, but there's a lot for me to learn there.

And wouldn't you know, Ricky, when I looked him up, was just a couple of seats away on the same floor as me in this building. But I would say that, like spending time with the org chart and like figuring out where I fit in was super helpful for me.

Daniel Burstein: That's great. The other thing I like about that is if you've ever learned John Maxwell's 21 laws of leadership, one of his laws is people don't pay for average. So basically, if you have some sort of gap in your skills, like don't work really hard to get an average work on your best skills, make them the best possible and find someone you can team with.

On those skills you're not so great, so stare at the org chart with the org chart, you know, dream of your work chart. Maybe you'll you'll find someone. So the first half of the podcast, we talk about lessons we learn from things we made marketing in the second half, we talk about lessons we learn from the people we collaborated with, because those are the two great things we get to do as marketers.

We get to make things and we get to make them with people. But before we get there, I should mention that the how I made it in marketing podcast is underwritten by OBS Institute, the parent organization of Marketing Sherpa. You can join the MC Labs API Guild to discover a path to the Artificial Intelligence Revolution. Learn more by chatting with Mac Labs II at Mech Labs, slash A.I. That's messy lab slash a AI.

All right. Let's talk about a lesson you learned from someone you collaborated with. That person is Bonnie McCracken, the director of innovation and CEO communications at Microsoft. And you learn from Bonnie to give people something to react to. So what you mean by that?

Colleen O'Brien: Yeah. So Bonnie was an incredible colleague of mine early on in my marketing career. We worked together on the product marketing team at Microsoft, and I just noticed something about Bonnie early on that felt very different from other folks I was working with. When we would go into a meeting that she was leading, it just seemed more focused, more efficient, and we would leave the room, like with a plan.

And that wasn't always the case when I was in meetings, depending on who was leading them on my team and I tried to hone in on like, okay, what is Bonnie doing differently that is making this process work is like pushing the business forward every day, like we are making iterative progress. And her background was in PR, she was a communications leader, and she would come to every meeting with something for people to react to.

So like that is the major lesson that she has taught me is like give people something to react to. Of course there is like a time and place for brainstorming and starting with the problem and diverging before you converge. But what Bonnie showed me, especially if, like you have a fast timeline, you need to like make moves sooner rather than later.

Giving people something to react to is a great strategy for like dialing in a solution versus like, you know, sticking together, totally divergent, jumping off points, coming from different sides of the room. It also creates this like really strong sense of urgency for people because they see like if they don't dove in and offer a point of view or point you in the right direction, like, well, if I don't give you my opinion, like I see exactly what you're going to do.

So, yeah, it creates this sense of urgency as well.

Daniel Burstein: Yes, that's great in marketing in PR. But let me ask you, you've also worked in executive communications. I wonder if you've used this tactic, because for me, earlier in my career, I worked in executive communications and I was fairly young working with high level leaders, and I would have to do things for them, like write blog posts or letters or make presentations, right?

And it was very hard to get their time and actually get something from them. And what I found, like you said, is I would have to give them something to react to. Like I would come up with whatever the presentation was or Barbara. And then that really made a more productive meeting where they're like, okay, boom, boom, boom, not this, it's that.

And it really kind of helped, you know, hone in their thinking. They were so busy versus showing up to that meeting with nothing, getting that limited amount of time with them being like so what should this presentation be about? You like 10,000 people next week, you know, so have you have you used that tactic in executive comms as well?

Colleen O'Brien: Absolutely. I have written on topics that I know nothing about. Yeah. Quantum computing to like AI at scale. There are so many topics where I am not an expert, but my time with the expert is fairly limited. So doing some quick internet research, figuring out like what is an interesting point of view, and then pressure testing that with the executive, you know, who's going to say the thing out loud?

That was a much more efficient strategy in executive communications than, you know, getting those 5 minutes with them and trying to stitch together something from their frazzled brain.

Daniel Burstein: Yeah. And I imagine now you've mentioned Jenner generative AI a bit, I think toward the end of your time at Microsoft and a lot of that stuff really blow for Microsoft and I tend to delegate all that. But I would think to folks could probably use generative AI today even if they know absolutely nothing to at least get that ball rolling and have something to present.

Obviously, do not say it's your own work. You know, be clear what it is, but I think that could be a game. Have you played with that at all in terms of anything we've talked about?

Colleen O'Brien: Yeah, absolutely. Like coming up with something for people to react to is way easier now than it ever was before. It is now something that like is not just my job because my head of ops can also type into chat about what like what my armoire is point of view be on this topic that's trending in the media right now.

Anyone can sort of like come up with a jumping off point to have a productive conversation with some of these generative AI tools.

Daniel Burstein: Yeah. So now none of these great ideas matter if we can't get anything done right, if we can't execute. One of your lessons is go back to the brief. This was from Don Martine, Newark, senior manager of Alexa and Fire TV at Amazon. So how did you learn this from Don?

Colleen O'Brien: So Don led the marketing team and she was far and beyond like the best marketer I ever worked for. And, you know, even in this fast paced growth hacking environment, when we were rebranding Hotmail to, she cultivated this like very rigorous marketing culture and required briefs for every project, sometimes like opportunistic things would come up and she would still say, like, let's like take a beat and make sure we understand that their business objective, we understand what we're trying to do.

We have a point of view on the strategy and there's like a firm measurement plan in place. And as a young marketer, that rigor was just instilled in me and to this day, when folks will come to me and say, Hey, this is a quick, opportunistic partnership, should we do it? I will take a beat to figure out what is the brief that might lead us to do this thing.

And when we're a couple of weeks into the initiative, how do we make sure that it's still a good use of time? I will like go back to the brief and remind myself, what were we trying to do? And like are we making any progress to get there? So if scope creep is happening or we're drifting a little bit from the original business objective, going back to the brief helps me re ground in what is the important work right now.

Daniel Burstein: So you came from Microsoft, which is a company of 100,000 massive company moving to a much smaller company now is a career progression. Obviously that happens often and I wonder what types of processes you've kept and what type of processes you've thrown to the side. I'll just give you one example. When you mentioned marketing brief, something that I see that gets overlooked so often is actual value proposition, right?

Not only what is the overall value proposition of the company, but what is the value proposition of this initiative we're talking about? Right? If we're going to build an app, if we're going to build an AI tool, if we're going to roll out a new product offer, like is there really value for the customer versus is this just some, you know, internal initiative we want, for whatever reason, to get slightly better margin and impress our investors.

Right. So, you know, for you, shifting from massive Microsoft to, you know, more of a startup environment now, what processes are you like, yeah, this we're holding on to this and what others are like, Oh man, get that out of my way. I can get things done quicker this time.

Colleen O'Brien: Yeah, it is a, it's a great call out and I think like part of the attraction of bringing folks who have had big company experience to the startup environment is how can they bring some of the efficiencies or some of the structures that that have been built into their career to date to this growing startup? But it is a balance, as you've mentioned, like I want to avoid bringing too much overhead to this fast, fast pace, fast moving startup.

And I guess like something that I will say is in the in the Microsoft world, the creation of a brief would take days, weeks to figure out, like our point of view, our strong conviction around a strategy. And today, sometimes I have to write a brief in 15 minutes before we decide whether or not we're going to do something to like quickly dove and figure out what's the background data?

Do we have any historical like similar projects that we've done like this in the past that we can learn from? Okay, go or no go? So I would say like the timeframes affiliated with the processes are just much shorter.

Daniel Burstein: But it sounds like you're still, you're still doing that free. Even if you're doing a shorter brief, you haven't thrown it out the window.

Colleen O'Brien: That is correct. I am like always going back to the brief so that that lesson is very much instilled in me and I think is like important marketing rigor.

Daniel Burstein: Yeah. Now you I, I saw this picture of you. You had this very clever mug. Were you involved in the creation of that mug?

Colleen O'Brien: I wasn't it it predated my time at armoire and I think I know what you're talking about. It is a mere mug. Mirror is a great company here in Seattle. Am I r? And the mug says these aren't my pants. Are we on the same page?

Daniel Burstein: Yeah, I love it because I thought that was a perfect example of I could see nothing against Microsoft. A company of Microsoft size will say something like that would be very difficult to get out the door. And I see you holding that one of your bio pictures. I'm like, that is a great example of startup culture where it's like, Hey, this line perfectly exemplifies what we offer.

The value proposition our customers as print out mugs. Let's get it out there.

Colleen O'Brien: Yeah, these are my pants. Mug is one of the I think one of the best merch items that we have, one of the most beloved pieces that we sell to customers. And that copy was written by our CEO. And at the time, even internally, it was like a little bit contentious. Not everyone loved the line, but it like very it perfectly encapsulates this experience of clothing rental when were like out in the world wearing something that you don't own.

Maybe it feels like a little bit outside of your comfort zone. You have like a little bit of a secret and in a cheeky way sharing with people like, Oh, I don't own this item of clothing. It's sort of like a it it is a fun side effect of clothing rental as a behavior.

Daniel Burstein: I'm a writer. I love a good line, but it gets into this next topic of marketing experimentation, of trying things out. Your lesson. As I mentioned the beginning, everything is expensive until it starts working. You learn this from Kristen Marchese, the chief marketing officer of Armoire and take us through like what were you testing at the time that that Kristen taught you this?

Colleen O'Brien: So we were actually testing podcast ads at the time, ironically, and we saw that we weren't getting, you know, the same conversion rates that we saw in some of our tried and true channels. And with a startup mindset and like being so conscious of spend and where our dollars are going. I like very quickly wanted to shut things down.

I said to Kristen, like our customer acquisition costs are getting out of control. Like this channel is not performant. We need to stop this before this gets out of control. And her point of view was like, okay, let's take a beat. I hear where you're coming from. This is something that should dictate where our limited resources are going, but everything is expensive until it starts working once.

If and when this starts working for us, it might not be expensive. It might be like a very efficient way for us to grow our customer base. But right now we don't have the knowledge that we need about, you know, who are the right podcasting partners, what is the right messaging for that audience. We don't have the strategy in place.

We need to figure out what that is to execute more efficiently. But like, let's test and learn and take a beat because it might start working.

Daniel Burstein: Our way far enough down the journey. If we've we've tested learned enough, do we know if the story's turned around? Has it taken a happy turn?

Colleen O'Brien: It has taken a happy turn. We have had several successful podcast partnerships and also like have a strong point of view on the components of that partnership that make it work for us.

Daniel Burstein: What are some of those components?

Colleen O'Brien: So being in clothing rental, as you might imagine, a visual component is really complementary to the on air audio. So building into our podcast partnerships, some Instagram posting or some visual posting on behalf of the the hosts of the show has been like the unlock for us. Even if they're giving a strong endorsement over the air, audiences want to see what the clothes look like on that individual too.

Like for it to be a more authentic message.

Daniel Burstein: That makes sense. It brings up, you know, we had a lesson we I mentioned we have this Mac website guild and we have these weekly meetings and we're talking about an email marketing campaign we did for a nonprofit that also sells goods. And you mentioned typically we say we don't want to sell an email, we want to sell on the landing pages, get people to click through in email.

So on the landing page. But we've taught that, taught that, thought that. And then when I showed this example, what I did was I sold an email because the website was so bad, we now have time to change it. We had to sell the email. So brings up a great thing you're mentioning where there could be a best practice out there and someone could be like, Oh, you know, audio podcasts are the best and you don't need anything else.

But yeah, that might work for a lot of brands, that might work for a B2B software, might work for a mug or something else, but you know, best for your brand. Well, it's a very visual brand. You better put some visuals out there. So I think that's a great example of not just following a certain best practice. So we talked about a lot of different things about what it means to be a marketer.

If you had to break it down, what are the key qualities of an effective marketer?

Colleen O'Brien: I think that the key qualities that have helped me as an effective marketer and that I think are like relatively universal, are number one to be a great simplify or to constantly be thinking about like what are the things that we can pull out of the customer journey, of the customer communications to like make this golden path to success more apparent?

How do we like get out of their way with the things that don't matter enough? So being like a very rigorous amplifier has been important in my career. And then the second thing that I will say is constantly thinking about my writing skills and improving my writing skills and like practicing writing every day. Pitching is part of that.

Thinking about our life cycle, customer communications is part of that. Learning best practices for writing, writing across different channels. That has made me a more effective marketer, and I think the marketers around me who invest in that skill are the people who I most like to work with.

Daniel Burstein: I'm glad you mentioned writing because with generative AI a lot of us think, Oh, we can just outsource it to I know, just have I write everything and I use A.I. too. I love it. But to me, writing is thinking, right? Writing is just like writing a thing. When you sit down to write, you think after you work through the problems, work through your brand.

So I love that line so well, love all of us today. So thank you so much for joining us.

Colleen O'Brien: Yeah, thanks so much, Daniel. This was such a great conversation and I really appreciate the opportunity.

Daniel Burstein: And thanks to everyone for listening.

Outro: Thank you for joining us for how I Made It in marketing with Daniel Bernstein. Now that you've gotten inspiration for transforming yourself as a marketer, get some ideas for your next marketing campaign from Marketing Sherpas Extensive library of free case studies at Marketing Sherpa dot com that's marketing SRH ERP, Ecom and.

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