The unfair skills Kieran Flanagan acquired to go from a B2B creator to a global CMO

Kieran Flanagan

Staying relevant is much harder today than it was in Ogilvy’s time, even though many of us still recall his lessons and use him as an example.

The world is more crowded. More customers and more products than ever.

So how can one differentiate itself?

Why cultivate creativity and innovation

Embracing innovation and testing ideas and strategies is essential for several reasons.

It allows you to differentiate yourself in a crowded market by offering unique solutions and experiences to your customers.

By constantly experimenting with new approaches, you can find new ways to solve problems, address pain points, and deliver value to your audience.

Needless to say that being open to new ideas helps you stay agile and responsive to changing market trends and customer needs.

It helps you quickly identify what works and what doesn’t, allowing you to pivot and adapt your approach.

Someone who’s open to testing ideas and strategies is Kieran Flanagan.

He knows how to make himself stay relevant, drive growth and deliver value in this constantly changing marketing world.

Who is Kieran Flanagan?

He has an impressive work background from working at big companies such as Marketo, Miro, and 10 years in the HubSpot team as a Marketing Director, VP of Marketing and Growth and later Senior Vice President of Marketing.

Now Kieran is an active advisor at Sequoia Scout, Sowork and, and an investor at 8 companies.

Even though you would say that with such a vast experience, with all the investments and advisor role, he could sit back and relax, Kieran’s passion for marketing doesn’t let him step aside.

He’s currently CMO at Zapier where he leads the company’s global marketing strategies and initiatives.

Besides everything I mentioned, he’s also a Top Voice on LinkedIn where he has an audience of 48,315 followers.

On LinkedIn you’ll see him post about all things related to marketing and product-led growth.

If this is all Kieran does, you are wrong.

He’s also a podcaster at Marketing Against The Grain which he launched back in 2022.

And he also has a newsletter called GrowthTLDR where he helps SaaS companies with insight on how to grow their traffic, users, and revenue.

Why is he a B2B creator?

  1. Marketer for HubSpot and Zapier
  2. Marketing savvy
  3. Collaboration Master
  4. Zapier Promoter
  5. Early adopter of AI

A. Marketer for HubSpot and Zapier

As the Senior Vice President of Marketing at HubSpot, he played a key role in helping the company amass 100,000 customers and surpass $1 billion in revenue. 

Kieran was helping with three important parts: with the acquisition for the sales product, the freemium funnel, and with the global web strategy.

Beyond that, Kieran also led HubSpot’s foray into the media industry, paving the way for the creation of HubSpot Media Group and the acquisition of the beloved newsletter, The Hustle.

But what did Kieran and the whole HubSpot team do right that made their product so wanted by all the marketing teams I know?

In an interview back when Kieran was still working for HubSpot, he said that HubSpot is rather unique in the B2B space because 100% of their sales are made from the marketing acquired.

It’s all inbound demand.

It’s either the leads they generate or the users they generate within their freemium model. 

One advantage they had over other similar businesses was that HubSpot had the luxury to think 18-24 months in advance what they can invest to ensure that they will have new sources of growth if the channels they were growing on were predicted to plateau.

They always laid down their growth for the next one or two years, but came up with a list of investments they had to make right from the beginning to make sure they have the necessary growth channels in the next couple of years.

While Kieran was still at HubSpot when he started taking advisory roles for startups, he began talking to Wade Foster, Zapier’s CEO and Co-founder.

Talking to Wade made him realize what successful startups did right as opposed to the others.

It was the focus.

Zapier was focusing on two-three important things in order to grow instead of everything. 

They concentrated to be the best at the things they knew they needed to excel.

So they double downed on making sure they had the right talent, the right focus, and right prioritization.

Instead of doing everything at once and draining themself and having sleepless nights and burn out, they focused on two, three things at the time.

Seems easy, but it’s hard to find what you should put your mind into next when you feel all your competitors are ahead of you.

I did some digging to see if the relationship built with Zapier while at HubSpot had an impact on Kieran’s decision to join Zapier, but I found nothing.

He might have officially joined Zapier in 2023 as a CMO, but he definitely constantly communicated with Wade and the team since the interview I found where he talks about Zapier was from 2019.

Plus, even on his first day at Zapier he mentions that he was always a Zapier fan and that he met a lot of people from the company over the years.

He says that there were three reasons why he made a career switch: likes solving problems across marketing and product-led growth, they were new challenges, and he loved the people from Zapier.

Plus, in an interview he mentioned that he gets bored and he likes to do new things every couple of years.

B. Marketing savvy

If you’re a marketer and you’re not following Kieran, you’re missing out on many strategies and marketing trends.

On LinkedIn you will find out he talks about product-led strategies, about building audiences, or about content production.

Few months ago he talked about the importance of growing an audience as the number one skill people should learn in B2B especially in this creator-led economy.

He talks about seeing creators starting B2C businesses, but he says that soon influencers and creators will start launching software products for better margins.

He gives Mr. Beast as an example who besides creating restaurants and candy bars, launched his software product called ViewStats for better YouTube Analytics.

Speaking of the product-led strategies, Kieran opens up on LinkedIn and talks about what strategies he wishes he could do at HubSpot.

He’s talking about the strategy of “Buy Front Doors, Monetize onto Side Doors”.

This strategy involves acquiring companies with a large user base and then leveraging that user base to cross-sell other products or services. 

He talks about Atlassian’s successful execution of this strategy through acquisitions like Trello and Loom, where they integrate their existing products like Jira into the acquired platforms to upsell to the user base. 

He emphasizes the importance of finding the right acquisition targets to execute this strategy effectively.

He also talks a lot about creating content and how to produce quality content.

He talks about the fact that to be a good marketer today you need to have good content skills.

But to write good content you should follow ‘The Double Cut” rule.

Cut down your content and leave only the meaningful messages or images, because people are reading so much content these days that they get lost finding the purpose of it.

C. Collaboration Master

I find it fascinating that even though Kieran left HubSpot he continues to collaborate with HubSpot CMO, Kipp Bodnar.

You rarely hear of someone leaving a company on good terms and maintaining close relationships with former colleagues.

I remember Kieran was only a week in Zapier, and when they recorded a new episode of Marketing Against The Grain, Kipp casually asked him how’s everything going and how’s the unboarding.

Just like a close friend would ask.

Even though Kieran left HubSpot a year ago they still create episodes on Marketing Against The Grain talking about marketing trends, growth tactics and innovation.

They keep up with everything marketing related and try new methods of creating content and growing hacks, and talk a lot about AI.

Once they even did a live podcast episode on the main stage of Inbound.

Kieran said it was incredibly rewarding to share ideas live, to get instant feedback, and build momentum on stage.

Seeing their successful podcast, it’s important to remember that when leaving a company it’s always best to leave on good terms because you never know what the future may hold.

D. Promoter of Zapier

All these CEOs, CMOs, and VPs, have come to realize that to build a successful business you have to promote the business as well.

I’ve seen Dave Gerhardt talking about this since 2019, companies like seeing the importance of growing evangelists like Zoë Hartsfield, and content creators like Obaid Durrani or Todd Clousser seeing the importance of promoting the companies they work for as well.

Kieran, talks about Zapier in his LinkedIn posts and connects his audience with Zapier.

He created a post to announce that they listen to their customers and offered value, flexibility, and more free zaps to create.

That post got 104 interactions. So far I’ve never seen a product post get so many interactions.

If I think about it’s the first time I’m seeing a successful product, reducing their constraints and adapting so well to their customers’ needs.

Kieran also talks about how Zapier employees have integrated AI to help them with their daily tasks and invites everyone to join their event showing how to use Zapier and AI together.

What Zapier is doing with all these listening to customers and helping them use Zapier and AI, has something to do with what they did at HubSpot.

Kieran wrote a LinkedIn post where he mentioned that Christopher O’Donnell, Ex Chief Product Officer at HubSpot, used to say that HubSpot’s job was to help people in their careers, not to sell software.

HubSpot should offer people free tools, educational content, a community to support people and help them be better at what their job is to get promotions.

E. Early adopter of AI

On Marketing Against The Grain, on his X and LinkedIn accounts Kieran talks a lot about AI and how it will change marketing.

He’s not regurgitating content that he reads, he rolls his sleeves and does the dirty job testing the apps out there and seeing how they could be useful.

In one of the recent episodes of their podcast, Kieran and Kipp built a marketing plan with Chat GPT and analyzed what worked and what didn’t.

The platform wrote down the marketing for the next year with details for each month and what people you would need to make your plan successful.

It broke down the campaign to every detail creating OKRs for each employee, thought about partners, and established metrics.

Flanagan said that if he were someone in a company where they were not good at marketing he would have used this prompt.

Kipp completes his ideas saying there is no excuse for marketers today to say they don’t know how to do their work since they can get help from different AI tools.

In a podcast from 8 months ago, Kieran was asked his opinion on AI.

Kieran said AI continuously bundles and unbundles content.

He further explained that people go into AI and give AI a list of bullet points they want to create content around.

After people receive the content, they edit it a bit, and put it on their blogs or social accounts.

Subsequently, AI aggregates this content and returns it to the user, effectively reorganizing it back into bullet points.

This process poses a challenge as creators risk blending in with other summarized ideas online.

He suggests that individuals who excel in their field have typically made significant sacrifices to achieve excellence. 

However, AI provides those with average abilities the opportunity to reach the same level.

The downside is that it becomes increasingly difficult for individuals to distinguish themselves.

Nonetheless, there has never been a smaller window of opportunity for early adopters to extract value before widespread adoption leads to commoditization.

What can B2B creators learn from Kieran?

1. Continue to learn and adapt

Kieran had a background in software engineering and even though he said that working in development was not something he was good at, I think it helped him create a mindset of testing and trying new things.

Kieran’s commitment to staying updated on marketing trends and technologies shows how important it is to constantly learn to remain agile and responsive to changing market dynamics.

So if you want to progress, you too should seek out new tools, methodologies, and insights to stay ahead of the curve and capitalize on emerging opportunities.

2. Learn to focus and prioritize

Kieran realized that being able to focus on the most important things can propel your business.

You should also learn to optimize your time and resources.

Make efforts towards activities that contribute most significantly to your success, minimizing sweating on the things that don’t matter as much.

3. Bring value to your customers

Kieran learned at HubSpot about the importance of offering free tools, educational resources, and community support demonstrates a commitment to supporting customers’ success and empowering them to achieve their goals.

And it’s something he continues to do at Zapier as well, and also on his podcast and social media accounts.

He educates people on using AI, on developing their knowledge on marketing and talks to them about new methods and strategies.

By focusing on value creation, you can differentiate yourself or your business from competitors and build a loyal audience or customer base.

Final Thoughts

Kieran Flanagan is an innovative marketer who has a strategic vision and a forward-thinking approach.

What I like about him is that even though he’s more flexible and easier to adapt to new things, he’s also a data-oriented person, needing to test and to see if a new method or tools actually works and brings value.

Cannot wait to see what he will continue to do at Zapier and how he will continue to develop his personal brand on LinkedIn.

Will he end up creating his own software program? We shall see.