How HubSpot got so big

Published: Wed, 11/19/25

Updated: Sat, 11/22/25

November 19, 2025

TOGETHER WITH

Can you believe it’s already the middle of November!? Feels like just yesterday, we were wearing shorts, waiting in line at Starbucks with someone breathing too close to our neck. Bring back the summer heat with this week’s issue, where we’ll look at the history of HubSpot, share a Sales Fail about discovery, and give some advice to a rep who’s being treated like customer support. Enjoy!

NUMBER OF THE WEEK

Referred customers generate 16% more in profits compared to non-referred ones.

Source: TrueList

SALES ROUNDUP

Here’s what’s happening in the sales world this week:

A 60-year-old man accused of pointing a gun at a door-to-door salesman and threatening him this summer has reached a plea deal. The salesman alleged that Robert S. Peters followed him in a truck, pointed a handgun at him and threatened that if he returned to Peters’ neighborhood, he would be “dead.” Peters has alleged that the salesman was harassing his wife. Prosecutors will recommend that he be sentenced to two to six years in prison, suspended for three years of supervised probation. You can read more about it here.
A Florida couple accused of going on a racist rant against a door-to-door salesman is scheduled to appear in court on the charges. Twenty-two-year-old Antavis Johnson says he was going door to door selling solar products when a couple came out of their house and began shouting racist remarks. Explaining what happened, he recalled, “A lot of racial comments, you know, they told me they’ll hang me if I come back." According to court records, Steven Wiley and Cheryl Ann Pyle face assault charges for “unlawfully threatening by word or act to do violence.” The incident happened back in July. You can read more about it here.

FEATURE

"Hubspot TV" by stevegarfield is licensed under CC BY-NC-SA 2.0.

The Origins of Inbound: The Early Days of HubSpot

When Brian Halligan and Dharmesh Shah met at MIT in 2005, the two weren’t thinking about building a massive software company. They spent most of their early conversations dissecting why buyers were behaving so differently from the companies trying to sell to them. People were finding answers on blogs, forums, and search engines long before a salesperson ever got involved. Many sales teams hadn’t adjusted to that shift, and the gap grew bigger each year.

Halligan had watched this happen firsthand while working in sales leadership roles. Shah had a running commentary on the subject through his popular blog, OnStartups. Their perspectives lined up: buyers weren’t hiding; companies just weren’t looking in the right places. That simple observation turned into a business plan, and in 2006 they opened a small office in Cambridge under the name HubSpot.

Building a Company Out of an Idea Buyers Had Already Adopted

The early product was basic. It helped companies publish content, capture leads, and track what people were doing on their websites. The software wasn’t flashy, but it matched real behavior. The more interesting part was how HubSpot proved its own thesis. The blog, the ebooks, the beginner guides became the engine that filled the sales pipeline. Reps spent their days talking to people who had already read ten blog posts, downloaded something, or watched a webinar.

For a lot of reps, this was their first experience with inbound sales. Instead of dialing through a list, they opened their CRM to find prospects explaining their pain points through form submissions. It created a rhythm that other software companies eventually copied: educate first, close later.

Growing Pains and a Playbook Taking Shape

By 2010, HubSpot was no longer a small experiment. More prospects had heard about “inbound marketing,” and the sales team now had to explain detailed funnel concepts that many businesses hadn’t used before. Pipeline reviews included more data than most SMB teams had ever seen. Reps were trained to walk through conversion rates, blog performance, and landing-page testing with the same seriousness a traditional SaaS rep used for product demos.

The company’s culture at this time was fast, young, and demanding. Some employees loved it, others didn’t. But the pace helped HubSpot scale quickly. Funding rounds followed. The offices were filled with recent grads, career-switchers, and sales hires who bought into the idea that they were building a new kind of go-to-market machine.

The IPO and the CRM That Redefined the Company

The turning point came in 2014. HubSpot went public, which gave the company resources and visibility, but the far more important shift for sales teams was the release of HubSpot CRM. This product changed who the company spoke to. Before the CRM, HubSpot mainly lived on marketing budgets. With the CRM, the sales team now had a reason to talk to revenue leaders who had ignored the company for years.

The Dan Lyons Episode and an Unwanted Spotlight

The company’s momentum hit an uncomfortable moment in 2015 when former employee Dan Lyons released Disrupted, a critical memoir about his time inside HubSpot. The book painted the company as chaotic, age-biased, and obsessed with growth. What happened behind the scenes made the situation worse. A senior executive allegedly attempted to gain access to the manuscript through improper means, eventually losing his job and prompting an FBI investigation.

This episode followed the sales team for months. Prospects asked about it in demos. Longtime customers brought it up in renewals. HubSpot had to answer questions about its internal practices at the same time it was trying to mature into a public company with enterprise aspirations. It didn’t derail growth, but it forced a level of internal discipline the company hadn’t needed before.

Remote Work and the Flywheel Era

In 2020, when sales teams suddenly shifted to remote work, HubSpot became one of the systems that actually worked in the new environment. Reps relied on email templates, call logs, video-meeting notes, and CRM tracking to keep deals moving when in-person selling disappeared. The company emphasized the “flywheel” model during this period—a way of describing the loop between marketing, sales, and service that felt more natural than the traditional funnel.

The Current Chapter: Unifying Revenue Teams

Over the past few years, HubSpot has focused on consolidation and automation. AI now appears throughout the CRM, from email suggestions to forecasting notes. Reporting has become central to how leadership teams operate inside the platform. The product’s direction has shifted toward giving revenue teams one system that doesn’t require a full-time admin to maintain.

Why the Story Matters for Sales Leaders Today

HubSpot’s history mirrors the shifts many sales teams experienced over the last two decades. Buyers became self-directed. Marketing created far more influence on the pipeline. CRMs had to become usable or salespeople ignored them. And companies learned that revenue operations work only when every team shares the same information.
HubSpot didn’t create those trends, but it aligned itself with them early and adjusted quickly as they evolved. Its trajectory shows how a sales organization can grow when it studies buyer behavior, adapts internal processes to it, and keeps adjusting the product to reflect how companies actually sell.

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Warning: This book will not make you successful. But it might keep you sane.

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MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

At their peak, how many salespeople did encyclopedia publisher Britannica employ?

A. 38,500
B. 44,000
C. 1,900
D. 2,300

SALES FAILS

Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).

I sell consulting services to deep-tech companies, meaning some of the prospects we deal with are absolute experts in all manner of electronics, software, chemicals, and so on. We have to carefully filter them to make sure we can actually help with their industry, and we also get our fair share of crazies reaching out to us.

One time, I was training a new guy and my boss told me to pick an inbound lead with irrelevant technology, and have the new guy schedule a Zoom call, and watch quietly from the sidelines to provide feedback after. I arbitrarily picked a company called "Advanced Fashion LLC" and took a very brief scroll through their website to confirm they were not in our ICP (they design and manufacture luxury clothing. Definitely not our ICP). I instructed New Guy to go through the typical discovery questions and then politely let the prospect know it wouldn't be a good fit due to lack of technology. Not the best way to actually do discovery, obviously, but the point of the exercise was to really get New Guy comfortable on camera.

We got on the call and started going through some of the standard questions, and before I knew it, the prospect was telling us all about how he invented an advanced sensor for industrial environments, and that he's already had major success selling it to the military. Obviously, this had just turned into a very relevant call, and New Guy was nowhere near equipped to handle it. I was about to jump in when New Guy said something like "We won't be able to help with fashion design, so I'm not sure this will be a good fit." (Again, totally not his fault. I told him to do that. There was no way he could have known and it was definitely me who dropped the ball.)

The prospect looked straight into the camera, visibly angry, and asked, "Did you guys do even an ounce of due diligence before this call? All you had to do was Google my name and you would have seen all the press releases about my new sensor. Or better yet, maybe actually read the lead-intake form I filled out to get on this call. Seriously, I've never seen such a lack of professionalism in my life. Have a nice day, gentlemen."

After he hung up, I apologized profusely to New Guy and felt like an absolute moron for the rest of the day. Moral of the story: Don't judge a company by its name, and do a bit more research beyond just scrolling through the website.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- November 2025

WORTH A PEEK

Sales can be tough on the mind. So how do you avoid falling into a sales depression when you’re not hitting your numbers? This question was posed by a Reddit user, and there are over eighty comments with some useful tips. Check out the conversation here.

ASK THE QUOTA

Want to submit a question and be featured in our advice column? Click here. (Don't worry, you'll remain completely anonymous).

Dear Quota Team,

I’m an account manager for a logistics software company, and one of my biggest clients treats me like their personal help desk. Instead of submitting tickets or emailing support, they send everything directly to me: billing questions, training issues, onboarding tasks. The guy even asked me about a password reset! I’m trying to be helpful because they’re a major account, but I’m losing at least half a day a week doing work our CS and support teams already handle. How do I redirect them without coming off as unresponsive or risking the relationship?

Buried in Chicago

Dear Buried,

You don’t lose clients by setting expectations, you lose them by becoming a bottleneck. Redirecting them isn’t unresponsive, it’s the only way to support them properly. Start by framing it as an upgrade, not a boundary: let them know the support and CS teams can solve issues faster and track them better than you can alone. Then loop those teams into every request until the client adjusts. You’ll still be their point of contact for strategy and relationship work, but the day-to-day tasks need a real process. Good luck!

Quiz Answer: D. At their peak, Britannica employed 2,300 salespeople (You can read the source article here).

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Today's email was written by Ken Kupchik, Erica Furgiuele, Steve Rado, and Emily Hill.

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