Transcript: Balancing Quick Wins & Long-Term Planning At a High-Growth Startup with Tiffany Keel

On this episode, I was joined by Tiffany Keel, Head of Customer Advocacy at ClickUp. Prior to ClickUp, she ran customer marketing at companies like ON24 and Nextiva. When she started at ClickUp, they’d grown tremendously through product led growth, but were still early when it came to the types of programs you typically think of in B2B marketing. She shares how to hit the ground running in a fast paced startup, why you need to mix quick wins with foundational planning in your first few months, how she secured hundreds of people for their reference program in only a few weeks and partnering with customers to create long-term plays to showcase them far into the future. Without further ado, here’s my conversation with Tiffany. 

Margot Leong: Hey Tiffany, welcome to Beating the Drum. I’m really excited to hear a bit more about what we’ve got going on with your time at ClickUp. Can you tell me about your background and sort of your journey into customer marketing? 

Tiffany Keel: Yeah, absolutely Margot, and first of all, thanks for having me on Beating The Drum. Excited to be here. I currently head up customer advocacy at ClickUp. But I actually started my career in sales, shifted into event marketing, which is where I really saw a big opportunity for customer marketing. You know, being boots on the ground in the field. I was talking to so many happy customers and I realized there was a big opportunity to harness all that happiness and drive that back into the business. 

So that’s ultimately how I got into customer marketing and now I’ve been doing that, gosh, I don’t know even how many years now. It feels like forever. When you love it, you know? 

Margot Leong: Being in the field, there’s a lot of the exposure that you can get to those happy customers, to customers in general, that actually is a really nice jumping off point for being like, I’d love to just talk to customers all the time, you know? Customer marketing is a really good landing spot for that. 

Tiffany Keel: 100%. 

Margot Leong: What are the things that you enjoy the most about customer marketing? Why do you sort of keep focusing on this area? Why do you keep coming back to it? 

Tiffany Keel: I love talking to customers and learning from our customers. I love talking to people and hearing not only their work stories, right? But their personal stories and it’s just so interesting to me. I like to see my role and I think a lot of customer marketers probably see their role this way is you’re almost this mini sports agent, right? You are understanding your customer’s strengths and you’re trying to find the right opportunities for them.

And honestly, nothing makes me happier than to see a customer really grow in their role and career. I love being a part of that journey. It really is fulfilling for me and why I’m even in customer marketing. 

Margot Leong: Prior to ClickUp, you were at ON24. That’s where you and I had touched paths if only briefly. I think it was an Influitive meetup. 

Tiffany Keel: Yes, it was like a dinner. 

Margot Leong: Yes, exactly. I mean, it feels like forever ago. 

Tiffany Keel: I think it might have been seven plus years ago or something long, a long time ago. 

Craziness. And then our one of my other friends, Emma, who’s at Twilio now, like she was, I think there too. It’s just, and we’re all still in customer marketing. It’s just crazy how time flies. And how small the world is and the community is too

Margot Leong: And Jane Menyo, who I know was your manager over at ON24, I interviewed her for the podcast as well. She’s absolutely incredible. I think she was raving about all the great work that you did with the webinerds and getting that whole advocacy community going. 

When you joined ClickUp, if you could set the scene, what did it look like when you joined? Was there already advocacy motions in place? Was it pretty greenfield? Give me a sense of what that looked like. 

Tiffany Keel: When I started a year ago, there really wasn’t much. Totally just open opportunity. We didn’t have really any of the traditional programs you would normally think of in a B2B marketing space. We didn’t have case studies, we didn’t have a reference program. We didn’t have any of those kind of basic foundational programs you would think about. It has to do a lot with how ClickUp has grown. 

Total PLG company, right? So a lot of just focus on acquiring new users. There just wasn’t a big focus on the B2B arm, more focus on B2C. And so with this shift and us moving up obviously needed some more of these key programs, especially for our growing sales team. 

But for me, what really drew me to ClickUp a year ago was you can just go to LinkedIn or Twitter and there already are so many passionate users of our product and I knew with just a little bit more energy and me coming in, there’s just so much impact I could make on the business. And it really was building everything from the ground up was the start of the play when I joined ClickUp because there was nothing.

Margot Leong: You know, I think that’s a really good point, right, is even when you are evaluating opportunities to do customer advocacy at future companies, that is actually something I also look for, right? Is the passion already there for the product? Does the product naturally engender love? 

But my understanding is click up is a project management solution. Did I have that right? 

Tiffany Keel: Yes. Spot on. Spot on. Of course, our marketing pitch is more about all in one productivity platform. But yeah, like totally in the project management space. And so yeah, we have a wide market to go after, right? Because really anybody can tap into the power of project management, which is also exciting for me because being at ON24, what was exciting about doing customer marketing there, was we were marketing to marketers, which, how fun is that? Like marketing to your own persona.

Coming to ClickUp, not only it was great to see this passionate customer base who loved our product, but it also was the challenge of how do you go and tackle this monster of so many different use cases, segments, industries. It’s this whole other can of worms. And also like a company that has more of a PLG motion, right?

So for me there was some new things that I have been excited to get under my belt that I hadn’t before. 

Margot Leong: How do you, as the first person coming into customer marketing, how do you know what to focus on? Who did you sort of turn to in that regard? How did you think about setting priorities?

Tiffany Keel: I approached that in a couple different ways. I would say like thinking about coming in, you still do have to do that legwork, right? I think the first 30 days for me, were about really talking to a lot of the sales leaders, right? And there were no big curve balls for me, which was good. I knew what I was stepping into there. There was nothing. 

And people just needed some of that baseline stuff, that foundational stuff from the start, and those things being like referenceable customers, case studies, basic advocacy stuff that you just need in a sales arsenal and in a marketing arsenal.

I really focused though on quick wins mixed with that foundational planning. At a startup, it is so important or any new company, not just a startup, that you actually showcase your value early. You really need to establish yourself as someone who is effective.

And not to say you don’t need to be like strategic and all of that. But there should be a few things that you’re hearing from your stakeholders and sales that they want, and you should be putting together a plan to execute that for sure in your first quarter. Not that you need to sign up for too much stuff, but pick the things you can do. Those quick wins.

 I would say that was my early focus. And I was really trying to think how do I actually scale this referenceable customers, how do I build pipeline for case studies when I’m starting from nothing? What would be the most effective way for me to go about that with not a lot of resources and still really trying to understand the lay of the land for the organization.

So I decided to do just a very simple outreach effort to key strategic accounts, introducing myself and introducing the concept of a reference program. I know this sounds really basic, but literally just putting that out there saying, Hey, like this is what our reference program is. Obviously, you gotta establish what that entails. 

And then just had a very simple form that’s like opt into our reference program and you get so much great information that a customer is willing to share. They opt in. I ask them, Hey are you interested in other advocacy type activities?

So I use this as not only building the referenceable library, but also this became the pipeline for me to start to get publicly facing case studies out the door. Because I think that’s really hard in the beginning coming in customer marketing at organizations, you’ve gotta talk to a lot of customers.

You’ve gotta build that pipeline. So you’re not caught flatfooted with nothing in your pipe to deliver to the sales team in a given quarter. So yeah, that was my big focus and something that was really effective at hitting a couple of my different goals.

 And from that, I probably had a hundred, 200 folks opt into the program. So it was great for me to get that list pretty quickly and it probably took me only two or three weeks to get out the door. And now sales was really starting to see at that time, okay. Wow. Okay. She’s effective, she’s starting to show the value of advocacy in the business. 

This is when I started to pitch the actual idea of rolling out a formal advocacy hub and program to truly help scale my efforts and actually bring value to customers. So I use those beginning stages to truly show the value of advocacy with those quick wins, and then use that to pitch for more resources and for bigger programs down the road.

Margot Leong: So you’re looking at those first 30 days, you got a hungry sales team. You really talk to those sales leaders to understand what they’re interested in getting from customers in order to help them sell more effectively. And it sounded like a lot of those pieces were things that you are already pretty comfortable with, right? The referenceable customers, more case study type stories. 

And then you talked about using that as a way to understand, okay, what would be some quick wins that we could do? And in terms of the quick wins pieces, was that trying to help sales move faster if they needed, okay, we need referenceable customers in these industries or these types of stories. Were those the quick wins and were you using the form and trying to generate that pipeline as a way to to get to that point? 

Tiffany Keel: Exactly. That’s exactly spot on. And great reminder. I mentioned that ClickUp had so many different use cases and industries and I think that’s the hardest part for sales, right, is having validation, customer proof, for each almost of those permutations. So yeah, doing all this was to really focus on sales enablement in the beginning and making sure that they had the right customer proof points to share with prospective customers to help them move faster in their sales cycle.

Margot Leong: So you had the form, right, which is a fantastic way to fill out some fields, and then it populates into some sort of spreadsheet or some database, then you have a place where you keep all these customers. How did you get the list of customers in the first place? 

Tiffany Keel: So it is definitely casting a wide net. For me, coming in and knowing where I wanted to focus, and probably most customer marketers wanna focus are some of your high value, bigger brand name customers. So it was drilling into those type of accounts based on also some different product usage data as well. So leveraging two different things there. 

And then getting buy-in from the CSM team to say , Hey, is it okay that we reach out to these people? Should we not reach out to these people? I wanted this to be a little more personal in my outreach versus just like a marketing email. It was like a thousand folks or something I sent this to, but I sent it from my email using just existing tools that are out there where you can send emails and batch. We use Front, you can send 200 emails at a time.

So I sent some very personal outreach to folks on this list. The buy-in was pretty easy from the CS team because we didn’t really have anything prior. There was nothing really in place. And they were very open. They saw this as more of me helping them out versus sometimes you hear where CS or other people be very protective over their customers.

I’ve been lucky at ClickUp to where it’s oh no, please. You’re just an extension of our team. Yeah, like I welcome this. Please, anything you can do to help build up advocacy is amazing. 

Margot Leong: Because basically before you came in, right, I’m assuming that if sales needed help, CSM team is usually the front lines on that.

Tiffany Keel: It was the total Wild West when I got here, it was like Slack channels, people asking, and I wouldn’t even say CS was like, they became a point person, but they weren’t accountable for it. And so it wasn’t an ideal situation for anybody, right? For the customer, for sales, for CS, it was just always a scramble and like not a great experience. 

So now that I have this list, obviously we needed a way to intake reference requests. Again, being scrappy and being new to the organization, you don’t necessarily have technology out the gate. So again, very simple form for sales to use to standardize that intake process of reference. 

Obviously there are tons of tools out there that can help with that, but that was closing the loop. It’s like, okay, we got this referenceable library now, and sales, here’s the new form that you use. Here are our SLAs. Here’s how we approach references. The Wild West is gone. We are an organized society now and this is how we’re gonna operate . 

Margot Leong: Yeah. It’s less anarchy, a little bit more trying to add a bit more structure, which at the end of the day does make everybody’s lives better. 

I was curious too, you mentioned that you sent that email, it sounded like you wanted it to look like just a sort of a plain text, regular email, which I’ve also done in the past. And I’ve found that to be very effective probably because I just think there is a certain standard when it comes to the way that marketing emails look. And I do think that if it looks very templated, people are more likely to ignore them because I think at this point you kind of think about it, it looks like an advertisement. It definitely feels more personalized. And coming directly from your email. 

Tiffany Keel: Yes.

Margot Leong: How did you pitch it? Because a lot of people, I’m sure they’ve never heard of the concept of a reference program.

How did you talk about it in a language that they could understand and get them excited to click and fill out the form. 

Tiffany Keel: Jogging my memory here. I definitely took it to the point of, hey, you were in these shoes not that long ago, right? Trying to make a decision in evaluating ClickUp. And you probably looked at things like review sites or maybe you did talk to someone who was already using ClickUp. It’s important. And wouldn’t it be great to pay it forward to others who are in those same shoes to help with their process? 

And oh, by the way, there’s benefit for you. Obviously we have a structure of swag and rewards for helping with things like that. But also, hey, it’s a great opportunity to connect with others in your space. And of course we’re gonna be cognizant of your time and we’ll only hit you up as often as you like.

 Let us know if that’s quarterly, annually, monthly, weekly. We’ll make sure that we’re not taking advantage of your time and only asking you to be a reference when appropriate. 

Margot Leong: So then talk to me about this concept of basically making sure that it’s not only about one-off request, right? How to build and frame longer term partnerships with customers. 

Tiffany Keel: Yeah, this one is tough, especially for a lot of customer marketers, right? Especially because we do help sales. A lot of times things can feel a little hectic and to try to get whatever the need is from the customer and get that ask out.

But I do think when you’re thinking about more about partnerships, it is a little bit contingent on the level of customer you’re talking to. Not always, but I think it’s something that you, certain pitches and plays are gonna be better for a more senior leader versus maybe just a day-to-day champion.

But anyways, no matter what, I think it is important to understand what’s truly motivating the customer, right? That you’re talking to. And not everyone’s gonna be perfect for a partnership type play, but you’re gonna pick up on signals from the customer, whether they are, hey, are they looking to get promoted? Are they growing their team? Are they trying to promote a specific marketing message into market? Once you understand some of those motivators and hone in on that, you start to earn the opportunity to have that longer term conversation and partnership and vision with them.

 That’s not gonna be every customer. But one example that comes to mind to me recently was this senior executive at an enterprise company that I started working with and from that first conversation I had with him, I learned out the gate, they love ClickUp.

Awesome. Okay. They had super big initiatives to get their brand, into market for the next year. And really were looking for that almost like free exposure. 

I think we talked a little bit on the pre-call, on the pre-interview, that I think we might see more and more of this, especially in this market, our customers, they’re maybe tightening budgets or they might be more open to looking at free ways, so to speak, or to tap into other people’s networks for that exposure for their brand. It’s been a big shift in my mindset with talking through some of these key customers and taking the partnership approach where, hey, it’s not just the customer doing a favor for us, right? It truly is a partnership. And we’re gonna take that approach, a lot of give, get with it and taking that sales approach as well.

Margot Leong: Yeah, exactly. If I was doing marketing for a B2B brand, especially in this precarious economy that we’re looking at, what are the available options? One thing that might be interesting is to take a look at all the vendors that you’re working with already. Look down that list, see if any of them would be interesting to partner with more on the exposure side. 

So for example, ClickUp, I think they’re a pretty big name in the space in a very short amount of time. You know, you think about it, hey, like that would be some interesting exposure. Why don’t I go to them directly and say, Hey, we use your product. The team that uses it seems to love it. They’re on board to do a testimonial video, like whatever you guys want. There’s something really interesting about that.

Tiffany Keel: Hmm. I’m getting some really great ideas, Margot. Maybe I could do some like outreach that’s more tailored to that messaging and see what comes back, right? 

Margot Leong: A hundred percent. Why not leverage that and leverage the power, right? You are looking for customers to feature and they are wanting to get featured. That’s massive for them in so many different ways. That’s free marketing all around. And it’s a different way to look at partnerships and that I think most companies are just not really thinking about leveraging. I think it’s pretty interesting as a pitch.

Tiffany Keel: All right. I like it, that’s my 2023 play, Margot. I love it. 

So I’ll go back to talking a little bit about this one account. I think we all feel this pain of it’s pretty hard to get engaged with senior level, C-suite folks at enterprise accounts, right? So once I got my foot in the door, we really started to put together these different milestones over a five month period. And for us, with me working with this customer, it was like, let’s get a case study going first. Let’s get that going, get that written, approved, solidify some metrics.

And then we decided, hey, once we got that approved, we would use that to continue the relationship. Let’s prove we can do that together. And then we would use that to facilitate an actual video testimonial. And I said, we would invest budget and money to do the video testimonial with them. So that was that next step in the journey. 

So it’s great. We have this little kit: video testimonial with the case study. And then, oh, by the way, our marketing calendar, we have our big user conference coming up, right? So we use that to then use that content, get them to speak at the event, was the next continuation, right?

 And then we have an awards program like we do at many virtual events and in-person events. And so we throw their name in the hat for that as well, and then talk about potential PR we can do coming out of that. 

Prove together we can do one thing almost and earn the right to do more things and really prove to each other you can be good partners for each other. Really think about anchoring your customers’ initiatives and goals into your existing programming and in your own goals. And I do recommend coming to your calls prepared with either like a deck or a proposal or an overview of opportunities. You want to take a true partnership sales approach to it to show you mean business. That’s been my approach to thinking more partnership versus ad hoc. 

But I do think it is contingent on making sure you are talking to, sales speak, a very qualified advocate. 

 I think the more personalized you can get right, I think is key. And you know, as much as we want the partnership to go on forever, there will be a pause and you’ll hit them up for something, right, three months down the road. You want them to be ready and willing to help. So, yeah, I think the more you can invest in these relationships, the better for those key accounts. 

Margot Leong: And tell me about how your focus on the advocacy side has evolved now that you’ve been at ClickUp for a year, which I’m sure has probably gone by super fast. But a year can go by so quickly. So yeah, give me a sense of how things have evolved and how you’re thinking about things coming into 2023. 

Tiffany Keel: Totally. I’ve just gotta say it feels like five weeks and five years at the same time. Most folks know startup life. For 2023, I think my big focus and how things are shifting is just getting more and more strategic about the customers I’m engaging. The foundation has been set, right? Like when I started, there were no case studies. Now we have 28 or something like that, hit on a lot of key use cases and personas. 

But now it’s really double clicking into some of those really key use cases and helping bring more customer specific content to market for our demand gen teams, our sales teams. I think it’s just getting more and more strategic and focused on the more important use cases for us. 

I’m a team of one today. And scaling out advocacy and creating more engines for low effort advocacy asks is going to be a big focus. Things like reviews or just even people opting into our reference program or posting things on social, I call those like low effort advocacy asks. So important for me to have an engine to do that because I don’t have that much time. So I want always on engines that are churning out those things so I can focus on those high effort, high value advocacy activities, talking about those partnerships with key strategic customers.

Margot Leong: You mentioned having more formalized community for ClickUp, is that part of that strategy essentially to utilize that to help scale some of these pieces? 

Tiffany Keel: A hundred percent. A couple months ago, we finally soft launched our advocacy community program. It’s called Verified VIP. And this has really become the engine for these asks. But the whole idea is you gotta keep that engine fueled, from getting people into the program, engaging people in the program.

The focus is gonna be on how do we even scale what we already have in place and just continue to take advantage of those really happy vocal customers who are a part of the program. 

Margot Leong: Coming from as someone who’s done something similar, right, when you’re in the first sort of throes of gotta get this done, gotta get the foundation, gotta show that we can do this. You are thinking about it all the time, right? 

And then when you get a chance to step back, you also start to develop an understanding around what the charter or the mission for what you wanna focus on in the future and how you wanna define customer advocacy as well. All of that evolves, especially as you get more confident in what you’ve been able to build so far, and you get more understanding of the organization and how it works and what they’ll respond to. 

So now that you have some of those building blocks in place, how you are defining and explaining what customer advocacy does now?.

Tiffany Keel: Totally. And it’s funny, you would think it would’ve evolved a ton, but honestly I feel like for the organization, I gotta keep it simple. Just so they understand what customer advocacy and what customer marketing is. 

I always say, it is my job to ultimately activate all of these super fans that we have, all these like raving fans to share their ClickUp successes with the world. And then it is my job to take that, bottle it up and infuse it back into our sales talk tracks, our demand gen campaigns, our overall brand narrative. At the end of the day we do this so we can help the business continue to grow. And it’s like a key glue to a lot of the existing programs and departments that we have. 

That’s usually how I describe it just to make it very plain and clear for folks who aren’t as familiar with customer advocacy. Maybe a resolution for me for 2023 here is to rethink if I wanna tweak that.

Margot Leong: In your previous experience at ON24, you were also pretty involved on the overall customer journey side of things too. So you’ve got experience on what we would think about as lifecycle marketing, customer marketing. I know that at ClickUp, you’re really focused on advocacy. I’m curious if you think about that at all, right, or think about how you want to inject that in the future. 

Tiffany Keel: Gosh, I’ll say at ClickUp, our marketing team has ballooned and we have experts who do a lot of that life cycle marketing, which is awesome. My true passion is advocacy for sure. It’s just a lot of fun for me, because you get more on that personal level . 

But that being said, advocacy has a journey as well, right? I can now, after a year here, think more about all these different touchpoints we have, right? Like infusing advocacy into that life cycle. Some of those things we think about, you know, post renewal. How do we wanna approach advocacy at scale in an always on way, taking advantage of the different channels we have, whether that’s email or in-app or like activating our CSMs through something, right?

There’s a lot that can be done there versus right now I would say it feels like a lot of effort on my end, right? But how do we continue to create that always on engine of advocacy, even outside of a program like our Verified VIP Influitive program, right? How do we tap into other marketing tactics to drive advocacy everywhere our customers are? 

Margot Leong: One of the last questions is, we have a lot of people that are just getting started in customer marketing, maybe a few years into their career. If you were to speak to your younger Tiffany self, what advice would you give yourself? 

Tiffany Keel: Take vacations. It’s ok. First thing. It’s ok. You can do that. 

But I would say a big one is take advantage of this growing customer marketing community that’s out there. Talk to others in the space. Learn from their mistakes, their successes. Customer marketing is not a new discipline, right? People have been doing it for a long time and you don’t need to recreate the wheel.

There are definitely some plays you can steal and tweak and bring some great impact to your company. So I would say that is one piece of advice. 

Margot Leong: I definitely resonate with that. Like I feel as though when I was just starting out, a lot of this was based off of intuition and hunch definitely not as many resources that existed.

But I also didn’t make as much of an effort to reach out to people in the space and to learn from them. It was a lot of it of being on this island and figuring it out. You know, now that I’m a bit older, looking back in my career right, the opportunity that you have to be at a company doing, work that you hopefully really enjoy, you’re getting paid to learn, right?

I would absolutely take advantage of that opportunity. If your company has things like L&D type development, honestly, I never took advantage of those things and I really wish that I did. I was afraid to ask for budget for my own learning. I really would push for that if you have the opportunity. 

And honestly, I think not being afraid to take a little bit more risks in terms of how you are reaching out to customers or the types of customers you wanna reach out to. Or even just building more relationships within the organization because really that’s what greases the wheel to get your work done.

 To your point about take advantage of the community, it really is some of the kindest, nicest people, which makes sense because if you like to talk to people, you think the best of other people, right? It really feeds into itself. 

Tiffany Keel: I’ll also add that I do think advocacy is an evolution. Don’t beat yourself up, you know? Being new to a company, feeling like you need to boil the ocean and do everything at once. First starting out there feels like there’s so much you could be doing, right? I have to start a CAB, I have to do our user conference. I have to do da da da da, right? 

Focus on the foundation, the mechanics of advocacy when you’re first starting out. Think about those core competencies that you can really own, that you can take from business to business. Once that foundation is established, you can start to do bigger and more creative things. Obviously take those risks, right? 

 I feel like at ON24, I was there for four or five years and it really wasn’t till past year one, I could really get outside the box, truly earn the right to be like, yeah, I think we should do this. It might be a little risky, but here’s why it’s worth it. 

Margot Leong: Yeah, absolutely. The mechanics, right? The fundamentals of what you’re doing. You have to understand how to work those levers. You kind of have to pound the pavement as it were. This whole customer database, how do I then move forward and start building those relationships with customers to then start working and understanding how to utilize them, right?

And even that in of itself takes a while because you’re talking about real human relationships here, right? You’re talking about real people and of course all the internal stakeholder management that goes along with it. Seeing outside of that, to your point, doesn’t often happen until you’ve actually done the work and understand what all of that entails.

But yeah, once you can start to see outside of that, being open to thinking a little bit outside of the box and taking some of the best ideas you hear from the customer marketing community and implementing those faster, I think is all really good. 

Tiffany, this was such an incredible conversation. Really excited to see what you’ll be focusing on in the coming year. But if people are interested in getting in touch with you, where’s the best place that they can connect with you, whether it be like LinkedIn, et cetera. 

Tiffany Keel: You can find me on LinkedIn. I’m pretty responsive and I’ll even throw my email out there. It’s just Hit me up. Happy to have a conversation with anybody and everybody about advocacy and customer marketing. And Margot, thank you for having me. This has been such a fun conversation today. 

Thanks for tuning into this episode of Beating The Drum. For more interviews with advocacy leaders and tips on creating customers that will sing your praises, head on over to our website, If you enjoyed today’s show, please subscribe on Apple Podcasts, Spotify, or wherever you get your podcasts and don’t forget to rate and review us. If you know someone that would be a great fit for the show, I would love to hear about it. You can reach out at Take care, everybody. 



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