Colin Nederkoorn, CEO of Customer.io: Navigating Growth and Leadership

uh today I’m excited to welcome Colin Neer corn founder and CEO of customer IO to our podcast um excited to have you

today Colin yeah excited to be here um one of the things that I was really

excited to hear more about as I was kind of reading about your your background both personally and professionally is uh

one of the things you did that kind of random is you organized a Windows XP on Intel Mac contest and and I was just

trying to think like you know why why did he do this what was the point you know I’d love to hear more about that it’s sort of like a random early career

thing that you did yeah so um if you were for for those of us who are around

uh way back when there was this period of time where Apple was transitioning to

um a new architecture and they were switching to Intel processors and when they released the

first computers that were running these Intel processors it wasn’t yet possible

to run Windows on on what looked to me and seemed to me like commodity Hardware

right it was the it should essentially be just a laptop like an IBM laptop that

I was that I was using at the time and um I I wasn’t working in Tech I was

working uh in my first job out of school I was working in sales for a shipping

company and I convinced my boss to buy me um a a Mac and I was like dual

booting or I wanted to be able to dual boot the Mac um because I I I preferred

working on a Mac I’d kind of i’ started using it in college and i’ I the my boss

had said yes and so this this Mac was there and it couldn’t run Windows and I

was like uh oh well I convinced my boss I could do my work on this computer how do I how do I solve this problem

and as I looked into it it just seemed like it was theoretically possible uh and so what I did was at this time slash

doot and dig were the were the sites that Tech nerds went to and so I made a

website I bought um winxp on maac.com or something something like that um and I I

put up this website I put up $100 of my own money and offered to collect the the

money into a priv pot for anyone else who wanted to also make this happen and we’d give away the prize right i’ I’d

give away the prize pot to whoever could help us run Windows on the Intel Mac and

um I think we raised $13,500 from all these interested

folks uh and someone solved it it was a bit of a pain uh to to make it work and

pretty soon I’d say like three to six months after our solution was out there um Apple released boot

camp which was their native solution for for doing it uh but it was it was a fun

time and it it really it to it showed me that I could spot an opportunity in the

tech market and gave me the confidence that if I like if I went for it I could make something happen um those I that

that was the the real pivot point where I decided to change my my career and what I was working on from not Tech into

Tech ah super interesting uh so so actually just if I can go back just a minute you mentioned sales at a shipping

company is this like one of those big shipping container companies like you were powering throughout the world or

like what was going on there yeah it was uh bulk liquid like petrochemicals so I

was in I was in Houston and I mean what when people think of petroleum they they

typically think of like gasoline and crude oil and stuff like that and the the sort of the the part of the business

that’s like so important to the to the global economy but the the oil companies care a lot less about is all of these

petrochemical products and so they get they need to go from the refineries in

the US Gulf uh and and in other areas but there’s a lot of refineries in the US Gulf and they need to go to

manufacturing centers uh like like China so we did a lot of trade of these like bulk chemical

products going out to China that would then come back as carpets or styrofoam

packaging or like Plastic Products um and yeah the the my job was um and I was

pretty early in the career but the the career track is is you’re the you’re the broker you sitting between the

petrochemical company and the ship owner to negotiate a good rate to to transport

this bulk bulk petrochemical uh product so super

interesting interesting Niche Niche industry not really my jam but uh I I

gave it a try I learned a lot well I I think it’s it’s sort of an interesting you know pattern of finding like these

cool Niche uh products to work on you know that building your own kind or or I

should say finding a way to launch um windows on Mac um and then

presumably doing other things as your as your career progress so like you mentioned it was a it was a great um

starting point for what you would eventually move into so could you could you talk a little bit more about that early career transition you know so I

noticed for example that you were an IT specialist you mentioned you were in sales your product management your CEO

now um how how have those kind of various roles contributed to who you are now as CEO is it is it huge contribution

has it changed a lot over the years yeah I mean I think my my um my my career so customer io’s other

than being um an intern customer io’s the largest company that I’ve worked for

so I think that being in working primarily in small companies you you

wear a ton of different hats and um one of the things that that I learned even

in that even in that first job where I was ostensively higher to do sales we had blackberries at the time and uh I

convinced the company to move or to set up a a server rack in the office and we

you know installed like Microsoft Exchange and there was all this stuff that I wanted to learn about and and so

I found a way to like give me the opportunity to learn it and help the company solve a business problem um and

so that was the like it specialist hat that I got that I got to wear um because

I wanted to and because I I sort of said hey I I can do this um

let’s let’s build a server rack and and I think that that’s that’s been my experience like when when I got my first

product manager job it was really just because I was in a co-working space and

there was a team of rails developers that needed someone to interface with

the with the client because the client was a bit of a pain and they’re like well if we get this Colin guy in there

he’s he’s pretty good at talking to people so yeah um he can just get the

get the requirements from the client and uh talk to them and um and then we can

just focus on doing you know writing code and delivering stuff for them right

so see it seems like a pretty common theme at least that I’ve seen amongst my engineering friends and peers from

startups that desire to talk to customers sometimes is just absolutely

non-existent they just don’t want to do it ever uh pretty interesting yeah and so I

I think like I I’ve done so many different things I’ve done you know I did support I’ve written code I’ve

really anything that needs to be done in a small business especially a small

technology company I’ve probably done that role at some point I like uh there’s there’s a blog post out there

about our first logo for customer IO which I was like I can do that and I

shouldn’t have been doing that but uh amazing well it it’s interesting because

I I feel like you know uh and we’ll we’ll get into some of your you know the in roots of customer IO and some of the

roles you’ve performed as CEO but it kind of seems like there’s two parts of what I’m understanding you’re hearing

from you it’s like a desire and constancy for Learning and then also like an a willingness to to feel

uncomfortable discomfort and pain you know talking to customers where maybe the engineering team might not want to

um going through the hassle to figure out how to boot Windows on a Mac all these kinds of things that are just annoying so you know I’d love to hear a

little bit about um you know customer IO for example where I think he started it in 2012 is that right yeah that’s right

okay so and like had had you experienced a problem at some prior company that was

like man I really got to go out and figure this out or you know what what was that founding origin Batman story

like for you yeah I mean I think the when when you look at a lot of a lot of startup

founding stories there’s the the Hollywood version of the story and I don’t know how many of these Hollywood

versions of the stories are the actual stories but we never never quite had that that version of the story I think

my my co-founder and I were working at a venture funded startup in New York and

we both really liked working together we wanted to start our own thing and we began a process of trying to figure out

what’s what was an opportunity that we could we could go after um and both he and I he I think he he more than me but

he was really interested in um analytics and big data and sort of do doing

collecting data about what people are doing on a website and so he had a he had a product before customer IO which

would just show you a live data stream of people visiting your site and what they were doing um and it was really

through the process of talking to prospective customers that we heard a bunch of times hey I don’t I don’t need

another Analytics tool I’ve got five of those but instead of showing me user

Behavior if you could help me change user user Behavior that’s really valuable to me that’s like

transformational to my business it makes me more money makes me more successful like that’s valuable so we heard that a

couple times and said kind of scratched our heads and said well hold on a minute if we’ve got all of this user data

coming in we know what people are doing what if we then added a rules engine on top of that and said if people do this

and they do that but then they don’t do this we can send them an email to nudge

them to do that and if we if we can do that then maybe we can deliver more revenue for a

company and maybe we can change us user behavior and help them be more successful and so when we we started

pitching that idea to people and there was a lot of interest uh and and so we just kind of

kept pulling on that thread but it wasn’t and and then in retrospect when

we looked at our company that we were working in and and we we could then sort

of say oh yeah we have some of these problems like our content for the emails

that we’re sending the the welcome email and um onboarding emails they’re all buried in the code of the application

and hey that is kind of annoying to um not enable and empower the our marketer

to change that copy and have to have that go through the the product development process every time one word

needs to be changed in the welcome email and so we were able to sort of fit our

solution uh in in customer IO to problems that we had in the business we were in but it wasn’t like oh man like

we’re sitting around all day and uh thinking about these problems in our business and had a Eureka moment about

how customer IO could solve it and then went and built that business it wasn’t didn’t quite work out that way okay no I

I I think I especially love um one of the things you mentioned was um the the

pain and the difficulty when it comes to like having to change a word or a phrase

or a hyperlink there’s so many parts of a website an app an email that come back

to I need to wait for my developer team my engineering team my product team to prioritize it and it’s like your your

product has eliminated so many of those steps um which I which I think has been great and I think there’s a lot of other

products out there that um I’m thinking back to 2016 I remember I asked our engineering team hey could we get and

this is for a different company company called parse but we asked them to type new signups into Salesforce and they’re

like uh we don’t want to do that it’s not cool so so we ended up just using zapier to like you know plug it in and

since I’ve used customer iio to do the same thing into Salesforce in in our account um but I think that’s a that’s a

pretty important part of your business um had you also thought about you know like uh maybe maybe the founding story

was more typical I think actually probably of how most companies find their Roots um they thought it was an

awesome awesome idea and they went after it but how about you know in terms of what you you hope to accomplish along

the way like were you thinking ah I’m working at a VC company I want to build a massive Mega DEA unicorn where you

like I want to build something that I can work with my partner on and just be excited by every day what what’s it

what’s it look like for you I think that our our initial goal was

to I think our yeah so the the initial goal was just to replace our salaries

try to figure out how could we make I don’t know around 250k to replace our salaries and then

and then probably a little bit more in in and live in New York City and um I

think that that that was the goal but our initial expectation was we’d probably fail and have to move and have

to get real jobs again um but we’d have it would have been a hugely valuable

learning experience that would then make us more you know more more value more

hirable uh it would increase our salaries at the next company that we we would work for because we had gone and

like tried to start a company but I think our expectation was pretty low and

then every time we reach the next Milestone we

reset okay we we achieved this we achieved we got to break even we got to

one million AR we got to 10 million AR and we’d sort of look up and say

uh hey where where can we go from here this and I think like every time I’ve looked I’ve looked at the business

there’s there’s more there there’s more we can do for customers there’s um more

scope to the product that uh we could add to create more value uh and I think we’re not not every

business is going to be like that but we’re we’re fortunate that there’s just always more to do right right for sure

um one of the things that I I had read about was this perspective that you had around you know you mentioned working

for a VC company or VC backed company I should say um you you mentioned that customer iio didn’t really fit very well

into that sort of bootstrapped or or VC funded path tell me a little bit more about that like is that an important

distinction I’d love to know more about it yeah I mean when so we we were fortunate I think by starting the

company in New York and I I don’t know what things are like these days but I imagine the the ecosystem you’re

starting a company and probably still matters um but we we’re fortunate in that we had a ton of support we had a

lot of Angel Investors around and so it wasn’t too hard for us to get some

initial money into the business and after after that first year

I started talking to a few VCS uh and we even put together a deck

to raise a series a um and and I I think the thing that I ran into was so if you think about what

I said a couple minutes ago where we were really just like looking a few feet in front of our face yeah we didn’t have

this billion dooll vision for the for the company and what it would become and so I had a I had a really hard time and

and you need that in order to convince uh VCS to invest and I had a

hard time helping them believe in the in the future prospects of the business

because I didn’t I didn’t know what they were at that point um and so it didn’t make sense for us to go down the VC path

I think like part of it part of it was what we really needed more than money was time we needed time to explore time

to build the product time to do like customer development and really understand our our market and what

problems we were going to solve um and and so yeah it didn’t end up working out

we got uh a bunch of from from folks that I pitched to which I think was really great for us and it forced us to

really figure out and double down on on making the business uh successful on its

own rather than trying to sort of and and I think the way that I think about growing the business is that we’ve we

set our sites on like the the next thing which isn’t too far ahead of us and so

if you’re if you’re doing doing like big fundraises with VCS those step those steps up are massive they’re really far

away the Milestones are really aggressive and you have very little room for air and so the path that we took the

The Next Step wasn’t as far away there was a lot more room for error we can

kind of meander our way there instead of having to go in a straight line really fast and um it enabled us to build the

company more slowly deliberately and the fortunate thing is with the SAS business

you you know you’re you’re really building you you can sometimes build a ton of momentum over time just adding

more mass and adding more customers and I think of it like a snowball rolling

down to Hell Yeah but yeah first first you had to push it sort of to the top

right and then eventually you got it yeah um I love that analogy that’s that’s pretty cool um we’re you know

like looking at some of the uh the early parts so so sounds like you know um I

guess at least in the VC world as as those folks and the types of companies are there non-traditional but for most

most companies how you guys approached it was talk to customers build a product get Revenue build the business and sort

of iterate um you’ve probably made a lot of uh lot of decisions over the years are there ones where you look back and

you’re like man I I wish I had never made that decision or you think that one decision was critical and key like are

there any of those kinds of thoughts that you have yeah I mean I think I think there’s a couple there’s a couple of decisions um

one I’m I’m proud that we launched as early as we did uh I I look at the what

our product looked like when when we launch and I don’t think I would do that today and I don’t I also don’t think the

market would accept what we launched with as our V1 I think the the bar for

every SAS product is just a lot higher than it was uh 10 12 years ago and so if you’re a

new SAS founder like that you you know you really need to be very good to get any attention today um and then I think

like the as far as decisions we made that I would do differently I there’s

nothing I would really change but I there’s one that I’m really I’m very curious about um we made this decision

in 2014 to build a fully distributed company and

the the other path there is what if we stayed in New York like I I moved from New York to Portland Oregon um we then

started hiring people anywhere in the world um and so the the the path we

didn’t take was building a very collocated company all in a city like

New York um I don’t know that we would have survived but I’m curious like what

what would the company have looked like in that in that version of reality yeah I think that’s a pretty

interesting one um have you have you found that I mean

actually maybe just to step back had you worked in a remote environment before or is this like first time just kind of

like made in voidage yeah it was it was the first time uh I i’ done a remote

environment and we tested it out on like I think for a month everyone was working

every you know there were three or four people in the company and so for a month everyone was working from a different

spot uh so we tested it out like that and then went all in on it okay interesting

so you know I’d love to know if if if you’d be open to sharing like what do you I mean maybe not so much like the

pros and cons because I I think like those those ones are a little bit more obvious but you know you guys have been

remote since effectively 2012 um you’re a significant company in terms of employees and revenue and a great

product uh what what are some of the things that you do that might be a little different or a little weird uh or

unique that help you stay aligned and motivated um we We’ve ran remote company at zeit and sometimes personally I I

find it tough to you know work alone to be motivated to go out into my office and and just be there uh anyway so I’d

love to hear how how do how do you keep your team motivated how do you stay motivated how do you get alignment all those kinds of

things yeah I mean I think um I’m I think most of the folks that that work

in our company skew slightly introverted maybe less so on the on the sales side but um a lot of

folks in the company like working remote and find that to some degree if they

were around their their colleagues all day every day it would probably be draining for them and I I think I would

include myself in that in that bucket and I I like the fact that even as our

company gets bigger my experience of the company is very is largely the same I

don’t I don’t feel the size obviously there’s new new people to meet um which is exciting and new you know new cities

we have employees in and and all that stuff um and and you know we one of the

things that I think I we we saw early on so if you think about a a collocated

company where you the company goes from like one floor in a building to two

floors in a building all of a sudden the water cooler conversations are happening

at two different water coolers right like there’s there’s this physical barrier um that’s preventing

communication within this organic communication and so in a in a distributed company the formal lines of

communication have to be clearer and and more well- defined and you hit these

issues much sooner like um like this example of like

the company going from one floor to two floors um those are the things that those are the types of challenges that

you have to like find the formal ways of communicating establish those like more

Awkward or corporate rituals so that um everyone in the

company stays stays aligned and so I don’t know that we do anything out too out of the ordinary you

know we have a a whole company meeting every every month the departments in the

company so there’s like two 275 280 people in the company now and so

we uh the the whole company meeting is less frequent and then there’s more

regular like department and team meetings so that folks are spending time with the with the people that they um

connect with or that they work most closely with um yeah nothing I saw I saw a

LinkedIn post uh I can’t remember I think you had rehar it it was uh maybe

your head of com Marketing sales whatever at a big dining table bunch of customers and I think I think your

retweet was sort of or share what whatever was something like you know looks like somebody’s missing um so H

how do you how do you think about like meeting customers seeing customers talking to customers you know because

like in a remote world I guess it would be pretty easy to pull yourself away

even as you described maybe you’re an introvert or you are rather you are more introverted how do you make sure that

you stay engaged specifically with customer customers then yeah I mean we’ve been in the early days I had a lot

of email exchanges with with our earliest customers I think the in the middle period of the company um I

definitely drifted away from from folks uh but a lot of times I’ll interact with

customers on social media um and we started we’ve started to do events which people seem to really

enjoy and they everyone’s excited to connect with other folks who have their role at another company and so the the

events that we’ve been doing have been going great and I I attended one of them

in Chicago and we’ve got another one another one coming up soon that um I’m

looking forward to it attending as well and so I’m trying to trying to be where our customers are and do it in in a more

efficient way um but yeah I I find that like hearing hearing folks talk about

how they’re using our product is like really energizing for me it’s not it’s not training uh every once in a while

there’s the uncomfortable unhappy conversation uh that with with someone

but I mean those are those are far and few between yeah I I think too I’m sure you’ve noticed this even the painful

ones lead to those Eureka moments of like whoa what what were we thinking or I can’t believe that’s broken you know

um cool well I love that I love that you’ve continued to stay engag with your customers um totally a different

direction but um I saw that you guys recently Rebrand um you know I think rebrands are pretty

significant they take a lot of work I you know I’m curious like I I don’t remember having seeing a prior Rebrand

so love to hear what was the sort of thought process behind it what were you hoping to accomplish you know uh is this

more for you more for the team the customers how how do you view it yeah I think so the the way that I’ve thought

about um the I I think about like the the marketing capabilities or the marketing

side and then the capabilities of the product and you really want those to be

closely inbalance or you want the the marketing promise to be just slightly

ahead of where the product is today um if those are two out of whack then

that’s not then you’re under optimizing the company right if you’re if your marketing is so far ahead that you’re

promising all of these things that and you’re painting a vision of the future that the product is so far from

delivering on then all these customers get disappointed um that and on on the

flip side if the product capabilities are like so far ahead of how you present yourself to the market then you’re not

getting credit for all of the good work that you’re doing and I felt that a couple of years ago the the product was

or it was maybe a year and a half ago we had gotten to this point where the product capabilities were ahead of of

the way that we were talking about ourselves to the market and we weren’t getting credit for all of the good work

we were doing and so in a head-to-head against some competitor people were picking the the competitor who may be

less capable than us because of what they perceived um based on the the brand and

the website and how we portrayed ourselves to the market and so when I hired our CMO Jason one of my asked to

him was to help me tell a better uh like better tell our story to our customers

and and Prospects and um we wanted to not look

like all of the competitive set we wanted to look a little different and

hopefully refreshing uh and make it easier for folks to pick us among among

competitors and you know I think so if you asked who was it for I think it was

for me it was for our team it was for our existing customers and our future

customers uh and I think like I’m really really happy with with how it turned out

um and I think it it just better better portrays us as we want to be seen to to

the market cool I think that’s that’s such a great way to describe it as uh being ahead of the product positioning

you know uh pres presenting selling all those kinds of things that’s that’s super cool and obviously as well there’s

sort of that aspirational side of just being a brand that feels good exciting hopeful all those kinds of things um

well depending on what you want out of it at least um okay so maybe maybe you know two or three other questions but or

two other questions but um you you’ve been leading a CEO for basically over

plus or minus a decade you know we’re 2024 started 2012 um you’ve you’ve

probably changed as a leader as you know uh as a CEO over that period um is there

anything that like you’ve really thought and reflected about like man I can’t believe that I used to be this way or I

really feel like I can do this now like what are some of the big changes that you see from a leadership lens or or you

know when you pull out your set of leadership CEO skills yeah I mean I think the so the

the way that I think about leadership and my responsibility to the team is there’s um

there’s the opportunity that our company has and I my job is to turn myself into

the person that the company needs for this stage and to capture the

opportunity and so the things the tools that I use as a CEO change over time and

the skills that I’m focused on developing are changing over time um as

we progress through these through these different stages as as a company

um I think like the the things that I would do early on um like having you know uh one on

actually so there there’s some tools which I still use which I still find are helpful today I think like connecting

with people in the in the in the team on an individual level is really important

and we have this we we now have my there’s there’s the folks who report directly to me and then there’s the next

level of management who reports to them think forming a relationship like removing the barriers as much as

possible so it’s not like Colin said something and then someone then needs to translate what I said into a mandate for

someone else to translate what I said into you know something for an individual contributor to to understand

I would I think as we’ve grown what I still try to do

is give people enough of a sense of my voice and my what’s in my head so that

um ideally people in the company can understand how I’m thinking about things

and um my approach to to running the business and that’s I think that that’s

one of the ways that I try to I try to keep us align but like the the tools will change the goal is always the same

we want an aligned company where everyone is rowing in the same direction and people know what we’re working

towards um but the way we accomplish that it keeps evolving that’s super

interesting I I think that’s great especially how you framed it as like sort of be who you need to be at the time um but it also sounds like that

consistent message of hey we’re going this direction I need everybody comeing this direction and then kind of you’re

engaging everyone along the way um one one maybe like one just last last quick

question is um you know going back to your sort of formative Roots starting the company um is there any advice

whether it’s conventional traditional or unconventional advice you’d give to folks who are looking to something like

you did or follow a similar path from you know sales to

CEO yeah I mean I think um there’s the I think the the the

advice that I would give really like any anyone starting a company is pick your

Market well I think we were I I I thought about this a little bit when

when we started but we were so fortunate to have picked the email marketing and

marketing automation Market because it’s it’s a massive Market the The Tam that we have is huge we we also manag

to um pick a part of the market that was growing not shrinking and

um I I think that the that’s the that’s one of the biggest things that you

cannot change later and once you go down the path it’s really hard to pick pivot to a new um or different different

market and so that initial decision more than your technology stack or who your

co-founders are if you pick a good market like you can solve a lot of the other problems if you pick a a small

Market or a tough Market to break into all of those things are are you know

near impossible to overcome beautiful beautifully said um

well Colin it’s been great talking with you and thanks for sharing some insight and thought to stay with us yeah thanks Scott see you