5 scale-up leadership lessons by Brian Halligan, co-founder and CEO Hubspot

Jungle Ventures
Oct 19, 2020 · 5 min read
Brian Halligan, co-founder and CEO of Hubspot

As part of the Jungle Ventures community, our founders have access to some of the most admired CEOs in the world. Brian Halligan, co-founder & CEO of Hubspot & an old friend to Anurag Srivastava & Chris Reisig in the Jungle Ventures team, joined the Founders Assembly to give his point of view on how he is building a company that will make his grandkids ‘glow with pride’ when they tell their friends that grandad founded Hubspot.

Along with his Co-Founder Dharmesh Shah, Brian has not only built a category-defining company with a market cap of over $10bn but also an award-winning corporate culture. They turned a big idea into an even bigger business. A business whose rate of innovation has never slowed since the company’s founding back in 2004. Brian demonstrates that rare combination of curiosity, tenacity & humility we look for in all our founders & it was a privilege to hear about his journey to success. Watch the full video here.

So, what did we learn?

The job is never done

Brian describes Hubspot as an ‘incomplete painting’. A painting that will probably never be finished. He says that for every two steps you take forward you are taking one step back. As soon as he thinks he has something figured out, it breaks. Like any company, Hubspot doesn’t exist in a vacuum. He is constantly having to evolve in order to outsmart new competitors & remain compliant with evolving legislation.

Hubspot’s growth is in many ways down to the Founder’s determination not to settle into the accepted rhythms of a big business. Hubspot’s mission is to help businesses grow better every day, & to achieve this they have had to commit to relentless reinvention. He is convinced that Hubspot must own their planned journey from App to Suite to Platform. His reverence for the product & passion for the customer experience is clearly as heartfelt today as when the company first started. In his own words Hubspot is a ‘Big Start-up’.

Going public is just the beginning

Founders & investors dream of going public. Not just for the financial rewards but for the sense of accomplishment. It is a huge moment in the lifecycle of a start-up &, as Brian pointed out, one of those very few moments in the journey of a successful start-up founder when they get to sit back, take a deep breath & consider the scale of what they have achieved.

In a landmark IPO in 2014 Hubspot raised US$125mn in fresh capital & achieved a valuation of $880mn so it was surprising to hear Brian say he wishes he had done it differently. At the time he & Dharmesh were under considerable investor pressure to go public & the temptation was hard to resist. However the company was in the process of pivoting. They were beginning to place greater emphasis on CRM, a nascent revenue stream within the organisation. The original Hubspot pitch was focused & the business model proven, the new story exciting but lacking the track record.

Especially at a time when public rounds are not necessarily any more lucrative than private markets, Brian encouraged our founders to be patient. To make the move when they are 100% confident in their pitch. But most importantly he reminded us that, whilst the day you go public will live long in the memory, it is the start-line not their finish-line. Founders need to remember this & so do their team.

Culture is how you build a big company

Building a culture is hard work. We know that too often founders are slow to prioritise culture as it is not in their comfort zone & it is mistakenly seen as a distraction from the core needs of a growing business.

It was reassuring for our founders to hear that for Brian it was the same. As unlikely as it sounds given the accolades Hubspot now receives, during the early days of the company culture was almost a dirty word. Brian told us how he was dismissive of the need to spend time codifying the corporate values & or to invest money in enhancing the employee experience. It was only from talking to CEOs a few years further into their journey that he began to appreciate that, especially as the company grows, having a strong culture is the best way to ensure good decision making across the organisation.

Brian recalled how, once he & Dharmesh made the decision to prioritise culture, they didn’t compromise. When they couldn’t find an experienced HR leader they felt comfortable with they didn’t settle. Instead they went to a trusted lieutenant already within the organisation with no HR experience & asked them to take a more analytical approach to culture. What resulted was the Culture Code, a publicly available presentation that every founder would do well to read

Building a new category is not for the faint of heart

Founders always wrestle with how they should communicate their proposition to investors & customers. Are they inventing a new category or simply disrupting an existing one? When Hubspot coined the phrase ‘INBOUND Marketing’ Brian knew he was taking a risk.

‘Not for the faint of heart’ is how he described the choice to tell the world that Hubspot was creating a category. Brian & Dharmesh crafted a narrative that positioned INBOUND Marketing as the good guy to Outbound Marketing’s bad guy, then they took to the stage, blogged endlessly, wrote books & made as much noise as they could to ensure the term stuck.

This time the risk paid off but Brian was quick to point out that he is not in possession of a magic formula for success. When Hubspot shifted into sales software they attempted to run the same playbook & began talking about ‘Inbound Sales vs Outbound Sales’ but neither customers nor investors were buying it. So whilst appearing to be first to market is attractive, it is fraught with danger. You have to be willing to commit most of your marketing money & energy behind telling your story.

Being a CEO is a craft

At Jungle we pride ourselves on helping our visionary founders learn to become skilled CEOs. We encourage our founders to embrace every opportunity to learn & grow. When asked to offer his advice Brian reminded our own Founder CEOs that their employees really care what they think about them.

Brian refers to being a CEO as a ‘craft’. A rare & precious skill that has to be constantly worked at if you are to reach the top of your game. Brian revealed that he often suffers from ‘imposter syndrome’ like any founder but that he uses this as motivation to continually refine his skills as a leader by listening to, reading about & speaking to the CEOs he admires. Critically he also recognises that there are areas where he will always fall short & builds a board around him that matches his weak spots.

Being a CEO is stressful. There are always new problems to solve. Big decisions are taken every day. You need every member of your team making great decisions when you are not in the room. Being able to communicate your vision across the company & build a workplace community that supports it is critical. This is what Brian has been able to achieve at Hubspot & the upsides are evident.

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