Aug 10, 2022 · 1h 1m · news
Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, host Harry Stebbings interviews Kieran Flanagan, Senior VP of Marketing at HubSpot, to explore the tactical mechanics of product-led growth (PLG), recruitment strategies, and the transition of software companies into modern media brands.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 21.7% of the talking time here. How this is scored →
Harry as informed peer 3.8 Guest teaching 5.9 Guest disagreement 2.0 Harry pushing back 3.2
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 6:29 Defending Pre-PMF Growth Mechanics
Kieran rejects Harry's premise that growth functions only exist post-PMF, using Rap Genius's lyric annotation features to show how viral acquisition mechanics can be built directly into pre-PMF product roadmaps.
Hardest push from Harry ▶ 28:34 Challenging HubSpot's Bland PositioningHarry refuses to accept generic marketing generalities and directly challenges Kieran on whether HubSpot itself has become a bland corporate brand sitting safely in the middle.
Biggest teaching moment ▶ 46:45 Community of Product vs Community of PracticeKieran provides a masterclass distinction between a product-focused community and a community of practice, candidly pointing out how even HubSpot failed to link educational achievement with peer-to-peer practice networks.
Harry holds his own ▶ 6:29 Citing Seven Growth Experts Against Pre-PMF GrowthHarry pushes back firmly against Kieran's suggestion of pre-PMF growth by citing consensus data from seven previous growth expert guests who all contradicted Kieran's stance.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| The Evolution of Product-Led Growth | 2 | 5 | 1 | 1 | Harry asks a foundational opening question about how PLG GTM strategy has evolved. Kieran outlines a three-stage evolution model (chaos, centralized, decentralized) and highlights how Reforge standardized growth frameworks. | |
| Defining Growth and Early Team Structuring | 3 | 6 | 2 | 3 | Harry interrupts his own question flow to demand a strict definition of growth before proceeding. Kieran delineates growth across PLG versus sales-led models and advises on hiring single engineers versus growth leaders based on bandwidth. | |
| The Role of Growth Pre-Product Market Fit | 4 | 7 | 3 | 5 | Harry challenges Kieran by citing seven previous growth guest interviews where all stated growth only exists post-PMF. Kieran pushes back with the Rap Genius annotation example to demonstrate pre-PMF growth mechanics built into product roadmaps. | |
| Centralized vs. Decentralized Growth Organizational Structures | 2 | 6 | 1 | 1 | Harry asks how founders should structure growth teams between isolated central units or integrated product teams. Kieran breaks down org design frameworks across consumer marketplaces like Airbnb, product-led SaaS like Calendly, and sales-led orgs. | |
| Designing a Bulletproof Interview Process for Growth Hires | 2 | 5 | 1 | 2 | Harry inquires about structuring an interview pipeline from scratch. Kieran details a three-part framework (informal, formal, case study) and cites the beginner's mindset concept to advocate hiring for growth stretch over pure past repetition. | |
| Crafting and Evaluating the Growth Case Study | 1 | 6 | 2 | 2 | Harry candidly admits he wouldn't know what to give candidates in a growth case study. Kieran explains how to structure a theoretical growth model and intentionally test candidate conviction by challenging their proposed experiments. | |
| Leadership Scaling, Making Yourself Redundant, and Hiring Traps | 5 | 5 | 2 | 2 | Harry uses background intel from Kieran's colleague Kip to ask about leadership scaling and hiring mistakes. Harry contributes strong commentary on the trap of hiring candidates who rode gravy trains at big tech companies like Google or Facebook. | |
| The Death of Bland Product Messaging and the Rise of Brand Point of View | 6 | 6 | 3 | 6 | Harry passionately attacks bland product marketing and explicitly asks Kieran if HubSpot is sitting safely in the middle. Kieran acknowledges the lifecycle of disruptive messaging, explaining how winning a conversation turns transformational messaging into standard best practice. | |
| Creator Networks, Content Distribution, and the Data Dilemma | 5 | 6 | 2 | 3 | Harry highlights how most companies fail at content distribution and questions strict revenue attribution. Kieran details the logic behind the Hustle acquisition and explains how over-reliance on short-term data metrics neuters creative brand building. | |
| Demystifying Community-Led Growth | 6 | 6 | 3 | 6 | Harry aggressively demystifies community as a meaningless buzzword and challenges its ability to scale, citing Y Combinator's quality dilution as an example. Kieran agrees and provides a framework on balancing depth versus breadth across Web2 and Web3 models. | |
| HubSpot's Community Lessons and the Challenge of Intangible Budgets | 5 | 7 | 2 | 4 | Harry asks Kieran to evaluate HubSpot's community efforts self-critically. Kieran provides an honest breakdown of how HubSpot succeeded at building a product community through Academy but missed creating a true community of practice. | |
| Cross-Functional Comms, Onboarding, and Leadership Vulnerability | 4 | 6 | 2 | 3 | Harry probes Kieran on cross-functional communication friction, onboarding standards, and personal leadership vulnerabilities. Kieran shares lessons on moving away from black-and-white thinking and admitting operational admin as his primary weakness. |
Statements from this episode (26)
Growth functions will decentralize into product management roles
“I think at some point you can see growth being much more decentralized into just how PMs create the product itself. We build in mechanisms to promote the product through virality or these other things. We build onboarding flows. We build upgrade flows to get p…”
Growth teams in sales-led companies rarely touch the product
“If you're in a marketing or sales-led business, you do have growth teams, but they predominantly look after performance marketing channels like search paid, paid advertising, affiliate. Like they don't touch the product because it's a marketing sales-led busin…”
Startups can build an initial growth function with a single engineer
“I think you can start with engine. Like I, I've talked to great companies who have started growth with a single engineer. If you really define a core. Metric that you want that engineer to move.”
Growth tactics and experimentation apply even before product-market fit
“I think growth could be applicable pre-product market fit, right? When you actually are trying to figure out how do I instill these mechanisms within my product to better acquire people, to better onboard people, to better retain people, it's built into your p…”
Dedicated growth functions should only be established at Series A
“Proper growth function is series A and beyond, right? And that's like typically the advice you would give, like series A beyond, you have users, you have things that you want to start to actually grow.”
Startups should target retention pre-PMF and revenue post-PMF
“Pre-product market fit is retention. You're looking for a cohort of users that, you know, will use your product in a meaningful way and post-product market fit, it's revenue.”
Building growth loops before product-market fit wastes resources
“A lot of the times I've talked to founders in pre-product market fit, they're obsessed over things that just are not that important right now. They don't need to worry about how do I build great onboarding flows. They don't need to worry about how do I build v…”
HubSpot underestimated the organizational changes required for product-led growth
“We really underestimated the change in team structure going from a traditional SaaS BDB company to like a PLG company”
Growth teams in sales-led SaaS are just rebranded performance marketing
“In a marketing and sales led business where you have a demo trial, you really have the growth teams you find in those businesses sit on marketing and they just run performance marketing. So in the heyday, they were called performance marketing, but growth soun…”
Growth case studies should test metric prioritization and experiment design
“In growth, you can build a great case study because you can give someone a theoretical growth model. You can ask them to tell you what metric they would prioritize, how they would run a great experimentation process, give you three different examples of experi…”
Interviewers should intentionally challenge growth candidates' case study proposals
“Within the questioning, what I would do is I would actually counter and say, I think one of these experiments is much, much better. And these are the reasons to see if they actually have a strong point of view, to see if they're not scared to actually say, hey…”
Give growth candidates pre-built models to test difficult trade-offs
“The reason I like to give them the data beforehand, and the reason I tell founders that it's cool to give them the model beforehand, because if they were just picking, doing the model themselves, that they can't really challenge themselves. It's kind of like b…”
HubSpot's internal media organization has grown to approximately 80 people
“I built at the kind of like media org within HubSpot. It's about 80 people now. We acquired the hustle, and so I kind of put all of that together”
Average marketers at great companies earn more than great ones elsewhere
“An average marketer at a great company makes more money than a great marketer at an average company, right? Because they can ride the gravy train to success.”
Companies should hire meme creators to improve product messaging
“If you want someone who gets product messaging, Hire people who specialize in memes and gifs, because they know what resonates.”
Brands with neutral, uninspired product positioning will struggle
“Brands who don't get with that and don't know how to plug into the culture of today and sit in the middle saying boring things and being boring in terms of their product position and brand, I think they will They're going to struggle.”
Every technology brand will eventually become a media brand
“To me, the whole, every tech brand in the future becomes a media brand because we have something to say.”
Only 5% of founders can pitch their company in under ten words
“I'd say five percent can articulate what their company does in 10 words or less and tell a story with it.”
Creativity and brand will build the next generation of mega-companies
“I think creativity and brand is how you build a big company in the future.”
HubSpot acquired The Hustle based on brand vision, not metrics
“We did the hustle deal. We did not do the hustle deal based upon metrics, right? We did not pitch the board and say, oh, these are all the kind of cool metrics. It's a bet on how we want to be seen within the future, how we want to build our audience in the fu…”
Communities degrade as they scale, as seen with Y Combinator
“With scale, you have community denigration. We see this with Y Combinator, for example.”
Community-led growth yields few winners, but they capture exponential returns
“I think the number of winners in community led group is small, but they get exponential returns because how many community communities can someone be part of two, three. So a small amount of winners, but they get exponential returns.”
Horizontal software tools stay broad for distribution and verticalize to monetize
“I think most of the horizontal tools, they stay horizontal to get mass distribution and they verticalize to monetize.”
Tying all marketing initiatives to immediate revenue prevents differentiation
“If we tie everything to revenue, then we're all going to do the same stuff. Like, we really are going to do the same stuff for the most part. It's not going to differentiate that much, and it's hard to build something differentiated when we're all measuring ou…”
Product managers define problems while marketers focus on solutions
“The job of a PM, great PMs crystallize problems and then present them to their engineers and their engineers are like, oh yeah, we believe in this problem. Here's how we think about this problem. And we will go and figure out how we build that solution, right?…”
Canva scaled search traffic by templatizing features and creating a marketplace
“So what Canva did was they templatize their entire, like everything you can possibly do with a product to create a template for, then they actually created a marketplace. So now people can actually create their own templates. And you can buy them, which extend…”
Shorts cut from this episode
▶ Web2 vs. Web3 ⚔️ #shorts · 20VC with Harry Stebbings (@42:24)
▶ The Three Pillars of Community #shorts · 20VC with Harry Ste (@43:23)
▶ Data is the BEST & WORST thing to happen to Marketing - Part (@37:41)
▶ The future of CONTENT MARKETING · 20VC with Harry Stebbings (@30:48)
▶ Data is the BEST & WORST thing to happen to Marketing - Part (@36:56)
▶ HubSpot VP Analyzes Elon Musk's Marketing Strategy #shorts · (@32:11)
▶ What is Community - Part 2/2 · 20VC with Harry Stebbings (@39:09)
▶ What is Community - Part 1/2 · 20VC with Harry Stebbings (@38:33)