Topic
Go-to-Market
GTM strategies from PLG to enterprise sales.
What the experts say
“The best approach to reading sales and GTM books is to extract two or three valuable ideas from them rather than follow them as complete playbooks.”
Lenny's Podcast · 1:29:56
“Many go-to-market and sales books function as rigid playbooks that become outdated, particularly those selling courses, rather than as collections of flexible plays.”
Lenny's Podcast · 1:29:56
“GTM playbooks are not working as well as they used to because the current business landscape, particularly regarding AI, has changed significantly.”
Lenny's Podcast · 1:29:56
“Vercel's addition of Janine indicates they are moving toward enterprise sales.”
Lenny's Podcast · 1:17:14
“The bar for what constitutes 'good enough' AI-powered go-to-market is lower than many people think—it only needs to replicate your best performer well enough to outperform your mid-pack and underperforming salespeople.”
Lenny's Podcast · 46:24
“Ruthless efficiency will be the primary focus for companies in 2026, particularly where AI can be effectively deployed.”
Lenny's Podcast · 15:21
“Datarails used a spreadsheet-based approach to organize territory metrics and company size data to systematically divide the LinkedIn market for outbound prospecting.”
The PMF Show · 31:29
“The founders built a powerful outbound motion as a core go-to-market strategy rather than relying on third-party lead sources.”
The PMF Show · 30:37
“The main challenges in reaching mid-market customers are high customer acquisition costs and capturing their attention.”
The PMF Show · 33:45
“We don't start marketing before we have organic growth, and we don't begin building proper product features without evidence of organic growth first.”
Riding Unicorns · 30:38
“The optimal launch strategy is to deploy a global product everywhere first, then identify markets and user groups showing organic growth and traction before investing marketing and product development efforts.”
Riding Unicorns · 29:53
“Operating across multiple countries enables economies of scale that allow companies to go to market and attract customers at a lower cost than single or two-country operators could achieve.”
Riding Unicorns · 29:14
“Founders should prioritize figuring out distribution and go-to-market strategy before or alongside product development, not after.”
Riding Unicorns · 3:35
“Founders and early-stage startups often have little to no idea how they will distribute their product to market, or have only vague ideas rather than well-thought-out strategies.”
Riding Unicorns · 4:23
“WorkOS serves as the fastest path to becoming enterprise ready, whether you're a seed stage company landing your first enterprise customer or already large and expanding globally.”
Acquired · 1:08:14
Related episodes
go-to-market strategy
Distribution
distribution
do you choose the verticals that are the biggest in the PLG side of the business and go after them. And so what I mean by that is you look at Notion or Slack and you go, okay, financial services is a big component of our PLG users that also has...
between customers? We often hear about a sales playbook, which makes us think that you could bluntly press play, and it's kind of the same passer in terms of, hey, well, here's our solution, and these are all the problems it solves. How uniform are...
And so if I think back to all of those founders, they eventually come around and realize that building sales is going to be vital to continue accelerating your company forward. You shouldn't try and reinvent the wheel when it comes to sales. And so...
When founders come to me and they say, I want to go after Walmart, Nike, you know, insert large enterprise logo, I will, 10 out of 10 times, push back and say no. And I know enterprises are tempting. Big logos, big ACVs, they look great on investor...
If your money collection is gonna happen through sales team primarily, then you absolutely should be hiring sales way before growth. In fact, in the sales led companies, growth teams are not necessarily needed, even that much. You might have a...
There were student groups that were using Slack to work on projects. And the sales team was tempted to sell them because our sales team was using product led growth signals and seeing what are the biggest workspaces because lots of active members...
but they become like a stand alone and independent beast. Where do they sit? I don't think it's about the perfect place, as at the end, it's about people, company's DNA, product and marketing leaders' skill set, and you cannot bucket people into...
What do you mean a C suite that gets it? And what does investing in PLG actually look like in reality? Absolutely. So the core idea is you can invest in bits or atoms. Bits is in the product. Atoms is in distribution or sales. Like a person that...
So it comes to the way how we basically launch products and how we run the whole play. The way we operate, first, we're gonna UXR the area and see, like, if there is something there worth our attention. Then we're gonna do some fake door door tests....
So we basically shut everything down, reallocated investments to really go after them, and earned the right for them to use the product again. And that's where the whole machine was built on. Divest everything else, invest where we are default. So...
Not every product can drive word-of-mouth loop, but they can drive recommendations, and they can create user generated content. One of those tactics usually applies to at least one product. So there is an opportunity to create some sort of earned...
Unless you're starting to do self serve revenue, so you're trying to have product sell itself, through potentially freemium acquisition, trial acquisition, or you actually having product led activation, monetization, that's when you would need a...
message flagging within a community. Those groups also don't have a lot of money. And so while they might have had a lot of licenses, there's not a lot of budget to unlock there. And so we made a very deliberate decision to not focus on communities....
Sure, a large marquee logo is expressing interest, engage with them, but don't count on them as your answer to hitting your target. You wanna still be prospecting into good fit companies who have a reasonable sales cycle which will help you build a...
in one quarter you build and optimize for x, in another quarter you need to rewrite the whole thing and like rebuild what you have built because it doesn't stick anymore. This is the mindset. You need to be ready and open for the changes all the...
enterprise. But what we did find was the needs of the the customers that wanted to go through the sales process and required a consultative sales sales process, they typically had let's think about, like, what are some of the reasons why they wanted...
Most of growth loops spin out, their ability to produce meaningful results for you within the first five to six to seven years. So continuously overlaying those different growth models. And what I'm specifically talking about is product led growth,...
I totally get you. No. I I agree. I am brilliant, actually, at sales. So yeah. I know. I was gonna say here, you are brilliant. The fact that on the fifty third email, you got Marc Benioff to come on your show is so impressive because that's the...
Yeah. It's adapt or kill. So we went through this at HubSpot. You know, the first product we built, it's now called referred to as the sales hub. But at the time, it was essentially a bottoms up tool for sales folks that let them track their emails...
apple, whoever owns all these huge distribution platforms, they do not give an F about your product. They are the ones determining the rules of the game. And so your product has to play to those rules, right? That has to mold to those rules. Right?...
Have a podcast?
Run your podcast through Clypt
Get ranked clips, hooks, and ready-to-post copy from your own episodes. Free to try.