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The Foundational Five: Who They Are and How to Find Them

Insights

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3.11.2025

Dani Johnson and Shilpa Kannan

Having the right team members is critical for any company, but much more so for a startup. There is not much buffer that startups have at the early stages - missing key people or needing to course correct after mis-hires is particularly costly when trying to get your product launched, a customer onboarded, or raising funding. On the other hand, a strong team can rapidly accelerate a company’s progress. At PSL, we see this every day as our incredible team of engineers and designers reduces the time it takes to launch a company from >1 year to a matter of months.

New founders we speak with often have questions on how to go about building their early team - their first 5 hires. Here are a few insights, based on our experience, to the most frequently asked questions.

What are the types of roles you look for in your first 5 hires?

We generally see the “first 5” include: CEO, CTO, 2 AI engineers, and a designer (see questions below about responsibilities). This composition strikes a balance between technical talent (CTO, engineers), sales (CEO), and product (CEO, designer). But the actual first 5 will flex to the type of company. For example, a company building an AI product for marketers may replace an engineer with a marketer.

From a timing perspective, the most important role for a founder to fill is the CTO. The CTO sets the technical vision, so investors will expect to see a CTO on the team before feeling comfortable writing a check. The same goes for hiring additional engineers - most engineers will expect to see a technical vision they can contribute to and execute on before accepting an offer.

How has AI changed how you think about a founding team?

There are two main ways in which AI has shifted the way we think about team building.

First, we have seen design increase in importance. Before the rise of generative AI, there was a relatively straightforward way for how users would interact with tech products. While design was still important, early stage startups could manage by copying design principles of existing companies in the market. But that has all changed with AI. We interact with the latest models and tools in entirely novel ways, and it continually is evolving. Users do not know what to expect from AI products - so much is undefined.

Second, it’s absolutely critical for engineers to have generative AI knowledge and experience, whether through their day job or side projects. The pace of innovation is so fast and unlike anything we have seen for many years - there are new models and technology coming out on nearly a daily basis. You need talent that is able to capitalize on each AI advancement to stay competitive in the market.

What is important to screen for when hiring the early team members?

Across all roles, the most important requirement is scrappiness. People who are scrappy are able to innovate in incredible ways. People who are not resourceful can be a drag on the rest of the team.

CTO

It is mission critical for a CTO to be comfortable coding and have AI experience. The CTO is the first engineer, so they need to be confident they can build the product on their own. We see many people interested in being a CTO that do not realize they have to code - particularly senior leaders from big tech. CTOs need to exemplify this - finding the latest research papers, testing different models, and continually evaluating what is possible.

AI engineers

Engineers need to be tracking new technology and integrate it into their work fast. The types of engineers you need can vary. Having both engineers as full stack can be helpful so that they flex into front end and back end.

Designer

The designer needs to be able to work end to end - going from customer research all the way to the actual UX. They are the CEO’s partner on creating the right customer experience.

What about contracting or outsourcing?

Founders often consider contracting as a means to keep costs down. Contractors inherently are not steeped in your company’s knowledge nor are their learnings kept on as your start-up grows. Eventually your company will need to transition the role from a contractor to a full time employee, which can result in growing pains.

What are common missteps founders can make when building their team?

We often see founders who believe their co-founder needs to be someone they can partner well with for 10+ years. That’s an overwhelming decision framework and an almost impossible one to meet. Companies evolve and people change - you cannot know what your company will look like or what kind of people will be needed in the long term.

What are ways that you leverage AI in your day to day?

Recruiting is a heavily human dependent function today, but our team uses different AI tools to speed up some of the more repeatable tasks. However, we do see a gap in how well tech tools address recruiting challenges and think it is one of the areas ripe for AI disruption.

Of course, there is no perfect recipe for success. Mistakes can and will happen. You might end up with someone on your team who just doesn’t fit, whether culturally or based on skills. But, hopefully by using our and others’ learnings, you are able to build a strong team that accelerates your company’s growth.