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Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916

Kieran Flanagan is SVP Marketing at HubSpot, where he has helped the business grow internationally, move to a product-led business, quadrupled its marketing demand, and built out its media team, including the acquisition of ‘The Hustle.’ He is also an advisor and investor in early-stage companies. ----------------------------------------------- Timestamps: 0:00 Kieran's backstory 1:40 How product-led growth has changed 3:48 What is Growth? 5:02 Who to hire first in Growth? Senior or Junior? 6:47 Is there a role for Growth pre product-market fit? 8:26 How to choose your North Star Metric 9:30 Biggest mistakes founders commonly make 11:10 Growth teams: Decentralized vs. Centralized 13:40 How to structure the hiring process for Growth 17:05 How to do a case-study for a potential Growth hire 19:05 Does the founder need a growth model in place before hiring a Growth leader? 20:10 Biggest mistakes founders make in hiring for Growth 21:32 The signs that an individual can scale with the company 24:07 Kieran's biggest hiring mistakes 26:50 The Future of Content Marketing 29:50 How to make edgy marketing when your company is at scale 32:00 Elon Musk: The Ultimate A/B Testing Machine 33:30 Companies underinvest in content 35:10 Content Distribution 36:40 Attribution of content marketing to revenue generation 38:21 What is "Community"? 39:50 Does Community scale? 44:35 How to market a horizontal product without alienating the verticals? 46:36 What should HubSpot have done differently with regard to Community? 50:27 Cross-functional communication with Growth 53:50 How to onboard for Growth 55:15 Kieran's biggest weakness as a leader 56:00 How has angel investing impacted your mindset? 57:10 Growth Tactics that have/haven't changed over the last 5 years 57:34 Biggest mistake founders make when hiring for Growth 58:09 Advice for Growth Leaders Starting Today 58:27 How onboarding differs for remote workers 59:02 What would you most like to change about Growth? 59:28 How many domains have you bought? 1:00:40 What company's growth strategy have you been most impressed by? ----------------------------------------------- In Today’s Episode with Kieran Flanagan We Discuss: 1.) Entry into Growth and Marketing: How did Kieran make his way into the world of growth and marketing? What has been 1-2 of Kieran’s biggest lessons from seeing firsthand the hyper-scaling of HubSpot? On reflection, how would Kieran summarize both HubSpot’s community building attempts and also their product messaging? 2.) Why You Need Growth Hires Pre Product Market Fit: What does “growth” mean to Kieran? Where do so many get it wrong? Why does Kieran believe that you should have a growth team/people before product market fit? What specifically do they do and work on during this stage? Pre PMF, what is the core metric that all startups should focus on? How does it change with time? 3.) Building Your Growth Team: What does Kieran believe are the 3 key stages to hiring for growth? How should founders determine whether to have external standalone growth teams or integrate them into existing functions? What are the single biggest mistakes founders make when hiring for growth? 4.) The Future is Content: Why does Kieran believe every great tech brand will have to become a media brand? Why is Elon Musk an example of the perfect brand? What has he done right? Why does Kieran say that data is the best and worst thing that has happened to marketing? 5.) WTF Really is Community: How does Kieran define “community”? What is it? What is it not? What makes the best communities? Why do some work and others not? Should every company have a community approach? Who does it make sense for? Have HubSpot done a good job at community building? On reflection, is there anything that Kieran would have done differently? ----------------------------------------------- #KieranFlanagan #HubSpot #20VC #harrystebbings #productmarketfit #growthmarketing #productmarketing #productmanager #communitymanager #brandmarketing

Harry StebbingshostKieran Flanaganguest
Aug 9, 20221h 1mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Kieran Flanagan on Growth Hiring, PLG, Community, and Media Moats

  1. Kieran Flanagan, SVP at HubSpot, unpacks how companies should think about growth across stages, from pre–product-market fit through large-scale PLG, and why the structure and sponsorship of growth teams matter more than labels.
  2. He dives into hiring for growth: when to bring in leaders vs. individual contributors, how to design interview processes and case studies, and common hiring mistakes like over-indexing on personal or company brand.
  3. The conversation expands into brand, media, and community: why tech companies must act like media companies, how to think about unmeasurable long-term bets, and why most “community-led growth” is poorly defined and hard to scale.
  4. Kieran also shares candid lessons from HubSpot’s PLG transition, cross-functional friction between marketing and product, and his views on content distribution, onboarding, and what angel investing has taught him about how hard company building really is.

IDEAS WORTH REMEMBERING

5 ideas

Define growth by its ownership of the full user journey, not by a trendy label.

In PLG companies, growth should own acquisition, onboarding, upgrade/monetization, and retention; in sales/marketing-led businesses it often focuses on performance channels, but clarity on scope and goals is essential.

Instill growth thinking early, but don’t over-build growth before product-market fit.

Pre-PMF, founders should obsess over retention and customer fit, and selectively design product features that inherently acquire and differentiate (e.g., Rap Genius annotations) rather than chasing virality and complex onboarding flows too soon.

Start small with growth hiring, then add leaders when bandwidth and scope justify it.

You can launch growth with a single engineer focused on a core metric; bring in a growth leader once there’s enough ongoing work and cross-functional complexity that the founder can no longer directly manage it.

Use structured, three-part hiring processes and rigorous case studies for growth roles.

Combine an informal fit conversation, formal cross-functional interviews, and a case study where candidates prioritize metrics, design experiments, and defend their opinions—this reveals how they think, focus, and push back under pressure.

Beware hiring based on personal or company brand; dig into actual contribution.

People from elite companies or with big personal brands may have ridden a ‘gravy train’; founders must separate “what you did” from “what the we did,” and not assume visibility equals capability.

WORDS WORTH SAVING

5 quotes

Growth to me is how do I acquire, onboard, upgrade people and then retain them.

— Kieran Flanagan

You should try to grow into the problems you have, not take on other people’s problems.

— Kieran Flanagan

The job of any leader is to make themself redundant.

— Kieran Flanagan

An average marketer at a great company makes more money than a great marketer at an average company because they can ride the gravy train to success.

— Kieran Flanagan

Data has been the best and worst thing to happen to marketing.

— Kieran Flanagan

Defining growth and its role in different go-to-market motions (PLG vs. sales/marketing-led)When and how to build growth teams, including centralized vs. decentralized modelsHiring and interviewing for growth roles, including case-study design and common mistakesPre- vs. post–product-market fit growth, north star metrics, and typical founder errorsBrand, content, and media strategy: inspiration vs. education, and distributionCommunity-led growth: definitions, breadth vs. depth, and Web2 vs. Web3 incentivesCross-functional communication, onboarding, and leadership evolution at scale (HubSpot’s PLG journey)

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