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20VC Prediction Open · timeframe Dec 2027
Flanagan: 95% of B2B buying journeys will start in LLMs by 2027
“Google search is one of the best channels we had in B to B. 80% of all purchases started on Google search. It's predicted by 2027, 95% will start in LLM.”
Kieran Flanagan Jul 11, 2025 ▶ 1:04:14 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
a16z Prediction Not checkable as stated
Flanagan: The AI platform shift favors incumbents over standalone point solutions
“And we've seen like AI may be one of the few platform shifts that actually skews towards the monopolies and conglomerates versus like these individual Companies who just get sucked up and there are features of these existing platforms that get kind of skews to…”
Kieran Flanagan Jul 21, 2023 ▶ 15:34 Growth vs Efficiency: Can You Have Both?
20VC Prediction Not checkable as stated
Flanagan: AI will merge growth and GTM teams into innovation pods
“What I see is AI is starting to collapse all of that into a single function, which is like an AI innovation pod. And the AI innovation pod is trying to figure out How do we deploy AI across like go to market to make it a much more efficient go to market?”
Kieran Flanagan Jul 11, 2025 ▶ 4:26 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Assertion Supported
Flanagan: ChatGPT scrapes 1,500 web pages for every single referral visit
“Six months ago, it was 250 pieces of content scraped, and they give you one visit back. Today, it's 1500 pieces of content scraped, and they give you one visit back.”
Kieran Flanagan Jul 11, 2025 ▶ 26:31 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Prediction Not checkable as stated
Flanagan: Informational content marketing will hold no long-term value due to AI
“Now informational content. I just don't see value in it long-term anymore because people's consumer habits are going to change to just get all of that from AI.”
Kieran Flanagan Jul 11, 2025 ▶ 30:10 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Opinion
Flanagan: EU AI regulations are driving European founders to the US
“And if Europe want to be a hub for excellence and innovation, the rules and regulations we have are forcing founders to still, I think, gravitate towards the US.”
Kieran Flanagan Jul 11, 2025 ▶ 48:23 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Opinion
Flanagan: Traditional management-focused CMOs will become obsolete
“Well, I think the CMO that is really fucked is the one who does people management and moves budget around, right? I think the future is really for super ICs. I think the CMO can actually do the craft. Use AI, ship things, understand how to do things because th…”
Kieran Flanagan Jul 11, 2025 ▶ 56:17 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Opinion
Flanagan: Startups should build growth mechanisms before finding product-market fit
“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 product r…”
Kieran Flanagan Nov 25, 2022 ▶ 16:30 20VC: When to Make Your First Growth Hire? Senior or Junior? How To Onboard Them? How To Monitor Their Progress? from Growth Leaders @ Facebook, Instagram, Lyft, Instacart, Miro and more
20VC Prediction Not checkable as stated
Flanagan: AI will eliminate traditional GTM handovers across sales and support
“I think that is where we're going to go in the future and that you have a singular team looking across the entire go to market, whether that is the self-serve part, the sales led part, the customer success part, the customer support part. Because again, AI is …”
Kieran Flanagan Jul 11, 2025 ▶ 8:27 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Prediction Not checkable as stated
Flanagan: Every corporate function will be smaller in the future
“I think every function is going to be smaller in the future.”
Kieran Flanagan Jul 11, 2025 ▶ 13:29 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Opinion
Flanagan: AI isn't reliable enough yet for autonomous multi-task agents
“I think there are some good use cases for agents, but I do think that in a lot of cases today, AI is still not reliable enough where you can guarantee an autonomous agent can do multitask goal in a reliable way where it will kind of give you the same thing bac…”
Kieran Flanagan Jul 11, 2025 ▶ 15:55 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Insight
Flanagan: AI search optimization requires creating hundreds of micro product pages
“And so actually people could ask questions about your product in hundreds of ways. And actually what you need to do for AI search optimization is have hundreds of, like, micro versions of your product page tailored for all of these different audiences.”
Kieran Flanagan Jul 11, 2025 ▶ 31:24 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Opinion
Flanagan: Memory is an LLM's most defensible feature
“I think it's the most defensible part of an LLM.”
Kieran Flanagan Jul 11, 2025 ▶ 32:58 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Insight
Flanagan: Share of voice matters more than referral traffic in LLM search
“The big change is, and it's a change we have to get comfortable with is, share of voice is a more important metric for LLM optimization than traffic.”
Kieran Flanagan Jul 11, 2025 ▶ 38:23 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Prediction Not checkable as stated
Flanagan: AI will empower generalist 'Super ICs' over narrow specialists
“What I see happening is we're going to go to a place where we're going to have a lot of like super ICs and generalists that are enabled with AI, but can do much, much more.”
Kieran Flanagan Jul 11, 2025 ▶ 51:43 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Prediction Not checkable as stated
Flanagan: LLM referral traffic will reach 3% to 5% in two years
“I honestly think that maybe it's like three to five percent.”
Kieran Flanagan Jul 11, 2025 ▶ 52:36 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
a16z Prediction Not checkable as stated
Flanagan: AI will be a growth tailwind for 12 to 18 months
“There may be like AI is somewhat of a tailwind for like maybe 12 months or 18 months for the best people. And then who knows after that, maybe a headwind across everything.”
Kieran Flanagan Jul 21, 2023 ▶ 3:07 Growth vs Efficiency: Can You Have Both?
a16z Prediction Not checkable as stated
Flanagan: AI natural language interfaces will enable universal product-led growth
“And like AI is a phenomenal unlock for product-led growth because product-led growth will get naturally built into every single product because every single product will have a natural language interface. And so like you will actually be able to onboard the pr…”
Kieran Flanagan Jul 21, 2023 ▶ 14:57 Growth vs Efficiency: Can You Have Both?
a16z Prediction Not checkable as stated
Flanagan: Late-stage marketing will shift from domain specialists to technical generalists
“Marketing, I think might move from like more of a Channel domain expertise to more a generalist. Like we have generalists in early startups. I think that will actually be true of late stage companies because these generalists will be able to stitch together li…”
Kieran Flanagan Jul 21, 2023 ▶ 37:03 Growth vs Efficiency: Can You Have Both?
20VC Insight
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.”
Kieran Flanagan Aug 10, 2022 ▶ 26:01 Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916 · 20VC with Harry Stebbings
20VC Prediction Not checkable as stated
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.”
Kieran Flanagan Aug 10, 2022 ▶ 30:41 Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916 · 20VC with Harry Stebbings
20VC Disclosure
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…”
Kieran Flanagan Aug 10, 2022 ▶ 38:01 Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916 · 20VC with Harry Stebbings
20VC Insight
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…”
Kieran Flanagan Aug 10, 2022 ▶ 49:54 Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916 · 20VC with Harry Stebbings
20VC Prediction Held up
Flanagan: AI agents will be priced against human labor costs
“Yes. I think we're going to price agents against human labor costs, outcomes.”
Kieran Flanagan Jul 11, 2025 ▶ 15:16 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Assertion Partly supported
Flanagan: HubSpot's AI chat agent is booking meetings and closing sales
“We have an AI chat agent that is able to sell now. It's booked in meetings. It's doing sales.”
Kieran Flanagan Jul 11, 2025 ▶ 17:28 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Assertion Not checkable as stated
Flanagan: HubSpot achieved 5x email conversion uplift using AI
“And if you had told me 12 months ago that we could use AI to like five X the conversion rate on email, cause I'm like, ah, look, there's only so much personalization you can do in an email.”
Kieran Flanagan Jul 11, 2025 ▶ 18:26 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Insight
Flanagan: AI enables economical marketing to micro-segments under 300 people
“And the reason we do segment-level marketing is because we need a broad enough group of people to go after to make it economically feasible for us to have a certain size of marketing team to market to you, right? We can't market to, like, Very, very fine. We c…”
Kieran Flanagan Jul 11, 2025 ▶ 20:37 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Assertion Contradicted
Flanagan: AI Overviews now appear in over 35% of Google searches
“That's on over, like, 35% of all searches today have some sort of AI overviews experience, and so that's rolling out much more rapidly.”
Kieran Flanagan Jul 11, 2025 ▶ 26:00 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Assertion Partly supported
Flanagan: Viral AI gorilla ad booked LA dentist for years
“And there's a dental practitioner in the LA who created this kind of looked like a vlog of a gorilla doing a parachute jump, losing his teeth, and then go into his practice to get them fixed. And it went viral. And he apparently booked up his dental practice f…”
Kieran Flanagan Jul 11, 2025 ▶ 37:01 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Assertion Supported
Flanagan: Quora citations in Google AI Overviews have drastically increased
“The real winner of AI search so far is like Quora. Quora is actually, you know, Their number of citations are seen in Google AI overviews has drastically increased because what I said was there's many ways to ask these questions now and AI wants all of that da…”
Kieran Flanagan Jul 11, 2025 ▶ 55:01 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Insight
Flanagan: Growth experiments failing to show metrics in six weeks should be dropped
“If you can't do something in six weeks, it's not worth doing. If you're in growth, right, you actually have to have minimal viable experiment. Figure out if you can do that thing and see a success, what I call an exit metric, but see a success metric after six…”
Kieran Flanagan Jul 11, 2025 ▶ 59:04 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Opinion
Flanagan: Claude's app builder is inferior to Lovable and Replit
“I don't see Claude as being as good as Lovable or Repplet. I think it's much more between Repplet and Lovable”
Kieran Flanagan Jul 11, 2025 ▶ 1:11:17 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
a16z Prediction Not checkable as stated
Flanagan: AI will shift marketing back to unmeasurable, indirect channels
“If you look at where I think things will go with the evolution of AI, people will want to talk to people, so like community becomes much more important, referral becomes much more important, where the mouth becomes much more important. All of these things are …”
Kieran Flanagan Jul 21, 2023 ▶ 3:59 Growth vs Efficiency: Can You Have Both?
a16z Insight
Flanagan: Over-indexing on marketing metrics destroys creativity
“Cause like, cause I think the over index of measurements forces everyone into the middle and everything becomes like mundane and lacks creativity.”
Kieran Flanagan Jul 21, 2023 ▶ 4:21 Growth vs Efficiency: Can You Have Both?
a16z Opinion
Flanagan: HubSpot's media talent from The Hustle is a B2B moat
“And we got incredible talent that I think is a real moat against most B to B companies. Cause they do not have this talent within that company.”
Kieran Flanagan Jul 21, 2023 ▶ 32:24 Growth vs Efficiency: Can You Have Both?
20VC Insight
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…”
Kieran Flanagan Aug 10, 2022 ▶ 5:58 Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916 · 20VC with Harry Stebbings
20VC Insight
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.”
Kieran Flanagan Aug 10, 2022 ▶ 6:57 Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916 · 20VC with Harry Stebbings
20VC Insight
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…”
Kieran Flanagan Aug 10, 2022 ▶ 10:41 Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916 · 20VC with Harry Stebbings
20VC Insight
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…”
Kieran Flanagan Aug 10, 2022 ▶ 12:59 Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916 · 20VC with Harry Stebbings
20VC Prediction Not checkable as stated
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.”
Kieran Flanagan Aug 10, 2022 ▶ 27:56 Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916 · 20VC with Harry Stebbings
20VC Prediction Not checkable as stated
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.”
Kieran Flanagan Aug 10, 2022 ▶ 37:41 Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916 · 20VC with Harry Stebbings
20VC Insight
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.”
Kieran Flanagan Aug 10, 2022 ▶ 42:42 Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916 · 20VC with Harry Stebbings
20VC Insight
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.”
Kieran Flanagan Aug 10, 2022 ▶ 45:18 Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916 · 20VC with Harry Stebbings
20VC Disclosure
Flanagan: HubSpot maintains separate PLG and AI innovation teams
“No, we haven't. Which is why I think I'm going to get in trouble for saying this. So we have a growth team that are very much focused on product led. They do really great work. We have an internal team that is trying to work across AI innovation across like hu…”
Kieran Flanagan Jul 11, 2025 ▶ 6:05 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Insight
Flanagan: Customized AI prompts outperform off-the-shelf GTM software
“What we have found is the more that we customized a prompt for our needs and the way that we customize that for our needs, the results are much, much better.”
Kieran Flanagan Jul 11, 2025 ▶ 10:24 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Disclosure
Flanagan: HubSpot is redeploying support teams affected by AI, not cutting them
“We are redeploying those teams to do other important work.”
Kieran Flanagan Jul 11, 2025 ▶ 13:02 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Insight
Flanagan: Ask AI to write its own prompts for better results
“The number one tip I can just give anyone to get better at prompting is to ask the AI to create the prompt.”
Kieran Flanagan Jul 11, 2025 ▶ 33:52 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
20VC Assertion Not checkable as stated
Flanagan: HubSpot LLM traffic grew 5x but remains under 1%
“We've seen a five X increase, but it's still less than one percent of our traffic.”
Kieran Flanagan Jul 11, 2025 ▶ 38:17 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
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