Welcome to Episode 202! Karen Peacock is the COO @ Intercom, the company that provides a new and better way to acquire, engage and retain customers. To date, Intercom have raised over $240m in VC funding from some of the very best in VC including GV, Kleiner Perkins, Bessemer, ICONIQ and then individuals such as Mark Zuckerberg, John Collison, Biz Stone and Andy McLoughlin. As for Karen, prior to Intercom, she spent an incredible 17 years at Intuit leading all of Intuit’s small business products and services worldwide, a $2.2B business including QuickBooks, Accounting, Payments, and Payroll. As part of that, Karen managed a team of 500 and helped build one of the world’s largest SaaS businesses.

In Today’s Episode We Discuss:

* How Karen made her way into the world of SaaS with Intuit and how that led to becoming COO @ Intercom today. What were Karen’s biggest takeaways from her time at Intuit?

* What does Karen mean when she says, “Watch what customers do, not what they say?” How does Karen think about the difference between being customer driven vs customer informed? Why is it important to fall in love with the problem and not the solution as an entrepreneur?

* Karen has grown Intercom from 350 to 600 in 18 months, what would Karen’s biggest advice and learnings be when it comes to team assembly and hiring the best? What can one do to stress test the fit of the candidate pre-hire? What does Karen always find to be the most revealing questions to ask?

* When does Karen believe is the right time to hire a COO? How does one know when they have the right COO fit? What are some best practices for onboarding a new COO? What is the optimal relationship between CEO and COO?

* Karen has seen incredible scaling first hand both with Intercom and Intuit. What would some of her biggest takeaways and advice be on scaling? Where does Karen see many make mistakes in the scaling phases? What does Karen mean when she speaks about “the most important metric that you probably aren’t tracking?”

Karen’s 60 Second SaaStr:

* What does Karen know now that she wishes she had known at the beginning?

* What motto or quote does Karen frequently revert back to?

* What is the most challenging element in Karen’s role today?

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Jason Lemkin
Harry Stebbings
Karen Peacock


Harry Stebbings: We are back for another week in the world of SaaS with the official SaaStr podcast and me, Harry Stebbings, @hstebbings1996 with two b’s on Instagram.

We have a very special episode today. For long time listeners you’ll remember our having both Des Traynor and Eoghan McCabe, founders of Intercom, on the show before. I’m delighted to welcome their incredible COO to the show today, Karen Peacock.

For those that don’t know, Intercom is the company that provides a new and better way to acquire, engage, and retain customers. Using Intercom is a proven way to improve your website and in-app conversion and engagement and drive business growth. To date, Intercom has over 30,000 customers and has raised over 240 million dollars in VC funding from the likes of Kleiner Perkins, Google Ventures, Bessemer, Index and ICONIQ and was most recently valued at 1.275 billion dollars.

As for Karen, prior to Intercom she spent an incredible fifteen years at Intuit, leading all of Intuit’s small business products and services worldwide. A 2.2 billion dollar business including QuickBooks, Accounting, Payments, and Payroll and as part of that, Karen managed a team of 500 and helped build one of the largest SaaS businesses in the world.

I do want to say a huge thank you to the wonderful Mallun Yen for the intro to Karen today. I really do so appreciate that.

That’s enough from me, so without further ado I’m very delighted to hand over to Karen Peacock, COO at Intercom.

Karen, it’s such a pleasure to have you on the show today. Huge hand to the one from Mallun Yen and Des Traynor for the intro but thank you so much for joining me today.

Karen Peacock: Great to be here, Harry.

Harry Stebbings: I would love to kick off today with a little bit about you. So tell me, Karen, how did you make your way into what I know to be the wonderful world of SaaS and come to be COO at Intercom today?

Karen Peacock: Absolutely. Before joining Intercom I was the SVP of Small Business at Intuit and I was responsible for all of Intuit’s products and service for small business like QuickBooks, Accounting, Payroll, Payments, that’s about a 2.5 billion dollar business. Both at Intuit and at other places I have led different SaaS businesses.

I started a SaaS business within Intuit and grew that from zero to about 40 million in revenue. Took another business from 30 million to about 100 million, led another business from about 100 million in ARR to about 500 million in ARR. All in the SaaS world. I’ve had the opportunity to work with lots of different types of SaaS businesses and at lots of stages which has been super fun and great learning for me.

Before running businesses my background was really in a combination of both product and marketing, as well as data, and the technical background, I like to occasionally code on the side. I have a particular interest in machine learning and data and I joined Intercom about 18 months ago because the first time I saw the Intercom product, which was about two years ago, was truly a lightning bolt moment for me. I looked at the product and I thought, “Oh my God, this is the product that I have needed in every SaaS business I’ve ever run.” I felt that customer need first hand and I thought, “Okay, this is something big,” and I not only saw it where it was then, but I had a vision for where it could go and I just got super excited about it.

I got to know the team and that was the next big reason why I joined Intercom. It’s a really special group of folks. You mentioned Eoghan McCabe and Des Traynor, both prior guests for you, Harry, I know, and those folks and the rest of the leadership team are people who are incredibly smart yet, very much down to earth and humble who are really high vision and yet open minded and not all those adjectives go to people all the time. A really special group driving amazing growth from a business perspective and a place where I thought I could make a big difference.

Harry Stebbings: Eoghan and Des are fantastic, but how could I not take the opportunity while I have it? You mentioned the multiple lines of business that you grew, at different stages but all incredibly significantly, how could I not ask, what were some of the big takeaways maybe from your time at Intuit, how do you think that impacted, maybe your operating mentality today?

Karen Peacock: Yeah, I took many things away from my time at Intuit and maybe I’ll share two that really rise to the top. One is Intuit has always been very much focused on customers so I just got ingrained in me early on to spend time with customers, to watch what they do, to talk to customers, we had a concept we called the “follow me homes” which is the idea of following a customer to their home or to wherever it is that they’re interacting with your product or service. So, spending deep time with customers, building customer empathy and really understanding their problems and needs and that’s something that I’ve very much done at Intercom as part of the Intercom DNA as well. Really spend time with customers for any stage of business, I think, is a great learning and piece of advice.

A second big thing that I learned at Intuit is the idea of having a big vision and taking it one bite at a time. A big vision where you take it all at once ends up in a situation where you’ve got a great big idea, an idea that you think is great, it’s probably big and then you spend years working on it and you do an unveil and you realize it was off in some important ways and it’s very important to have that big vision but take it that one bite at a time. Kind of a lean start up methodology.

That’s very much also very similar to the way Intercom thinks and, in fact, Intercom has a value which is, “Think big, start small.” We have a concept at Intercom called the cupcake, the idea is a cupcake is the smallest possible test of the core idea. The point is, you’re testing the core idea, the big leap of faith. You’re not testing things around the edges like the icing, you’re testing the core idea there so in both cases and for me very much learned at Intuit, was the concept of starting with the big vision, big idea. If you just start small without a clear big vision, you’ll also end small.

Harry Stebbings: Can I ask, you mentioned the bite by bite there. How does one determine those milestones? Is it most often in revenue milestones, is it in product upgrade and improvement milestones, is it in team scaling milestones? How does one measure the bite by bite, so to speak?

Karen Peacock: Yeah, so I’m all about learning so I think you measure that bite by bite around learning. What is it that you need to learn? Probably the first thing that you need to learn is, are you actually going after a real customer problem? A second might be are you actually successfully solving that problem? You might measure that by, are people actively using your product on an ongoing basis even after you walk out their door? Are they actively reaching out to you asking for more and more, which means they’re engaged and they care. Are they willing to actually pay for it? In which case, that’s showing kind of the next level of care. So, I think about it as key learning milestones and what you can learn from your customers in terms of there engagement and willingness to pay and therefore the value that you’re creating for your customers.

Harry Stebbings: I love that element of the learning milestones. I do, though, want to kick off though today–it’s going to be a blockbuster of an episode for sure, because we’re going to break down some of the biggest challenges that most SaaS founders come to me and I’m sure you with. Starting on finding product market fit, then moving to hiring and building that team, and then all the challenges that come with it. Does that work for you?

Karen Peacock: That sounds great.

Harry Stebbings: Okay, so starting on the mythical product market fit, we had Elad Gil on the show recently and he said the sole job of the CEO in the early days is to keep the company financed and to find product market fit. Imagine I’m an early stage angel investment of yours Karen, what advice would you have for me on finding product market fit?

Karen Peacock: You know, it’s funny that you say that because it’s actually very similar advice that I give to companies of all stages around product market fit, and for me, it’s hard-won advice from a big failure of mine, and so I’ll share it and then net it out for you in a couple of key pieces of advice that I think particularly apply to early stage but also apply to across the board.

When I first became the director of product management for QuickBooks, I wanted to do something big and I really wanted to launch something that we had never done before, make the product dramatically better, launch a new–whether it was product or feature or something that we had never done before, not just incrementally improve. I went out and spent time with my team, with customers and we asked them, “What are your biggest unsolved problems? What do you most wish for? What is it that QuickBooks could do or be that would be so much better than what it is today?” The number one thing that we heard back from customers was budgeting. Small business owners said, “We want budgeting,” so we said, “Fantastic!” We can build a great budgeting solution and we set off to do that.

We prototyped and we had customers, we showed those to customers and we got customer feedback and we got to the point where people said, “Yep, this is a good budgeting solution,” and we built it and we shipped it and, Harry, you know what happened? Why did nobody use it? People said that was exactly what they wanted and so we went out and spent time back with customers and this time we didn’t ask them what they wanted, we instead watched them and we watched what they did and what we found was there was not a single small business owner who actually sat down to do budgeting and struggled through it. What they instead did was they got a stack of bills, either online or physically, and they went through them. They shuffled through them, they figured out, “Here are the ones that I can pay now, here are the ones that I can’t pay now, here are the ones that I think I can push off,” and so their real problem was not budgeting. They never actually did budgeting.

The first piece of advice that I would say is, watch what customers do, not what they say, because here nobody actually did budgeting. What they did was go through their bills to figure out what they could actually pay and so we realized that the real problem wasn’t budgeting, the real problem was “I can’t pay my bills, help me with cash management so I can pay the bills that matter to me.”

That led to my second aha, my second big piece of advice which is to fall in love with the problem, not your solution, and it’s very easy to fall in love with the solution of, “We had this great idea as a start up that we’re going to create this business around whatever it is, we’re going to create the next best budgeting solution,” and you go out and you talk to people and they say, “Yes, I need budgeting,” you talk to your friends and they say, “That’s a fantastic idea!” But you haven’t actually fallen in love with the customer’s problem. Make sure you fall in love with the customer’s problem.

What we did in this case is went back to scratch and step one and thought about the real problem of having enough cash on hand. We ended up building out a solution for that, which is really around cash management. What happened was, we got immediate usage for that and there are now hundreds of thousands of small businesses around the world today that use that product.

Harry Stebbings: I mean, I love those takeaways and learnings. I am super intrigued, you mentioned there about watching what people do not what they say. I’m always very torn between the element of customer-driven versus customer-informed and there’s a huge amount of customer love and customer centricity that we hear about today, but how do you think about that and not doing the Henry Ford of, “If I did what customers asked I’d build a faster horse.” Do you think it’s quite that easy?

Karen Peacock: You know, I think it takes a little bit of iteration between the two, really making sure that you understand why they’re doing what they’re doing, why they’re not doing things that you would think they would be doing. In this case, there’s the aspirational problem of, “I think I should be doing budgeting, but it’s something that I actually never do.” When you watch what people do, that gives you the greatest clue and then you can ask them why they’re doing certain things or why they’re not doing other things and then you can also show them new ideas and rather than having it be a big reveal after a year or two of work, you can show them the ideas along the way and I do think customers will do a pretty good job of giving you good feedback on your idea, so it can be very much a combination of the two.

Watch what they do, not what they say, but do ask them why and then when you build rapid prototypes, it can be just sketches, it can be bubblegum and paperclip versions, and then I think you can get good feedback from customers along the way that way too.

Harry Stebbings: I have to ask, Karen, we mentioned obviously the different levels of product market fit there, you’ve grown and scaled organizations at different levels. It’s normally only attributed to the very early days product market fit, so I’m interested, is it applicable to multiple stages, or do you think it really is solely that zero to a thousand customers so to speak?

Karen Peacock: I think product market fit matters at every stage of a company’s life cycle. Companies that feel like you’ll get to a point where you’ve achieved this nirvana product market fit and you can check the box and move on and focus on other things, are the ones who get disrupted in the future. As they say, the pace of change has never been as fast as it is today and it will never be as slow again. What I think you’ll find is if you think by getting product market fit you can check the box and move on, you will get disrupted and instead you must focus on getting better and better product market fit, both in your core product as well as in adjacent areas. I actually think it’s an ongoing skill and ongoing thing that the CEO and the key folks in the executive team should very much obsess about on an ongoing basis.

Harry Stebbings: You mentioned the executive team there, I do want to move to the second element of the core problems that founders come to me with, which is the secret sauce behind hiring. You’ve worked with many stellar teams. I’m really interested, over the last 18 months at Intercom you’ve gone from 350 to 600. I have to ask again, pretend I’m one of your early stage angel investments. What advice would you have for me in assembling this incredible team, having done it so well with Intercom?

Karen Peacock: I believe that you can apply lean start up principals to most things in life. You should have got that.

One of the things that I believe you can apply those principals to, is hiring. Figure out how you can do a lean test and the way that I do that is I try to put people in the job. Rather than asking a lot of hypothetical, somewhat interesting questions, but very theoretical, give people the kind of work and the kind of questions that you would actually give them if they were in the job, see how it goes.

Whether that’s a real time conversation that you’re working on a real time challenge or opportunity or whether that’s a take home thing for them to work on and give a few hours of noodling over to a particular challenge that you’re facing right now or particular area that you want this person to lead or think about. When you put people in the role, you get a much much faster and more accurate read.

The second thing that I do that I’m a big believer in is what I call back channel reference checks. Figure out who you know in common with this person, it could be someone you know directly or a friend of a friend, who has worked with this person before and get that reference. Yes, everyone always gives you references when you’re maybe in the final stages of hiring but you know what all those references are going to say because they’re hand picked to be incredibly positive, so find people who you know in common with the person and get those references.

I do think it’s super important to do that with the utmost of confidentially and only do that at the very, very final stage, so just with the final one or two candidates and I never get reference checks from a company that the person is currently still working at so you want to very much protect their confidentiality just like you’d want the same for you.

Harry Stebbings: I totally get that and I love that back channeling, sorry, go on.

Karen Peacock: I was going to say, I think the same also applies when you’re thinking about taking a new job. If you’re thinking of joining an early stage company, go work there for a few days or for a week or for a few weeks. It will be the best investment of your time that you could possibly make. You will learn so much about the team and the company, they will learn so much about you and then you can make the decision. I think often times, especially for more senior folks, if you hire someone or offer yourself as an advisor first for whatever period of time, you’ll learn a lot that way.

Harry Stebbings: I love that freemium style.

Karen Peacock: Yes, exactly. The free trial.

Harry Stebbings: Yep, it’s the best approach. I do have to ask you, you mentioned there about giving them work that’s maybe applicable to what they’d actually do. In terms of character and culture assessment, I’m a big nerd for interview questions. Do you have one or two interview questions that you always love to ask that you feel really, reveal and show the character and culture fit potential of a person that’s sitting in front of you?

Karen Peacock: I always like to think about trajectory and whether that’s a person’s trajectory or a business trajectory, so I like to figure out if the person is a learner. Are they open minded? Are they humble? Are they down to earth? Are they getting better every day? I’ll try and assess that in the interviews that I do and I’ll ask questions around “what did you learn from that?” or “tell me something that you learned from that and how you applied that?” And I look for specific examples of both what they learned and then what they did differently in the future. That will show me if they are a learner or not, that they have humility to realize that they aren’t always right on everything, and that they either can or can’t take fast action and really put that learning in place and start to use it. Really just asking round what they learned and to share examples of how they applied that in the future.

Harry Stebbings: I feel I should be taking notes here, Karen, I do have to ask, in the role of COO, is so in vogue, in fashion right now and from our private discussions I know you’ve differentiated opinions on COO and hiring. So, what advice would you have for me on a couple of different points. Let’s start with fundamentally, when is the right time to hire a COO?

Karen Peacock: There’s no one single perfect answer to that. Some of the principals that I’d have in mind are first of all, you always need to hire fantastic, functional leaders for the key functions of your business. Say if you’re in a software business that’s probably having an amazing head of product, head of engineering, head of marketing, head of sales, depending on your sales motion and some key functions like that. Hiring a COO does not replace that need.

If you get to the place where you’ve got a sufficient level of complexity that you want a senior level leader and partner to work across multiple different disciplines and functions and bring those together, that can be a great time to think about a COO.

I also think that as a CEO, you should not hire a COO unless you’re willing to let someone else drive the bus from time to time so you have to be willing to give up some level of control to just get a line on principals and goals and just to know the person’s going to do some things exactly as you would do them and some things differently. Some of these things you’ll love and some of them you’ll think, “Hmm, maybe I could have done it a little bit better.” If you hire a COO and don’t give them room to run, that’s not going to be good for you, the COO, or for your company so only hire a COO when you’re ready to give them autonomy and give them real space as long as you’re aligned on principals and values and goals.

Harry Stebbings: Can I ask, how does one know when they’ve found the right COO fit ,and is it one where you can do the freemium model again so to speak?

Karen Peacock: I am a believer of that freemium model, as you know, and one of the things that Eoghan McCabe, the CEO of Intercom, and I did was we actually were talking for about five months before I ended up joining Intercom and that was a great way for the two of us to get to know each other, understand and basically talk through a number of business situations that Intercom was facing or that I had gone through and talk about what we’d do in different cases, pros and cons, so I think getting to know the person over an extended period of time is incredibly valuable.

I think enlisting the person as an advisor to the business for a period of time is also a great way to use that freemium model and I do think that the single biggest piece of advice that people give CEOs about hiring a COO is fundamentally flawed. Or maybe half the story. That is a lot of the advice CEOs get is think about all the things that you love to do and write those down. Now think about all the things that you don’t really like to do and that you’re not very good at and yet do matter for your business and write those things down. Now come up with somebody who loves and is great at all the things that you don’t like and are not good at. I think that’s only half the story because if you literally do that, you’ve now just hired somebody who is your polar opposite.

What I think you’d want to do instead, is hire someone where you have complementary skills and are good at some of the things that you have less experience or less desire to be good at, and also, though, have some common values, common principals, common things you care about so that there is some overlap that you can go back to when there are tricky times. You can come back to your shared principals and go from there.

Harry Stebbings: Yeah, no, I love that kind of thinking. I’m sure our principals for when those trickier times and you need alignment so if you can take that a little bit further, your freemium journey and advisorship with Intercom and now you’ve joined Intercom, tell me, what’s the best practice for onboarding a new COO? Is there a right process or framework?

Karen Peacock: One of the things that we did out here I think worked pretty well and it’s a little bit unusual and I’ve now done it with each of my direct reports that I’ve hired, and that is, when I first joined Intercom, for the first six weeks I had no direct reports and no specific operating role or jobs to be done. It was just focusing on onboarding.

I took that first six weeks and I went out and as you mentioned, there were about 350 people when I joined Intercom, I probably talked to, either one on one or in small group settings, with about 150 people to really understand people’s perceptions of what was working well, what wasn’t, what were some of our biggest opportunities ahead, what they most wished for, to really kind of get embedded in the company and the ideas. I spent a lot of time with the leadership team and I spent a lot of time with customers, as you might expect from earlier in the conversation.

I met with probably about 30 different customers and watched them use Intercom and whether that was several customers I got to watch setting up and using Intercom for their very first time, a number of customers I got to watch using Intercom for their 1001st time. Watching customers use our products, seeing how they used it and in the fullness of everything else they were doing for their business was super powerful. I also took a rotation in customer support, actually using our products to support our customers using our products and using our product to sell our product and so both learning about Intercom and our products and our customers along the way.

Harry Stebbings: You mentioned the customers there and serving them with the Intercom product itself, I love that double, that’s brilliant. You now have thousands and thousands of customers around the world and we’ve moved into the scaling phase so to speak. We’ve assembled the perfect team and we’re ready for the final element and it’s a question I often get as well, which is how do I get scaling right? As we said, you’ve seen it before with incredible scaling within Intercom, within Divisions and then also within Intuit. Having seen this first hand, what would be your biggest lessons and advice here, Karen?

Karen Peacock: Yeah, I think it’s very easy when you just have a handful of people to be aligned and know what each other is thinking and be headed in the same direction. When you start getting to 50 or even a 100 people, you really need to make sure that the whole company understands where you’re going, why, and how their work contributes to it. You also need to make sure that you make the space for the teams and people to be autonomous and get the best ideas on the table and figure out how to bring those to life.

I think it’s important just to be very clear on the problems that you’re solving. At Intercom we’ve designed this system which we call “how we work.” What we do is we start with our vision, which is to make internet business personal. We’ve always been very clear on that mission. We’ve also built out a customer promise and this is something that we just did really over the past year. That is, we promise our customers faster growth through better relationships and that’s been very aligning for us to get clear on what is our brand promise and make sure that in our products we’re actually focused on building those out in everything we do and that our marketing is clear on that, our sales is aligned against that.

We start with that vision, mission, and brand promise.

We’ve then built out a company strategy and that’s just a short three page document. We keep it regularly updated, we share it with every new person who joins. We share it with every new manager as they get promoted, we share it with every director as they get promoted, and then we also share and re share with the company twice a year.

It feels like potentially a lot of repetition but as you get bigger, you’re going to need to do more of that and realize that for many people it’s only their first or second time they’ve heard it, even if you as a CEO have said it 10 or 50 times. It’s well worth repeating and super important too, so really being clear on your strategy, having that written down.

What we then do at Intercom is we have a series of what we call “programs,” and these are multi quarter initiatives and key elements that bring our strategy to life. For example, we have one around automation, so helping our customers build these better relationships and grow their business at scale. We have one around our app eco system in moving to become a platform and then each of those programs, we’ve got about 10 programs, has a leader and a cross functional team and within that, they develop a set of goals, those goals for the quarter and ongoing goals beyond that.

We then pull up as an exec team and work together on those to make sure we’re all aligned to get the best ideas out there and then bubble up the top few to be company level goals so really being clear on that mission and vision, the brand promise, being clear then on the multi quarter programs of work that you have and then they key goals that you have for the quarter so that each person knows how their work ties in to the overall goals and mission and vision for the company and so that each person can be creative in getting the best ideas out there and creative in how they bring that to life.

Harry Stebbings: Can I ask, Karen, so many intricacies and moving parts there within the organization, where do you see many going wrong, maybe, in this scaling phase of the company building story?

Karen Peacock: Yeah, I think a couple places. One is a lot of times people lose focus on the customer. They lose focus on the concept of product market fit and that’s easy to kind of focus so much on your own systems and processes and your own things that are going well or aren’t that you lost focus on your customers. Always keep coming back to your customer, that’s your true North.

I also think that sometimes businesses put in either too much or too little process. Too little process, what that looks like if you’re in that situation is people aren’t clear on the strategy, they’re pulling the team in different directions. There’s lot of questions that they need to come directly to the CEO to get answered versus just being clear on where you’re going. That’s what too little process looks like or too little structure.

Too much structure or process looks like your teams are spending a lot of time filling out documents, sitting in meetings reviewing the same things over and over, and not enough time actually being inventive and creative and actually building.

Harry Stebbings: Speaking of strengths there, you mentioned the orgl chart design and how you let each person know the value of their input, it very much seems like a strength of yours, but when we chatted before, and this is one that I do normally save for the 60 Second SaaS Quick Fire Round, but you said to me before the show, there’s one strength that’s the most underrated. So what is that strength, Karen and how have you maybe used it in the real world?

Karen Peacock: Yeah, so, I think the most underrated strength around is hindsight. We all talk about hindsight is 20/20 and then that’s the end of the sentence. Yeah, hindsight is 20/20, so use it.

One of the things that I do typically at the end of each quarter and certainly at the end of each year is I think about where I spent my time and I did thousands of different things and what were the three things that really most moved the needle for the company and then how can I spend more time on things like that in the future?

For me, this past year it was things around focusing on automation, helping our customers drive growth at scale. Another was around moving from being a product to being a platform, and a third area was around focusing on customer value. One of the things we’ve gotten much, much more clear on is the value that we deliver to our customers.

For example, over the past year we actually measured for our 30,000 customers when they use Intercom, we found that on average our customers increase their conversion rates by 82 percent when they start using Intercom so we’re delivering on that promise of helping our customers drive growth. Customer value is another key area that I really look back in hindsight and say, “Yes, every minute that I spent on that was time well spent.”

So, I’d encourage you, Harry, and anyone else listening to our podcast as well, just reflecting on your last month or your last year, think about all the things you spent your time on and now think about the three things that really most moved the needle for your company.

Harry Stebbings: I’m doing that now and I need your advice here, Karen. I’m doing that now and it was the coffee with a friend where I got recommended a deal, another was a serendipitous meeting with someone that I didn’t particularly want to have a meeting with, and it all seems rather serendipitous. Is that the role of the VC that I should negate myself from this or is there actual beauty in the hindsight here that I’m missing?

Karen Peacock: Well, I do think that there’s always a space for serendipity. Maybe it’s about making sure that you carve off enough time in your typical week for the unexpected conversation and the value that you get from that and you might say, “Great, I want to dedicate, whatever it is, 10 hours a week,” in your case, probably less for someone who’s operating a core business, to just serendipitous conversations and then let me evaluate at the end of the month whether I feel like that was time well spent or whether there–of the ones that were most valuable, how could I have known that in advance? How could I have narrowed down that time to the ones that were most efficient and effective.

My guess is there were some leading indicators there if you just think about those conversations that were most exciting that might have given you a hint that, “Huh, this could be a particularly interesting one,” and then just making sure that you give yourself the time to do it.

Harry Stebbings: My word, Karen, I wish you were here with me. I’d be so much more efficient. I do want to move into a quick fire round here now. I say a short statement and you give me your immediate thoughts. About 60 seconds or less, how does that sound?

Karen Peacock: That sounds great, thanks.

Harry Stebbings: What motto or quote do you most frequently revert back to?

Karen Peacock: My favorite motto is, “Good decisions come from good options.” My follow up there is so your job is to create good options and if you have a situation where you don’t like your options, your job is to come up with more, then make decisions, so, good decisions come from good options.

Harry Stebbings: I love that. Do you agree with a good decision made today is better than a perfect decision made tomorrow?

Karen Peacock: I do. Although I would say a bad decision made today is worse than a good decision tomorrow, as well.

Harry Stebbings: That’s very important distinction. Tell me, what’s the most challenging element of your role with Intercom today?

Karen Peacock: I think the biggest thing there is there’s so many places where I could spend my time. Priorities that I know if I spent time on, I could really help improve things for the company, for customers, for the business and so the most challenging thing is really round prioritization and focus and choosing where I spend my time and where I help the teams choose to spend their time.

Harry Stebbings: What do you feel are your personal strengths and weaknesses, Karen? Self reflective here.

Karen Peacock: Plenty of weaknesses and a few strengths in there. I think one of my key strengths is that I like to and am good at thinking at all different altitudes. Whether the 50,000 foot level or down at the 50 foot level and so a strength of mine is I’m comfortable and enjoy engaging at all different levels and I typically know when to go high level and when to deep dive and how to come back up.

Harry Stebbings: Then the weaknesses?

Karen Peacock: Sometimes I make assumptions when I should pause and ask more questions and whether that’s assuming that all the right people cross functionally were involved in a decision or assuming that someone else had done a deep dive in an area that I would have if I was focused there or assuming that we’ve got certain tools or processes or infrastructure or systems in place where we don’t yet. So, sometimes I make assumptions there when I should be asking more questions and then I usually figure that out and realize, “Okay, actually it’s my job to help build those things out.”

Harry Stebbings: I think we both share the weakness of assumptions there. I’m very much with you on that but I want to finish then, and this is one of my favorites actually, what do you know now, Karen, that you wish you’d know at the beginning? This can be the beginning of your time with Intercom, with Intuit, or the beginning of dot dot dot, but what do you know now that you wish you’d know at the beginning?

Karen Peacock: Yeah and I’ll share maybe advice from when I was first starting out in my career in the business world. I think I thought that the best thing to do would be to take the time to learn and then do more smaller iterative things and learn. It took me a little bit of time to realize that it’s critical to take big swings and in the end it’s actually more risky not to take the big swings. When I finally got there it was a huge aha for me and not only has made business life more fun, but I think it makes a huge difference in terms of outcomes so take well informed big swings and quickly learn from them.

Harry Stebbings: Karen, this has been so much fun having you on the show. I think it thoroughly deserves multiple, multiple episodes.

Thank you so much for joining me today, it’s been a pleasure.

Karen Peacock: Very fun to chat with you this morning and take care, Harry.

Harry Stebbings: I mean, my word, what an incredible guest and so many productivity tips and hacks. I want to say a huge thank you to Karen for giving up her time today to appear on the show. A big thank you to Eoghan and Des at Intercom for the intro today as well as Mallun Yen. I really do so appreciate that.

Likewise, I’d love to see you behind the scenes here at SaaStr. You can do it on Instagram @hstebbings1996 with two b’s. It would be great to see you there.

As always I cannot thank you enough for your support and I can’t wait to bring you a very special episode next week.

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