As one of the founding members of HubSpot, Jim O’Neill knows SaaS and inbound from the inside out. That’s just one of the reasons the company he co-founded, SaaSWorks, where he currently serves as CTO, has been an unprecedentedly disruptive force in its vertical. 

After growing the HubSpot team from 5 employees to over 1,500, and rapidly acquiring 25,000+ clients after starting with just 10, his success as a business leader earned him recognition as Boston Business Journal’s CIO of the Year 2015.

Jim’s company is the end result of years of high-level expertise and dynamic, in-depth learnings. SaaSWorks enables data-driven decision making at scale by unifying, enriching and segmenting customer data across platforms to provide uniquely tailored business insights that translate into real outcomes and tangible wins.

SaaSWorks helps company solve the fundamental challenge at the root of revenue operations by using the power of data to facilitate rapid scalability by reaching, securing, and satisfying customers in any vertical. 


Jim’s remarkable success was largely enabled by an equally valuable mentor. When he graduated into a stagnant economy during the 90’s, the job market was a barren landscape. Even equipped with an extremely practical technical degree, prospects were slim. 

Jim’s One Away Moment came in the form of a big offer to join a small, 10-person team at an obscure new startup that would come to be known as the market leader in Inbound Marketing: HubSpot

Right off the tail of a failed interview elsewhere, Jim got a call that would change everything. He accepted a part-time offer with gratitude. Little did he know he would eventually become a driving force in the company’s massive success. 

On his first day, his boss assigned him a daunting task and taught him an immensely valuable life lesson he’s help onto ever since.  After spending all day working on a challenging programming assignment that didn’t quite make the mark, Jim’s boss offered the perfect balance of firm accountability and generous investment in growth and success.

“I think most bosses, especially when assessing code by a new grad, would say, “We’ll test it,” and then pass it off to a more senior teammate if it wasn’t right. Instead, he literally sat with me for 1-2 more hours and actually showed me how to code well. He told me what I did right, what I did wrong, and even how the things that I did wrong may have given the right output or could be improved. At the end, I remember him saying very succinctly, “Now, you’ve finished your task.” 

This leadership style is one Jim has emulated with his own companies, and it’s a method I strive towards as well. Holistic assessment paired with the training and skill building required to achieve set goals is the ultimate marker of success.

Top 5 Takeaways From Jim O’Neill

Even though a decent portion of this episode covered Jim’s early career and educational experiences back in the 90’s, there are astute parallels we can draw. Similarly to the challenge Jim faced when he was graduating, even with one of the most practical technical degrees, the current economic crisis due to the COVID-19 pandemic.

Just like Jim’s college peers, this year’s graduates, the class of 2020, have an unprecedented challenge to face as they seek employment with their newly minted diplomas. Whether you’re a recent grad or a professional looking to make a change at any stage of your career, here are 5 valuable nuggets of wisdom to come away with from Jim’s One Away Experience:

1. Even the most practical backgrounds require adaptability in the face of the unknown. As you transition from college into the job market, or from an entry-level or even mid-career role to a better fit, keep an open mind and sense of pragmatism.

2. Embrace unique opportunities rather than holding out for prestige. Why waste more time chasing after the same opportunity everyone elsewants at a shiny, brand-name corporation (where you’ll like become just another face in the crowd), when you can carve out a niche for yourself and stand out where you truly belong?

3. Seek mentors who never let you settle for anything but your best work. From his first day at HubSpot onward, Jim’s boss pushed him to get to the finish line and empowered him with the education and training he needed to get there.

4. Effort and ethics will always natter more than a fancy resume. Prior to HubSpot, Jim’s work experience had mostly been in the restaurant industry, and in roles outside programming. His reputation as incredibly hard-working, reliable, and personally invested in every task within his responsibilities made him stand out from the crowd as the best candidate and made up for prior professional experience in the same vertical.

“My best advice is to take on as much as you’re willing to, watch out for where you could break, and trust that the dust will settle in the end.”

5. In leadership, the simplest and most straightforward approach is often the best. An amusing but memorable anecdote Jim shared with me really illustrates how taking a little extra time to explain what something means is always more helpful to employees than assuming they already know how:

“On my first day, my boss handed me a binder (I laugh at this now because Google didn’t even exist back then) full of terms I didn’t understand. There were all these acronyms I had never seen before. Now, anytime someone uses an acronym, I tell them to “help a friend out.” Don’t just give them an acronym – actually tell them what it means.”

During my conversation with Jim O’Neill in this episode, just like our unforgettable conversation at HubSpot’s INBOUND conference where we first met, I was consistently struck by the profound insights he draws from his experiences. He is a living testament to something we’re always told: the key to success is having a strong work ethic. If you want to achieve your goals, stop looking for shortcuts and workarounds. Start putting in the hard work today, and you’ll begin yielding the results you’re after.

So many important people I’ve encountered throughout the years have left an indelible mark on me and my path, and they all have one thing in common. The pivotal figures who have launched me past the next milestone or helped pick me up when I’ve fallen down have never just been “yes men.” 

The most significant people in my life are always the ones who have pushed me to be better, challenged my ideas to reach that next big breakthrough, and never let me settle for anything less than giving my all.

Even if it feels good or comfortable, surrounding yourself with a room of talking heads or people who pander to your every idea will never bring out the best you have to offer. Seek out great minds with complementary ideas who can help you achieve continuous improvement.

Here are the two questions Jim always asks himself:

  • “Did I give it my all?” 
  • “Did I do my best?

I feel really motivated to start building in these two questions into the extensive model of self-assessment I’ve been building out. Having this as a gut-check will be another excellent resource I can tap into along my lifelong journey of self-discovery, pathfinding, and ultimately, growth.

How Jim O’Neill is Building a Legacy in the Start-up World

With several CTO and CIO titles at rapid-growth businesses under his belt, Jim O’Neill is a leading investor and operator in the startup space. He is currently an esteemed advisor and board member to several notable early-stage, venture and private-equity backed startups. Wherever he goes, success seems to follow; all his past businesses have had successful exits, mergers, and acquisitions by larger platforms. 

Currently, Jim serves as a member of the Massachusetts Governor’s Council for Innovation under Governor Deval Patrick, and is an active Member of the Dean’s Council of Strategic Advisors at Worcester Polytechnic Institute. 

Check out the episode in full at YouTube up top, on Spotify, or on Apple Podcasts. A transcript is included for your convenience below.

In parting, I’ll leave you with these parting words of wisdom from Jim directly:

“You’ll never know unless you try it. You may fail. You may not like it and don’t do it again. If you don’t like something, it’s silly to keep trying to do it because that’s the definition of insanity. If you like it and you want to get better at it, look for those patterns because those do make you a stronger contributor. Continue to specialize to the point where it becomes less exciting. Find your next thing that you know very little about, and then get to be expert level.”


BRYAN WISH: Jim O’Neill and I first met back at HubSpot’s annual conference, INBOUND. I remember going up to you with my friend, Michael. We talked for 45 minutes on the last day. You were so nice. I was like, “Why is this guy giving me so much time and helping me?” I’ll never forget how great this connection was. It was one of the most rewarding conference conversations I’ve ever had. So, Jim, tell us about your One Away moment.

JIM O’NEILL: I think my One Away moment is similar to other stories that people have shared on your podcast. It’s always about someone giving you an opportunity that you may or may not think you had deserved or were worthy of. When someone actually makes such a choice, they may or many not understand the impact that has on your life. 

In this case, for me personally, I graduated college as an electrical engineer in the early 90s. A lot of people don’t remember this, because it happened a little bit ago in history, but there was actually a pretty bad economy in the early 90s. 

When I started college as an engineer, the university I attended was very technical. They talked about having a 90%+ job placement rate. When I was graduating college, that figure dropped down to around 35%. For someone like me who was academically trained to be an electrical engineer, about to enter the job market, that was pretty weak at the time. 

I honestly didn’t know what I wanted to be when I grew up. I put three resumes together. One was in electrical engineering, to actually go build circuits. Another was based on writing computer software, because I was fortunate enough to have taken some programming classes. The third version was designed for getting into technical sales. People thought I was kind of a nerd when I start getting into tech circles.

I was really kind of just floating around without a clear sense of direction. A friend of a friend told me, “Hey, there’s this small startup that is in Newton, Massachusetts, a very small suburb. So-and-so knows the founder. You should go talk to them because they’re hiring a software developer.”

I was pretty nervous because the week prior, I had interviewed for a computer programming job and failed at that interview miserably. They gave me a very basic programming test, and I fumbled my way through it. I didn’t get the job. I’d gone in without a clear idea of:

  1. What I was good at
  2. Whether I could I even do well at such a job, or
  3. In such a bad economy, if this was even going to be a durable job for such a very early stage company 

I got into the interview and fumbled my way through the whole thing. My interviewer took a step back and said “Hey, slow down. Let’s talk through how you approach problem solving. Tell me about the jobs you’ve done.”

Up until then, I had been a short-order cook and a shift manager at a restaurant, amond other positions that were not relevant to me becoming a software engineer. For some reason, he connected some dots and said,

“Hey, how about you show up for work on Tuesday?” (It was a Tuesday after Labor Day). “We’ll see what you can do. We’ll pay you hourly because we can’t afford to hire you full-time.” 

He totally took a chance on me. I eagerly showed up my first day and got there pretty early in the morning. He was kind enough to tell me about the product they were building. Within the first 30 minutes or so, he also showed me the software development environment. In the early 90s, this was nothing like it is today. We’re talking barebones coding. 

On my first day, my boss handed me a binder (I laugh at this now because Google didn’t even exist back then) full of terms I didn’t understand. There were all these acronyms I had never seen before. Now, anytime someone uses an acronym, I’m like, “Help a friend out. Don’t give them an acronym – actually tell them what it means.”

He gives it to me and said, “Just have at it and let me know how you do.” Six o’clock rolls around, the end of the work day. I’ve been doing my best to code, if you want to call it that, for 10ish hours. I sheepishly walk over to him because I am pretty mentally exhausted, and I say, “Hey, I’m going to go home for the day. I’ll see you tomorrow morning.” 

He was so kind. He gave me this nice smile and he’s like, “Did you finish your task?” I’m like, “What task is that?” He’s like, “That document I gave you; did you actually finish the coding for it.” I’m like, “I think so.” 

I think most bosses, especially when assessing code by a new grad, would say, “We’ll test it,” and then pass it off to a more senior teammate if it wasn’t right. Instead, he literally sat with me for 1-2 more hours and actually showed me how to code well. He told me what I did right, what I did wrong, and even how the things that I did wrong may have given the right output or could be improved. At the end, I remember him saying very succinctly, “Now you’ve finished your task.”

He didn’t just throw a bunch of work at me and see if I could sink or swim:

A). He took a bet on me to even hire me 

B). He actually invested 2-3 hours of his time that day 

C). He showed me what success was

I got bitten by the bug of, “Oh wow, this is what it takes to build a product in an early stage company which was not prescriptive. It was not demanding. It was actually very encouraging and a ton of autonomy. I think that was the moment I got hooked.

I always look back at that one day of him hiring me and four days later of him spending the time and investing and coaching me. You fast-forward a year, and that company was acquired by a publicly traded software company that honestly just changed my life. That company grew to multiple billion dollars of revenue. I got to see things I wasn’t even aware of what these things were because I grew up pretty modestly. It changed my life. I’ll never forget that. 

BRYAN WISH: What do you think he saw in you, in that moment, to say, “This is a guy I can put my chips on in the early stages when it really counts?”

JIM O’NEILL: There are two things that are interesting job characteristics, but they aren’t obvious skills for a computer programmer. He was asking me about my prior work experience, even in a restaurant. What I had shared was how they put me in charge of scheduling and shift management when I was in college. I think he could tell that I would take responsibility when it mattered the most. 

The other thing I told him was that I still needed to work at that restaurant while I was doing the coding because I needed the money. I think he heard that I was hard working and not going to take this programming job and just phone it in. He sensed I actually had the level of personal investment and driven to show that I would take care of any task. 

What was funny was after about six months, they did give me a nice raise and hire me full-time. They actually asked me to stop working at the restaurant. They’re like, “You can afford not to work at the restaurant now.” I think people skills, that he picked up, was the responsibility and that I’d be hardworking. That’s what aligned us. 

BRYAN WISH: It sounds like that moment was very profound and it really kind of dictated your future and work ethic for the future. Can you dive into that?

JIM O’NEILL: I think it’s because I came out of an hourly job where you had shifts. Honestly, even decades later, I still have to remind myself that the difference between an exempt employee and a non-exempt employee really does dictate work behavior. I wasn’t aware enough at the time, but by the fact I had been there 10 hours, I was a little bit tired. I could have kept going. 

Even when I went home that night, I kept thinking about the problems I was trying to solve. I think it was the fact that the work flexibility and the work structures were so unclear then that I literally didn’t know how long I should stay at work. It was a lack of awareness. I think nowadays, there’s so much more constructs around that. I didn’t know if I should go home or if I should keep going. 

BRYAN WISH: Let’s talk about Simmon. What was he like as a person? You’re going to go sign up to give your life to a startup at such a young age of your life, when maybe people around you or the more corporate or safe job was calling you, but you took a risk on someone as well. He might have seen something in you, but what did you see in him that said, “I’m going to do this with you?” 

JIM O’NEILL: There are two things and they still hold true today. I still consider him a big mentor of mine. One was the passion he had talking about the product they were building. Facial expressions say a lot on people. He could hardly contain himself about what they were trying to solve and the way he was talking about it. 

He said, “This is a really hard problem. We just won an award. The math behind it makes my head hurt but I’m obsessing on it.” Just how he described the job to me, I was like, “I want to work here.” I love hard problems. I may not care about the award side of it but I sure cared if they’re writing algorithms that are getting recognized, that’s really cool. I think the passion was one.

The second, he’s still probably one of the smartest people I’ve ever met. I think people can measure smartness by academic accomplishments or job titles. The level of depth he could go into on some of the problems they were solving was beyond what I thought a normal manager or vice president would normally go to. 

I think I took this huge risk because he cared so much about the product they were building. The way he worked, I could just tell from the start how much growth was ahead of me. I thought, “Wow, I’m going to learn so much.” Technically, I was extremely excited about working with someone that could talk to that level of specificity in an area that I knew very little about. 

BRYAN WISH: You said he was incredibly smart and could go into things. Was there a way in which he went about learning things, how he absorbed things, and how he educated it back to the team that really impressed you and that you brought into your future work?

JIM O’NEILL: Good ole’ white-boarding. I think he was able to get on a white board and show clearly how to solve a problem. In many interviews, I think it’s often the employer vs. the employee. Luckily, this seems to have evolved over time, but back in the 90s, it was usually pitted against each other this way. Interviews were often very much designed as a test to trick you. That wasn’t his approach. 

Instead, his mentality was, “Hey, I’m going to walk through this algorithm – with me.” He literally gave me opportunities mid-interview to ask questions and give feedback. I think what he was testing for was how I asked the questions:

  • Did I show linear thinking? 
  • Did I throw geometric thinking? 
  • Or, did I not think at all about it? 

I’ll brag on his behalf because he still does some work in the worlds we’re in. He’s written code in 45 programming languages. 

You think about a human that has spoken multiple languages; a programmer in 45 languages is just kind of bizarre. I think this was his way of conveying it to such depth. Showing it by participating in the problem solving versus just throwing stuff up on the board and seeing what stuck. 

BRYAN WISH: It sounds like he has the brain of a robot and computer but the people skills of a very smart person.

JIM O’NEILL: Totally.

BRYAN WISH: Describe the journey and path you’re on after you accepted it. What was that like until that acquisition? Describe the culture that was created around the company up until the acquisition.

JIM O’NEILL: The acquisition happened within a year. A software developer and a team of seven total people in the company; a very small startup. The team comradery around the problem solving, coordination of code, segregation of duties, “You work on this. I’ll work on that.” 

It was actually exhilarating. All we cared about was the customer winning. When I say that, it was back when we were really trying to figure out some unique technical challenges. At the end of the day, everyone cared about the same thing first and foremost:  

“How does a customer benefit?”

It was less about how hard the problem was. Rather, the really important question was:

How easily can the solution be used? 

I think that unique mentality really shaped the company’s course to success.

Secondly, and this was probably a little bit more visible post-acquisition, but just the exposure to every part of the business:

  • Someone has to order lunch 
  • Someone has to pay the bills
  • Someone has to call the customer
  • Someone has to keep the lights on
  • Someone has to keep the servers running

Anyone that’s ever thinking about an early stage company, I encourage them to don’t do the job you’re hired for; do the job that needs to be done and the job that you’re hired for. I think people limit their possibilities when they just do what they’ve gone to school for or they think their role is. At a startup, you got to do everything. I just got lucky. I did everything that was available to me.

BRYAN WISH: What are things you maybe learned about yourself during this period, and even after the acquisition, that maybe happened a lot faster because of the environment that you were thrown into? If you were giving advice to someone right out of college or a couple years into their career, what would some of those things be?

JIM O’NEILL: Part of this answer comes down to character flaws or strengths, depending on how you look at it. For me, I am pathologically unable to say no. I can’t say no to anything. It’s gotten me in a lot of trouble in life, but it’s also been very rewarding. 

If you’re early in your career, it’s a little bit of an extension to what I just said, but I want to be very specific about it. I said no to nothing and I said everything was possible. Now did I know if it was possible or how much work it would be? Absolutely not. 

If there is a massive amount of work to be done and you’re the person that says, “That’s really hard. I’m going to have to work really late. I’ve got a dinner this evening.” I’m talking more startups than bigger companies. I think the people that elect not to just say yes, but to actually over deliver, that is a consideration. Not everyone is going to be willing and able to do it.

I hate to say, but the answer is simple: it’s just hard work. I honestly feel like because I was incapable of saying no and I said yes to everything, I probably made some bad choices on the things I said yes to, but I learned so much. The next time I said yes, it got easier. 

A lot of my teammates rallied with me on that. They also were yes people. The ones that were no people, I don’t think they did as well. I’m not saying that you do a bad job. I’m just saying that if you’re really trying to build a company and you’re trying to learn and figure it out, everything should be possible until its not or everything should be practical until its unnecessary. 

I was a VP in this bigger company within five years. I just kept taking more on. I know a lot of people would say, “I wasn’t given the opportunity.” I’ve learned to look backwards and say sometimes you have to take the opportunity. I don’t mean with politics or positioning. 

If there’s a concrete job sitting there that a company is trying to hire for, who cares about the title? Go do the job. 

You’ll get paid.

You’ll get your title. 

You’ll get all that stuff if you prove you can do it. 

My best advice is to take on as much as you’re willing to, watch out for where you could break, and trust that the dust will settle in the end.

BRYAN WISH: Can you say the name of the acquisition company?

JIM O’NEILL: At the time, it was called SunGard Data Systems. They acquired us and they were about $400 million of revenue in 1994. They hit about $2.5 billion of revenue by the year 2000. They had pretty exponential growth. They later were acquired by a company called FIS which is a world leading financial services/financial software, fintech company.

BRYAN WISH: Now what you’re doing today with SaaSWorks is incredibly interesting with the subscription model and how you built software into that to help companies. As you look back at all these different sets of experiences over the last 15-20 years, what are some of the patterns you picked up on this journey and the relationship between all these experiences when you look more introspectively at the patterns behind it?

JIM O’NEILL: Work is intrinsically hard. That journey leads to the business that we’re starting today. There’s a lot of noise out there with automation, AI, machine learning, and our job is going to be lost. I think when people are losing, I saw this pattern through my career and have been lucky to observe it and get coached and mentored to take advantage of it: people are really good at solving hard problems. 

Sometimes it’s just messy, hard work. It’s messy data. It’s messy people problems. The computers aren’t good at that stuff. My fallback, the pattern that I often revert to, is taking on more work and more responsibility. 

You’ll never know unless you try it. You may fail. You may not like it and don’t do it again. If you don’t like something, it’s silly to keep trying to do it because that’s the definition of insanity. If you like it and you want to get better at it, look for those patterns because those do make you a stronger contributor. 

Continue to specialize to the point where it becomes less exciting. Find your next thing that you know very little about and then get to be expert level. It’s almost like all these mini-careers, I feel I’ve been afforded through people, including at HubSpot. 

Don’t worry about automation. You should embrace it. Let it do the stuff that people aren’t good at doing. The stuff that is really hard and really messy. People should be running towards because we will make it better over time. Similarly, computers will become better and more powerful over time. Everything else is just noise. There’s a lot of noise out there right now especially in the AI/ML space. With SaaS companies, in particular, that’s the business we’re going after.

Building a company is hard, but you got to start somewhere. Stop worrying about it and just do it. You have to get out of your own way.

BRYAN WISH: You said, what’s messy is what people should be running towards. Most people run away from what’s messy. It’s the human side of things. With all the computer and machine learning, it’s never going to replace things we should be worried about with the human touch. 

You have some really interesting skill sets. Most computer programmers, who start out, they don’t really evolve into the people side of things. In your role at HubSpot, where you were the Chief People Officer, you clearly transitioned in a way and it clearly showed when I first met you of just how charismatic and connective I felt our conversation was. What has been the hardest challenge for you as you’ve been on this path and this career trajectory of transitioning out of something where you were a specialist to the whole people side of things? 

JIM O’NEILL: People are emotional beings. I wish we weren’t. When I talked about messy things, people are pretty messy. We’re all messy. We have emotions. We have passions. We have interests. Why I gravitated towards it was out of necessity because, at least in my experience at HubSpot, the company was doing so well. 

The culture was so strong. However, when you start to scale, the messiness of people – when I say messiness, I mean organization, communication, alignment. That stuff gets to be really hard. What I got excited about, and I’m very grateful for that time in that role, was if you truly like problem solving and you’re comfortable being uncomfortable with conversations, most people issues are just problems. 

If you actually can talk through it and also be receptive of feedback, which I always say I’m thick skinned. I’m really not. I’m very think skinned. I put up the front that I’m thick skinned. Once you get comfortable or acknowledge that you’re thin skinned, you can treat programming problems like people problems. They’re logical paths. There might be illogical references or illogical emotions, but if you know the end that you’re solving for, there’s a great expression: Begin with the end in mind. 

If you think about the problem that you’re trying to solve and the end result that you want, then you just try to apply the thoughtful emotional path or skills path or logic path to get there. It’s harder than code. 

People problems are a lot harder than coding is, but they’re probably the most rewarding type to solve because the feedback loop is real time. You coach someone or try to help someone and you might get a highly positive message. You might get a highly negative message. You might get something in between.

If you learn his/her/their reactions, then you’ll know how to put that feedback to the next time. 

People are like code. They’re a little bit less linear, but I do think you can put a problem solving a framework around it. If you’re willing to deal with the “mess,” I think you’ll be extremely rewarded. 

I do think HR professionals have a special gene in them that can handle this forever… I had a couple year window where I did it. I wanted to get back to coding because I did find coding to be more logical, but I think you can apply problem solving framework to any kind of situation people or code and just go through it. 

BRYAN WISH: I like how you said people are like code, just less linear. They just have a lot of messy emotions. Give us a two-minute elevator pitch of what you guys are doing, what the big vision is, and how you’re going to make it happen.

JIM O’NEILL: The tagline is we’re helping subscription businesses and SaaS companies scale more sustainably. Running a business is pretty hard nowadays. They’re very complicated; the rate at which these SaaS companies have to grow at to be successful, the amount of hiring they have to do.

We’re really building a framework and a platform but people led to actually help companies run their subscription businesses better. There’s an altruistic part to it. I feel very blessed in my life. 

If we can help other SaaS and subscription businesses have better outcomes through better operations and better technology, we’d be honored to do that. It’s a pretty immersive business and we’re just getting going, but we’re very excited about it. 

BRYAN WISH: Where can people find you?

JIM O’NEILL: is the website. For me, you’ll find me on LinkedIn, Twitter, and you can email me at JimO’ and I will respond. It might take me a little bit, but I will try my best to get back to everyone.