Ep. 183 – Boomi COO, Chris Port

Our guest today is the COO of Boomi, Chris Port.

Chris is responsible for the support, services, success, and strategy functions within the company. Chris led the Dell acquisition of Boomi in 2011 and was responsible for the company’s integration and growth post-acquisition.

Previously, Chris was a General Manager within Dell Software’s Systems Management Business Unit, where he was one of the first team members when the organization was formed. Chris brings a range of experiences to Boomi, with his career spanning software, corporate strategy, corporate development, operations, and finance.

Chris was also a senior manager at Kurt Salmon Associates, a global consultancy focused on the retail and consumer products sectors, and spent a year living abroad in Japan. Chris holds a Bachelor of Science degree in Management from Georgia Tech and an MBA from Duke University.

In This Conversation We Discuss:

  • Needing to be the smartest for your role vs needing access to the information needed for your role in today’s modern age
  • What lessons Chris learned when buying a small company and how to get acquired easier when selling
  • How Chris accelerated Boomi’s growth 
  • How to work cooperatively with the bigger corporate organizations 
  • How to utilize the customer advisory board 


Connect with Chris Port: LinkedIn 

Boomi – https://boomi.com

Connect with Cameron: Website | LinkedIn

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Our guest in this episode is the COO of Boomi, Chris Port. He is responsible for the support services, success, and strategy functions within the company. Chris led the Dell acquisition of Boomi in 2011 and was responsible for the company’s integration and growth post-acquisition. Previously, Chris was a General Manager within Dell Software System Management Business Unit, where he was one of the first team members when the organization was formed.

Chris brings a range of experiences to Boomi with his career spanning software, corporate strategy, corporate development, operations, and finance. He was also a Senior Manager at Kurt Salmon Associates, a global consultancy focused on the retail consumer product sectors, and spent a year living abroad in Japan. Chris holds a Bachelor of Science degree in Management from Georgia Tech and an MBA from Duke University. Chris, welcome to the show.

Cameron, thanks for having me.

I guess it makes sense now why you are based in Austin, the fact that you were working with Dell. Is that what brought you to Austin?

That is what brought us here many years ago. It has been a great ride.

It feels like a pretty booming city. Is all the news that we are reading accurate? Is it one direction like all the traffic coming into Austin, and no one was leaving?

That’s what it feels like. It has changed in our nineteen years. What we are seeing now some people feel like it’s the “peak.” If you go and look around construction and look at a lot of the companies, whether it would be Tesla. If you’re ever in Austin, I strongly suggest taking the toll road and looking at the new Gigafactory. It’s awe-inspiring to see but you look at all the construction and companies that are now, instead of moving divisions here, setting up shop in terms of headquarters here. It feels like we may be on the tip of the iceberg in terms of growth but it’s a great time to be in Austin.

Going back into your background, when you did your MBA many years ago, what was it like coming out of that MBA and into the business world, and do you think you still use a lot of the tools that you learned back in your MBA now? If so, which ones are you leaning on heavily?

For me, business school was a bridge out of consulting. I stuck to my guns. I’m mildly proud of that. A lot of people go to business school to get into consulting or banking. It was a bridge for me. The skillsets when I think about it, I never looked at business school necessarily as what I would call academically rigorous in the sense of when coming from Georgia Tech.

I think about the course load I had and what that meant. It was a different experience for me coming from high school to that. It was a shock to my system in terms of the academic rigor that lasted for the better part of four years. To me, business school is more about life rigor because there are so many things you can do in a day, whether it be studying in your course load but also all of the networking opportunities, and all of the different clubs. All of the different companies that are coming to campus on a given day to have a discussion with students so that you can learn about those companies and they can learn about you, etc.

Business school is more about life rigor because there are so many things you can do in a day, whether it be studies or your course load, but also the networking opportunities with the different clubs and companies coming to campus on a given day to discuss with the students.

In a given day, there is 36 hours worth of things you could do in a 17-hour day. You’ve got to prioritize. To me, that is by far the skillset out of everything that I learned. Case studies and thinking through how, and watching how other executives thought through business cases, whether they be financially, marketing, sales or product related, all of that comes to bear.

You get this great broad swath of different ways to think through business problems from different lenses, which to me, was invaluable. The network I built at the school and beyond was invaluable but ultimately, it was learning, “What are you going to attack in a given day that optimizes the day?” You know better than I do, given your background but there’s no lack of things or no lack of opportunities to focus on it a day. My challenge is, “Where do I make the most?” That was probably the biggest takeaway from business school that I’ve leveraged throughout the last many years.

You are not old but you are older in that. When you were at university, the internet was just opening up, I would guess, correct?


You were still in the education phase, where we needed to be the smartest people in the room because we couldn’t access the information. Whereas nowadays, it seems like we no longer need to be the smartest. We need to be connected to all the smartest. Do you see a shift in the people that you’re hiring inside of Boomi?

That’s a great question, and the answer is yes. You look for people that understand how to access information in a digital world that are much more tool-centric and digitally savvy. We probe on that but I still think that another thing is the ability to, at least in my lens, in my purview is people that can synthesize and take all of that information to synthesize and then make business decisions.

That is a unique skillset that you have to search to find. In this job environment, I’ve never seen a job market as we are seeing now, at least in technology. It is incredible. Finding that skillset, A) Is getting tougher, and B) It’s getting more expensive because it’s a candidate’s market. To me, it’s a great perspective back in the day, who you knew, and we would steer a lot at your background. That’s evolved to get much more tangible and give me a real perspective of the toolsets you are familiar with, how you get at data and how technically savvy are you. That becomes more imperative every day.

I want to go back to the Dell component and will fast forward into talking about the candidates, interviewing, and recruiting as well. I want to go down that rabbit hole with you. When you were with Dell, what were some of the key lessons and the key growth for yourself that prepared you to now be the COO over at Boomi?

You asked when I was in school. You got to remember. I was there literally during 9/11. Here we are on the precipice of the twentieth anniversary. That was the start of my second year. A unique time to be in business school. Beggars couldn’t be choosers. For me, what I was looking for was simplistic. It got basic fast because you had firms rescinding offers. If you remember, this is Enron evaporating to a large degree when you think in the grand scheme of it overnight. It’s a unique time to be in the job market.

For me, it was simple. I’m looking for something that gets me out of consulting. I didn’t want to be on the road. I was newly married and thinking about a family. I wanted to have some balance in that sense. I needed something that kept me on that steep learning curve because that’s what I loved about consulting. I loved everything about consulting in terms of the job. I loved the pace. I loved being around smart humans all day, every day. I loved being challenged. I loved new problems, even though I was focused on consumer products and retail.

Every company was a new problem that you were trying to solve, and I loved everything about it. I hated the travel and the fact that you never owned anything at the end of the day. You move on to the next client. I needed something fast-paced that kept me on that learning curve, and that’s what drew me to technology. It was that simple, and that’s where I focused. My recruiting efforts were on technology firms, and that was a good time.

A lot of those firms were going through changes given that time but you could argue that the precipice of this hypergrowth phase that came off the ’01 and ’02 lull accelerated from there. What Dell’s done for me is the people that we’ve acquired. I have been part of small acquisitions. Boomi was 40 people when we bought them.

I always laugh when you say that Dell is an “entrepreneurial culture.” When people ask, “What’s the culture like?” It’s entrepreneurial. It’s like, “Can’t it be? 60 billion, 70 billion and now 90-plus billion and 100,000-plus people. How can a company like that be entrepreneurial?” What I would argue is that the person at the helm is arguably one of the greatest entrepreneurs of all time.

The constant threat throughout my entire career at Dell is that there’s always this willingness to challenge everything and how we become better. That’s why M&A became an easy part of the DNA to accept M&A as we started to go through that acquisition binge that ultimately led me to Boomi but challenging everything. It also had a willingness. I wouldn’t say it’s formal but for people to move around.

SIC 183 | Boomi

Boomi: The person at the helm of Dell is arguably one of the greatest entrepreneurs of all time. There’s always this willingness to challenge everything and how to become better.


If you wanted to go do something, I went from hardcore operations, literally working in a factory when Dell used to do manufacturing here in the States. My next job was at Dell Ventures. I don’t know if there could be much more of a 180 but that’s far foot and then I went into a sales segment, did what I will call pseudo sales roles, and then went back into corporate strategy.

Dell has a tolerance for all of this. It’s a unique company. I’m not saying that’s the fastest path to glory in terms of promotions and all that fun stuff and career, as you think about a career. I’ve skated towards challenges versus getting fixated on becoming an operations VP or a Finance VP or something like that. I’ve always tried to focus on two things like hairy problems. I like solving problems. It’s what keeps me going. It gets me up out of bed in the morning. It’s what excites me. It’s the greatest job I’ve ever had. It’s about solving problems.

This is critical for anyone who wants to be a COO of a larger organization. They need to be able to work in all these cross-functional areas. They need to do the hairy problems in all the different business areas and not only stick into one silo, which is interesting. When you are in a smaller company, that doesn’t tend to happen as much. Dell was arguably one of the hottest tech companies on the planet back in the early 2000s.

I remember when I got my first Dell, and I could throw my IBMs out the window. I was super excited. That was around 2001 as well. You are at Dell and jump over from Dell to a 40-person company. Let’s talk about the acquisition before I talk about you moving over. When you led the acquisition of a 40-person company, first off, what was it like? What lessons did you have in buying a smaller company that our readers can learn from? Also, if you are a smaller company looking to sell, I’ve got four of my clients that are working with an M&A firm to sell their companies. What lessons can you get them on how to get acquired and how to make the transaction process easier from both sides?

I would say that on the buy side, I had the opportunity to study a handful of acquisitions that Dell had done in the SaaS space that, for a myriad of reasons, didn’t go according to the business plan. I had some things to build upon but my two biggest takeaways were simple. This was 40 people moving inside a 100,000-person company, and we needed to incubate. It was, “Incubate, don’t integrate.” That was the tagline, and every acquisition is different. That’s something I’ve gained a perspective on over the last few years of doing M&A. Everything is different but this one was to incubate, don’t integrate. Leave it alone. Leave the stack alone.

In terms of the software stack, we are not going to try to shove their software stack into the Dell stack. A) It was a stack built for hardware, not SaaS. B) Built for a multibillion-dollar company, not for a 40-person company. Also, don’t break it apart. Leave it all up under a CEO/GM, and let’s incubate this. Two, let’s get it on a glide path with a strategy that sets the stage for the first 18 to 36 months.

That’s what I leaned into because it’s all about momentum from an M&A perspective. When you buy a company, how quickly you get out of the gate is so imperative to longevity and early success. Those were the two things on the buy side. On the sale side, I’m certainly not the person. I’ve never sold a company, so I’m not savvy enough. I would tell you a couple of things, and I don’t think there are any big secrets here but being able to demonstrate product-market fit is imperative.

Being able to demonstrate product-market fit is imperative. People underplay it, but we shouldn’t lose sight of that.

What is your cultural fit with the buyer? If the buyer is serious about the longevity of the asset they are buying the technology to the company, whatever it may be, then that cultural is imperative. People like to underplay it but to me, it’s like, “Don’t lose sight of that,” and that goes both ways. It’s a seller’s market, so your friends are probably in good positions depending upon what space they are in because money is still cheap.

They have an opportunity to find the right fit for them, and I would tell you, in two of the M&As I’ve done, it was a competitive perspective. While the dollars meant something, if you want to think about a “bidding war,” at the end of the day, both of them, meaning the other side of the table, who do they feel had a better fit, and where would they feel comfortable trying to grow this company?

Again, that’s very company-dependent. Sometimes owners want to exit, and they want to get out. They are looking for the biggest dollar but at least when we’ve thought about it. We do acquisitions so much in technology. It’s who am I acquiring? Who’s going to be part of the team here? We are looking for people that want that and want to be a part of something, at least for a while.

When you were doing the acquisition, did you know that you were going to end up as a part of the leadership team of then integrating, innovating, and growing the company?

Yes. It’s what I wanted to do. It wasn’t a given. I was in the corporate strategy group. I led the identification and, ultimately, due diligence of Boomi but at the time, Dell had propped up this role called the integration executive. I had a friend and a couple of people that I knew had done it. It interested me but to be honest. It was also one of those things.

We do the acquisition, and I raise my hand. I want to go do this, and everybody that’s in my mentor network is telling me, “Absolutely, don’t do it. You are zigging when you should be zagging. You convinced the ELT, the Executive Leadership Team of Dell, to buy this tiny asset. You won. Go take advantage of this. Lean into your strategy experience.” There were promotable roles and a couple that had been offered to me but my perspective was like, “I’ve effectively done strategy now my entire career. I need to go operate because I ultimately want to be a GM. I want to be a GM and run something at some point.

Now, I’ve academically studied the software, if you will. I’ve never been inside the guts of a software company. I want to do this, roll up my sleeves, and figure out what this is all about. I threw my hat in the ring. Ultimately, it was the integration exec for Boomi and probably the best decision I’ve ever made in my professional career, hands down, because I got to see everything right out of the gate. It’s dog years when you are in the middle of an acquisition.

We are going to talk about the whole growth from 120 when you got into approximately 1,200 people. I’ve got one final question on Dell that’s always intrigued me. I’m curious if you had any visibility to it. Back in the day, Kevin Rollins was the COO to Michael. Did you have any visibility to the Kevin and Michael partnership because they were strong for a period, and then they were volatile? Did you get any visibility of them as an amazing partnership?

No real insight. That was exactly when I joined corporate strategy. Dell was effectively making the transition from that partnership when Michael stepped back in to take the company over. I have zero insight into that. Where we’ve now gone, that would have been a few years ago. You look at the growth trajectory and how the company’s evolved and become much more diversified over time but no real insight into there. I was in corporate strategy, so I was a front-row seat for the whole thing as it evolved, and Michael stepped back in, which was interesting.

They were one of the partnerships that when Brian and I were building 1-800-GOT-JUNK, we were trying to find some strong CEO, COO or the yin and yang, and they were one that was identified for us. We started to look at a bunch of different ones, and they were one of them. Let’s talk about Boomi. First off, what does Boomi do? Can you give it to us in layman’s terms, and then let’s talk about the growth that you took the company through?

Simplistically, we are a connections company. When you think about Boomi, it’s integration. It’s middleware, and we connect applications, which is our typical starting point for companies. I know that could be a database. It could be a myriad of things but connecting Salesforce to SAP. You need those two systems to talk. You need your CRM to talk to your ERP, and we are the glue that makes that happen in a very modern SaaS-like, high-time-to-value, and high-productivity way.

Drag and drop. A great example would be a company like Peloton that brings us onboard to effectively stitch their ERP to their CRM as they are going on this crazy growth trajectory. Ultimately, it starts to leverage us but then we grow out of that. We do things like EDI. It’s super old technology. We modernize your EDI stack. It now allows you to connect to your partner network, and then we grow into things like API and allow you to connect to individual end users in a very governed way. It’s all ultimately about connections, whether it’s applications, data, people or processes. It’s all about connections in a modern high, productivity way.

You’ve grown the organization now from 120 to 1,200 people inside Dell. What do you think are the core reasons why you were able to get that growth that didn’t involve the money that Dell was giving you? You can’t grow because they throw money. You can also fall apart if that happens. Why were you able to grow successfully?

We’ve had an industry-leading product now for effectively the entire time that Boomi has been a part of Dell, and certainly, since Gartner’s released their magic quadrants, we have always been in the top right. We’ve got a great product-market fit. We’ve got an amazing product and an amazing product organization, and we’ve always leaned into making sure we are ahead of that integration curve. Like any space that’s insanely competitive, there’s always someone new coming in but we have this amazing opportunity.

SIC 183 | Boomi

Boomi: Just like any space, software technology is insanely competitive. There’s always someone new coming in.


Candidly, we are now on the precipice of a lot of these macro trends that we were betting on 5 or 7 years ago are now coming to fruition, whether it be the explosion of data, the explosion of SaaS applications or do you want to call that the hybrid environment explosion? You are now talking about a mass labor shortage that feels like it’s a wave that’s about to crash down on the heads of a lot of people like me in terms of finding people to be able to do things.

Now, you’ve got to think about the tool sets you are selecting that require a lot of people to maintain, and that plays right into Boomi’s sweet spot of high productivity, call it low labor in terms of when you build out a middleware stack. A lot of this is about product market fit. There was an investment angle to this because when Dell did the divestiture of EMC and Dell software, they excluded one asset there, and that was Boomi.

It’s because of that we were given a lot more visibility, which can be good and bad but it also highlighted what the growth opportunity was, and it did open up the OpEx, the spending envelope. We were given a lot more investment, which did allow us to start because, at the end of the day, the bulk of our investment is in people, and how do we grow a proper global sales organization? How do we grow a proper product and development organization?

How do we grow these organizations to focus on what is an immense global opportunity for us to go from 150 to 1,200, and we are well on our way to 1,400 to 1,500 by the end of this year? At the end of the day, a lot of this is about the product and how we’ve met all of these customers’ needs across the globe now, moving north of 17,000 customers. It has a product that solves a very acute problem, which is growing and exploding in a direct and high-time-to-value way.

I’m curious how it is working with some of the big organizations that Boomi’s had to work with. My girlfriend was the Head of Engineering for Salesforce inside of Ticketmaster. I know that she used Boomi there and then also at another company, Internet Creation, where she brought Boomi in. What’s it like for your team working with these big organizations? How do you prevent yourself from banging your head against the wall?

I have always been in the entrepreneurial world but I find corporate hard to work with. It seems like there are a lot of people that will say yes to projects because they don’t want to say no, and then stuff can take so long. You have all these needs from external forces. Any lessons for our readers on how to work with bigger organizations successfully?

We’ve learned our way through it like most companies, particularly in the SaaS or the B2B space has gone from 41 to now 1,200 plus people. We started very much call-on-call. I wouldn’t say mid-market but call it the large mid-market, and I have now moved upwards to disrupt a lot of those legacy players in the integration space. It’s a very typical play for a disruptive SaaS provider.

We’ve grown our way into those large environments like a Ticketmaster but I would tell you, we’ve done a few things. We’ve maintained our ability to have good relationships with customers. We don’t relax. We have a customer advisory board and these are huge logos that everybody would know that sit on our customer advisory board.

To a person, they all say something, “One of your products is great. We love your product. It allows us to do things and be insanely agile. We can do 10 projects in the time that would take us to do 2 with your competitors.” We love all that but the other thing we love about Boomi is your good people and, A) Your product does what it says, but B) You do what you say. We try to maintain that ability as we’ve scaled, and it’s challenging because you have to put a process in place to go from hundreds of customers to 17,000-plus customers to go from 150 to 1,200 team members.

You’ve got to have a lot of processes and technology. It allows us to now scale to the next 17,000 customers but we’ve tried to maintain that customer relationship and we do that out of the gate by leaning into our success equation and making sure that they have the resources out of the gate. Even if a sales maker thinks that, “I don’t want to introduce professional services because it could be a hurdle to me getting the deal done. We try not to relax on a methodology.

Once we know what that customer is trying to get done, we try to be very dogmatic on, “Here’s what you need to be successful. Trust us. We’ve done this 17,000 times now. We know we have an equation, and you always have a successful professional with you but it may include leveraging this partner who’s good at doing this with you. It may include having our professional service team help you do this.” Support is always underneath that but it’s trying to be as dogmatic as possible.

We are getting better every day. We are still not perfect at it and never will be but trying to be dogmatic on what the customer needs to be initially successful. For 60, 90, and 180 days, it is so imperative to have longevity with us. That’s most SaaS companies but if we can make this successful early, we are going to have a long journey with them, and we are both going to grow together. We try to be dogmatic out of the gate.

I love this idea of the customer advisory board. I remember Michael Dell used to read the tea leaves. He used to listen to all of his customers and read all their comments. How do you work with a customer? I had a franchise advisory board and all the franchise companies I’ve built but how do you listen to the customers? What do you bring to the customer advisory board? How do you use that tool or that system you’ve put in place?

We lean into them. They are all under NDA but we share the gory details of Boomi with them. We don’t leverage it as a place for affirmation. We leverage it as a place to like, “Give us blunt feedback.” We will do a few things. We will throw complex issues that we are dealing with and how we are thinking about moving through them. We will talk to them not about an asset but about spaces.

Don’t leverage the customer advisory board as a place for affirmation. Leverage it as a place to look for or give you blunt feedback.

These are spaces that we are contemplating moving into from an M&A and build versus buy type of discussion. What would you think if Boomi came to you offering this? We will never focus on space. We will do a little bit of a menu of, “We will bring in three spaces. One of them we know in the back of our mind we are focused on and likely have a company that we are focused on, if not multiple but tease it out from them. Get their perspective of like, “If you came to me with that solution, it would be of interest or I don’t think I would look to Boomi to solve that problem for me.”

You’ve dragged them into operational things for me but we are very purposeful and like, “This isn’t an audience to make sure we are getting affirmation that we are doing everything great. We will bring in the actual metrics and say, “For me, how are we doing from success and support? How is this going?” Have individual discussions but we try to leverage them. They would tell you that it has been a valuable experience for them too. They are very crisp in their feedback.

I love that you bring them some of the big hairy ones too, and you open the kimono. You’ve talked a couple of times about how hard the labor market has gotten and how tough it is to find great people. I’m curious about what you are doing at Boomi to attract great people. Secondly, this is a bit of a bizarre question that I’ve never even asked before. What would a smaller company do to attract people when they are competing against Boomi? If I was a 40-person company in Austin and trying to hire the same person you are, what do I do to get them so that you don’t because the small companies can’t pay what the Facebooks and Googles can pay?

I don’t want to arm my competitors with too many building blocks but for Boomi, we are trying to do a couple of things. We are trying to lean into what our culture is because, in my opinion, it is such a huge differentiator. When you look at our attrition, a lot of people and companies are looking at attrition data as you are seeing the Great Resignation happen across the world.

The pandemic has accelerated that. Once we get back to some, whenever and whatever, it looks like some sense of “normalcy,” I do think that will help slow some of this down but we are trying to lean into our culture and who we are. It has been such a strong point for us for so long, and attrition data has always been incredible relative to our competitive set in a very good way.

We don’t see a lot of attrition, and even in this period of somewhat elevated attrition, it’s still based on all the benchmarks we are staring at world-class. We are trying to lean into what Boomi is, and what you are joining is a key differentiator. It’s because what we are finding is like, “The money can be good. Equities and another thing, as we get on the other side of this transaction, we are excited about having Boomi equity but at the end of the day, a lot of the companies who offer packages start to look the same.

You all roughly start to learn what everybody is offering each person. Now, the next question is, “How do I prove to you that this is a great place to come build your career?” We are trying to lean into, A) It’s a market leader, but B) there’s something bigger that’s happening here. I have never been part of something like this. I don’t take it for granted. These opportunities don’t come along that often. Having done a fair amount of M&A, a lot of people say we are almost at a $100 million ARR balance. We are almost at a $1 billion valuation. It’s amazing that every single SaaS company you meet at times seems to be almost at those benchmarks.

We get blown by all that stuff, and it doesn’t happen that often. We think we are on the next evolution of this whole thing as we get on the other side of the acquisition to go to another whole year of growth when you look at these macro trends. Trying to lean into that story, and when I think about differentiation, to me, there is a reality, though. There are people that want to go work at 40-person companies. Forty-person companies are different from 1,200-person companies, and I will fully acknowledge that.

We try every day to, “How do we keep that entrepreneurial vibe going? How do we keep that edge?” Every company, to some degree, works through that in its own way as you grow, which is, “How do you keep that edge? How do you remain paranoid candidly? How do you continue to disrupt and constantly look at yourself as “the little guy,” to go punch above your weight?” To some degree, it’s like, “If someone is looking for that small environment, they are going to go there, and if someone is looking for something that’s a little bit more at a scale that’s years ahead of that, then that’s a different environment and opportunity.

I like that you quoted Andy Grove there, “Only the Paranoid Survives.” You didn’t quite but I think that’s where you were thinking. Is Dell going to spin Boomi off into its own public company at some point?

Dell’s announced the divestiture of Boomi. We are still in the process of closing. It was announced in May 2021 that we were bought by Francisco Partners and TPG, two of the preeminent private equity firms in the world focused on technology. That deal will close sometime in the next few months. We are still part of the Dell family, and it has been an incredible ride but I would tell you that we are equally as excited about what the next phase holds and now working and partnering with people that all they think about all day, every day, is software.

Everybody that we are working with on that side of the fence now, that’s all of their experience both from a deal side as well as an operational side. I’m so excited about this next part of the journey and now being part of a portfolio of companies from the Francisco Partners and when you look at the TPG, their growth equity arm, which is what we are part of. You look at these portfolio companies and their world-class software companies. Also, learning from them about how they’ve optimized their growth. I’m excited.

How about your growth? Where have you optimized your growth as a leader?

I would say to some degree, and when you’ve gone from 150 to 1,200, we are still at that size of what I will call we are all player coaches. I have what I will call a pseudo-board meeting. I have been knee-deep in Excel models and was combing through Gainsight, trying to understand some stuff about some key customers. I’m in the weeds of moments, and I will be in the boardroom to have a discussion at that level. For me, what I’ve probably learned the most, to be honest, is being a leader of people, and what does that mean? How do you go?

When I got here, my part of that 150 was probably 40-ish, and my organization now is north of 400. How I’ve evolved and candidly put a leadership team in place over the years that’s allowed me to scale. I was reading your blog with Harley Finkelstein from Shopify, and he didn’t say this but there’s a reality. I don’t care who they are. Maybe once you’ve done five of these gigs, you could say this but we are all learning on the job.

I’ve certainly never led 400-person teams prior to Boomi but the one thing I’ve learned is that I’ve got to almost scare myself with the people I hire in the sense that I now have people in place, whether it’s support, professional services, success or sales ops. Whatever it may be, these people have forgotten more about those functions than I will ever learn, and that’s a great thing because they scare me every day with their ideas and how they think about the business.

I’ve learned how to push them and, hopefully, push the business forward. They’ve allowed me to scale on a completely different level than I would’ve thought possible when I got here. It’s because when you first become a leader, and those teams grow, you are trying to maintain that touch with everything that you had your fingers on initially that, over time, it’s an impossibility. Having people that are so good at what they do it’s allowed me to scale. My biggest growth area by far is how I think about my team and how we think about leaders in general at Boomi and building out a world-class leadership team.

SIC 183 | Boomi

Boomi: Be a leader of people who scare you every day with their ideas and how they think about the business. Learn how to push them, and they will help push the business forward.


I love that you recognize this. I’ve always said that we are sixteen-year-olds trapped in adult bodies, and it always feels like this is the biggest thing we’ve ever done every day. It is a little bit bigger. I met Harley when they were only about a 50-person company. I went into their offices in Ottawa, and it has been incredible to watch their growth. I got one final question before we get to sign off. I want to go back to you graduating from Duke University. What advice would you give the early twenties, Chris Port? What would you tell yourself that you know to be true now but wish you’d known when you were a little younger?

To some degree, it would be to articulate who you are and what you want to be. I don’t mean what you want to be in twenty years. I’ve always struggled with that but always have some type of three-year window that you are always thinking about and stick to it as much as you humanly can. It gets difficult as you get out there. When you are in business school, the money that the consulting firms or the banks throw at people, even for me, it was incredibly difficult to say no and to come back and say, “Why did you go to business school?”

Over time, that only happens not every day but it certainly happens at all these different moments in your career. There’s an “easy” task but to go up and get bigger roles, those “promotions” and all that fun stuff but articulate and understand who you are and where you are trying to go. Ultimately, that’s the way to maximize if you are short of a handful of people that you had to dig or entrepreneurs that know how to cash out and do that type of thing.

If you are not that person, and I certainly wasn’t, it’s articulate who you are, and that will optimize that 20, 30 or 40-year career that most of us have as we think through it. I would lean into that statement myself twenty years ago because it’s one of those things I constantly remind myself of. “What exactly am I trying to get done here?” Forget money, team, title or any of that. It’s like, “What is getting me up every day to be excited and solve problems.” That’s what I try to remind myself of and fall back on. It’s a hard thing to stick to at times.

I love that you’ve got another three-year vision out in front of you as to where you are heading now with Boomi as you make this next transition. Chris Port, the COO for Boomi. Thanks very much for sharing with us on the show.

Cameron, I appreciate it. Thank you for your time.

I appreciate it.


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About Chris Port

SIC 183 | BoomiExperienced general management and strategy executive with broad experience. Ability to create a game changing strategy, implement the strategy and grow a business. Demonstrates proven leadership and team-building abilities. Track record of solving complex, data-intensive problems; influencing strategy; and creating innovative solutions to drive significant quantifiable results.

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