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Inside the Mind of Jake From Retool on Building a Marketing Tech Stack for Product-Led Growth

Akhil G
May 27, 2022

Jake Levinger from Retool is a well-known name in the PLG space with his contributions in the product-led communities, events, and publications. He built the marketing tech stack for Retool - a well known PLG company that helps build internal tools. Jake shared his experience with us in The Product-Led Marketing Show’s very first episode

Having worked in self-service, and ‘request a demo’ funnels at various companies, Jake Levinger brings in a lot of experience in marketing ops and acquired skills as part of his transition from ‘request demo’ to a free trial GTM. 

Key Takeaways 

Experience Transitioning From ‘Request Demo’ to a Free Trial GTM

I asked Jake what was his experience transitioning from ‘request demo’ to a free trial GTM and this is what he said: 

During my time at Carta, if you wanted to buy the tool, you had to go through a sales rep more or less by way of a request demo form or Drift chat on our website. From the marketing ops standpoint, there was a finite amount of things that we had to manage including Marketo, various forms, Drift for live chat and make sure that all these things pipe into Salesforce and then we had to own the email as well. Our go-to-market motion was focused around gated assets and gated content to get people to download stuff, get people to come to events and then send them demo requests, follow ups afterwards, things like that. 

I feel like the GTM motion is the main difference between Carta and Retool. Retool is using product-led growth motion and it has a lower barrier to qualify the leads, but it's still much better than giving someone an ebook with the top 10 ways to build internal apps. Retool’s audience is highly technical and they want us to get out of their way, let them build stuff, let them see if the product is valuable or not, and offer support when they need it. 

However, We still have an enterprise funnel in our business, and we're still trying to define MQLs, and figure out how to get those to the SDRs, how we empower the SDRs to work them and provide value for them, and then suss out who should be an enterprise customer. Also, we have a demo request experience as well. So things aren't that different from Carta. It's just a function of figuring out the best for buyer experience. 

Lessons He Had to Learn or Unlearn When He Switched to Product-Led

I asked Jake about the things that he had to unlearn when he switched to product-led environment and this is what he said: 

There were a few of them, one being able to build a more flexible tech stack and realizing what the foundational components of the tech stack are. 

At a sales-led company, marketing automation systems and the CRM are like the bedrock components. They are usually Marketo or HubSpot and Salesforce. However, in the PLG world, CDPs like Segment are much more foundational than marketing automation systems. When I joined Retool, we didn't have Segment in place, but we had Salesforce, and we had for emailing, which I think was a great tool at that time, but I was thinking that was not a scalable martech stack for the business. 

In a sales-led company, you need an MVP, you need a CRM, you need some sort of a chat tool and enrichment tool, and then some sort of ABM layering on top of it. But they don’t translate one to one to the product-led world. 

So it was like okay, we have Segment and Salesforce, but what should connect between them? Do I need a point to point thing like Do I need to get a more automation type solution like a HubSpot, Pardot or Marketo? Which one of those is best if I decide to go that route? There were a lot of things, being able to kind of rethink the way that data flows and understand what the foundational components are. I think those are things I had to unlearn. 

Retool’s Marketing Tech Stack 

I asked about the tools that he has in Retool’s tech stack for marketing and how they help in product-led growth GTM motion. Here’s what he revealed: 

We have Segment in use, and then Salesforce for CRM. Stripe is a big part of our billing structure for the Cloud customers. Also, we use HubSpot as the marketing automation platform and we use it to trigger all of our onboarding emails. Clearbit is one of the most valuable tools in our stack because its real-time enrichment helps us to reduce the number of form fields and thereby reducing friction.

We also have BigQuery for data warehouse, which is where all the data from other tools gets stored. We use Hightouch for reverse ETL and it’s been a really amazing tool to be able to actualize more value from our more granular product data.

Gaps He Saw While Building a Tech Stack for PLG 

I was curious to know the gaps he saw while building a tech stack for PLG. Here is the answer:  

When I joined Retool, Salesforce, Segment, BigQuery,, and Clearbit were already in place and we had a custom script for creating trial signups in Salesforce. They were working well at that time, but I wanted to build a tech stack that can scale with the GTM motion and business. 

The custom script for creating trial signup records in Salesforce was a weak link in the system as every time we wanted to make any changes, we had to involve the product engineering team and that was a dependency. I knew that over time, that just wouldn’t be scalable and I wanted to eliminate the product engineering dependency for GTM related changes and activities. 

Also, as I mentioned, we were using for emailing, it had incredible integration with Segment, but it didn’t have an integration with Salesforce. We had a lot of contacts in database and Salesforce, but we were unable to scalably pass the data back and forth from Salesforce to So we had to find an alternative for for sending emails and a solution for replacing that custom script for syncing top of the funnel signups from Segment to Salesforce.  

Structuring of Marketing, Sales, BDR, Product, and Customer Success Teams in PLG

I asked him about the changes in the way his teams (marketing, sales, BDR, product, customer success) are structured now. 

SDR team of Carta was under the sales org and they were the recipients of demo requests and Drift chats, and sometimes for the content downloads and events as well. But, there was a very clear distinction between the marketing team and the sales team. At Retool and in the whole PLG industry, that line gets blurrier and the teams work together more closely than at a sales-led company. 

In a sales-led company, when you get a demo request, it goes one of two ways: either they're a good fit, then they go through the funnel, or they're not a good fit, then they kind of get turned away. But It's different for PLG because you can have three options: if someone signs up, and they are a great fit for an enterprise plan, someone signs up, and they're not a great fit for their enterprise plan, but they could be a self-service customer. So there's that third option and we have a self-serve plan for those customers. 

Organizationally, here the SDR function still sits under sales, and they still are quoted on generating enterprise opportunities, just because that's how businesses generate most revenue. But we work with them a lot more closely on figuring out ways to make their conversations more valuable with the people they're talking to on trials, by way of data.

If someone's not a candidate for an enterprise plan, at least they have a great use case for our free tool. So it’s like we set the expectation with the SDR team to get those signups to a successful state. I think here you've got a whole new path that customers can go down to potential customers, which would be that self-serve motion, that’s where the line gets blurrier. 

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