Inside Customer Success HubSpot Stephen O'Keefe
With 20,000 customers worldwide, HubSpot is the world’s leading inbound marketing and sales platform, transforming the way businesses attract, engage, and delight customers.

We sat down with Stephen O’Keefe, Director of Customer Success, to discuss how Customer Success has evolved at HubSpot over the last 7 years.

Can you give us a brief overview of Customer Success at HubSpot, and of your responsibilities?

I started in HubSpot in 2009 and I’m now coming up on my 7-year anniversary. When I first joined the company, we had about a hundred or so employees and around a thousand customers. There were 4 Customer Success Managers at the time. Back then we simply divided everything by 4 and that’s just how it worked.

Since then, we’ve grown a lot as a company and I’ve grown as an individual. We started to have a more thoughtful segmentation about our customer base, and I started working with our corporate customers — those who tended to have the most advanced use cases. Eventually, I began leading a team of Customer Success Managers in our corporate group, and now I lead the mid-market group as well — the biggest chunk of HubSpot’s customers.

Inside Customer Success HubSpot Stephen O'Keefe

How did you get started in Customer Success and what was your path into your current role?

I got started in this industry back in 2004, shortly after I graduated from college. My background immediately after college was actually working in political campaigns; there, I started to observe some interesting trends with regard to how political campaigns organized and raised money. And I found some interesting software companies that did this sort of thing. This was back before SaaS companies were given that acronym — they were called ASPs (Application Service Providers) back in the early 2000s.

I found a company called GetActive Software and they worked with large, national, non-profit political campaigns, higher ed, public broadcasting — that kind of thing. I helped them raise money and build their membership lists. And I did that for about 5 years in Washington, D.C. then I found HubSpot. So I moved back to the Boston area where I was originally from — it seemed like a very natural transition.

What I liked about HubSpot, in addition to being a growing business, was that it was very much mission-oriented. We really want to help companies transform the way they do marketing and sales.

“What I liked about HubSpot, in addition to being a growing business, was that it was very much mission-oriented. We really want to help companies transform the way they do marketing and sales.”

Inside Customer Success HubSpot Stephen O'Keefe

How is your team structured at HubSpot and how have you seen that structure change over the last 6 years?

I’d say that overall, with growth has come specialization. I alluded to how things were 7 years ago: 4 CSMs looking over 250 accounts. Over time we started to segment customers based on the number of employees or customer type. With the customer we sell to directly, we segment based on the size of the business. If you come from a small business, say with 1-10 people, you’re serviced by our SMB team. If you’re a company that has between 10-200 employees, you’re you’re serviced by our mid-market team. And finally, if you have over 200 employees, you’re you’re serviced by our corporate group. We continue to refine on this model every year.

Those groups have evolved over the last 6 years, and we’ve continued to refine our playbooks – and the profile of the CSMs we hire – to better align with those segments. This segmentation model has allowed our team to be fairly agile based on the customer inflows.

Inside Customer Success HubSpot Stephen O'Keefe

Would you say that agility is the biggest advantage of your team structure?

We’re able to be agile, but at the same time, have some level of specialization.

Let’s use our corporate group as an example. If you’re dealing with a large company, you may have more experience in dealing with situations involving legal, security, or highly technical integrations. On the other hand, if you’re dealing with a very small business, it’s more about them getting found, getting leads, and getting customers, the importance of identifying the right keywords and buyer personas. The conversations you have are specific to the persona you are serving.

What’s the biggest challenge of your team structure? How do you address it?

With thousands of customers and a growing line of products, how do you scale the group while continuing to provide a high level of service? This requires us to look beyond just the size of the company purchasing HubSpot but also at the specific products, or the combination of products, they’re purchasing, as well as where they are in the customer lifecycle. We spend a lot of time thinking about this.

Inside Customer Success HubSpot Stephen O'Keefe

What does the culture of Customer Success look like at HubSpot?

We’re known for culture here. Our co-founder Dharmesh has created the widely popular HubSpot Culture Code. It talks about some of the key pillars of our culture. In Customer Success, we’re always solving for the customer. There’s sort of a pyramid — you solve for the customer first, the company second, your team third, and then lastly, yourself as an individual. We put the customer first and that has never changed, even when we became a public company.

Even though we’re a bigger company now, it’s still very much a meritocracy — everybody, to some extent, has a metric that they are trying to hit, and we are very transparent about people’s metrics and what we are all working on. This allows everyone to stay in sync and really showcases our top performers.

“There’s sort of a pyramid — you solve for the customer first, the company second, your team third, and then lastly, yourself as an individual.”

What does a typical day look like on your team?

An individual CSM could be managing anywhere from 80-175 accounts, depending on the particular set of customers they are aligned with. Their day would be a mixture of proactive and reactive: on the proactive side, we strive for the team to have very strong quarterly engagements with our customers; it may be a quarterly business review, to help the customer understand the latest and greatest features of the software and how they can be applied to their particular business use case. So ideally you’d have about 3-5 high quality customer interactions per day.

At the same time, there’s also the reactive stuff you manage. Everything from providing copies of invoices and receipts to answering product questions to reviewing blog article headlines and copy. When you develop strong rapport and trust with a customer, they go to you for just about everything.

Inside Customer Success HubSpot Stephen O'Keefe

How has your user base changed since you started at HubSpot?

The user base has gotten a lot more sophisticated over time. They get what inbound marketing is much more so than they did 7 years ago. They don’t need you to tell them about the importance of blogging or content marketing — they get it. It’s more about, “How does this fit into their overall business strategy? The campaigns that they’re running? And what’s the return on their investment?” The average marketer is now more technical too; they want to tie all the pieces together and HubSpot allows them to do that. They want everything to work seamlessly.

What blogs or news sites are you reading at the moment?

I have two young kids (including an 11-week old) at home, meaning I don’t get to do much personal reading nowadays. But I will say I have my Feedly filled with Customer Success blogs. I like to read Seth Godin because his stuff is very focused on Customer Success themes. I spend quite a bit of time on the Customer Success Forum on LinkedIn. It’s a high traffic group that I get a lot of value from. I also subscribe to a number of customer success oriented blogs.

Inside Customer Success HubSpot Stephen O'Keefe

What is the most powerful part of your process?

We’re pretty good at ensuring that we’re having quality engagements with each of our accounts. Using our CRM, we can quickly see, “Okay, based on where they are in the lifecycle and their needs, who are the customers who we need to be talking to? When was their most recent quarterly business review?” We can also measure things like how quickly we got back to our accounts on an inbound email.

Also, we have a tight alignment with folks who do onboarding. We have an implementation specialists group within our services organization that is responsible for the first 90 days or so. We partner with them very closely during that time to ensure that the customers are set up for success. We often do a joint kick-off call and a joint onboarding wrap-up call as well.

How do you think HubSpot’s processes differ from your competitors’?

We’re very focused on the business impact. While it’s important to us that the customer sets up and uses certain features, that’s not good enough. We want to make sure the software is driving the desired business outcomes.

Inside Customer Success HubSpot Stephen O'Keefe

What role does Customer Success play in developing the overall business strategy at HubSpot?

We always have the voice of the customer in mind, and having a tight feedback loop with the Product team is key. If a customer cancels, then we make sure we all ask ourselves, “What was the root cause of why this customer cancelled?” We try to surface that information so it eventually gets back into both the products and services offerings, so that another customer won’t have to deal with whatever issue it was that caused the customer to cancel.

“We always have the voice of the customer in mind, and having a tight feedback loop with the Product team is key. ”

What types of metrics do you watch closely?

We look closely at a few metrics, the first one being MRR (Monthly Recurring Revenue) retention. To use some round numbers, let’s say you start the month with a $100,000 of MRR, how much do net out at the end of that month? That’s made up of 2 things: The customers you upsell, and the customers you lose. We look carefully at the raw customer retention and the things that cause customer to be successful and cancel. If you don’t improve this number over time, you’re just filling up a leaky boat. The upsell rate helps you understand the success are you having at introducing your customers to your new products and features that could help them. In customer success, I’d say our primary focus is on pure customer retention. If you get good at making your customers successful and retaining them, that will eventually beget revenue retention and an increasing upgrade rate.

Inside Customer Success HubSpot Stephen O'Keefe

How important do you think managing your customer relationships has been to the success of HubSpot’s platform?

It’s been incredibly important. In the early days of HubSpot, before 2009, we didn’t have customer success and retention was a problem. We layered in customer success and retention improved right away. On top of that, we made some major investments in the product that improved retention even further and fueled a ton of growth over the last several years.

How can you tell that you’ve made your customer successful?

There are leading indicators and there are lagging indicators. The lagging indicator, of course, is retention. What’s so hard about Customer Success is getting those leading indicators. Because it’s really hard to convince a customer that’s cancelled that they’ve made the wrong decision. The leading indicators for us are pretty straightforward: Are they using the product and is it producing the desired value? We have some metrics to say that if a customer uses the product for a certain amount of time, they’re generally pretty healthy and more likely to renew. We’re always trying to get more sophisticated in how we look at this.

Inside Customer Success HubSpot Stephen O'Keefe

What does success look like to you in your everyday life?

Solving interesting problems. It’s why I’ve been in this role for so long and haven’t switched. I find that the problems in Customer Success are interesting and are always varied. So any day I come into work and get to make progress on a problem, small or large… it’s been a pretty good day for me.

What’s great about this job too is that when you’re an individual CSM in the funnel, the problem-solving opportunities are really interesting. We benefit from having a really interesting customer base: We’ve got customers that sell monkey wrenches and some that make semiconductors and everything else in between. So the problems that these customers have are generally just fascinating. If you’re interested in how businesses go to market and make money and survive — this will be a really interesting job for you.

What’s one piece of advice you have for Customer Success Professionals who were in your position 6 years ago?

Get technical. In my experience, our best CSMs have been the ones that know the product inside and out, and the ones that also have expertise outside of the product. Because at the end of the day, you need to deliver value in terms of helping your customer get set up on the product and using it in a way that helps their business. Any hand off you can prevent (because you know how the product works and can address advanced use cases) is an opportunity to build trust with that customer and help them be successful. Products are only getting more and more technical — so learn your product and get as technical as you can.

Inside Customer Success HubSpot Stephen O'Keefe

Photos by Caroline Alden.
Put together by Mathilde Augustin and Trisha Armeña.