SaaS Startups: when to roll out an executive team?

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Learning from a playbook

Learning from a playbook that doesn’t have your active participation as one of the key actors is clearly a borrowed learning. 

Absolutely nothing wrong in doing that, except that you must realize the importance of the context and the playground where such learnings are realized.

But the biggest learning

But the biggest learning I took away from that was that every context is different, every company is different. 

Just because someone has been able to do something successfully somewhere else, it doesn’t mean that they can do it in your context too. 

So, judge people by their actions, judge people by their skills, judge people by the conversations they can have with you, the actual work you see. 

Don’t judge anyone by, you know, titles, or experience, or any of that. That is the biggest learning that I have taken away from hiring for the future.

The timing or the

The timing or the threshold required for onboarding a seasoned executive team is a function of your business, product adoption, and so many of the other signals that define the readiness of your startup in bringing in a chief experience officer (CXO).

Often, founders come and

Often, founders come and ask me what kind of VP of sales should I hire in the US, who will help me?

You should approach it, like, I am just going and starting my company all over again. If you approach it like a market you are trying to hire a sales leader for, it won’t work. 

But you have to say whatever company I built was the wrong company, so let me go start it again kind of stuff. 

You got to go and sit down in the US and understand your customer all over again, do the market fitment, sell. 

You may need some help, you may want to hire a local person, one or two people, but the founding team has to truly approach it like a ‘let’s start a new company’ kind of mindset.

If you are a

If you are a first-time founder in particular or have never run a team to scale, your instincts are often to hire very smart individual contributors. 

You often don’t really understand the leverage of having a great executive in place. That’s why sometimes when you see second-time founders start a company, within their first 15 people, they have three or four VPs and a CXO.

The first three leaders

The first three leaders that we hired in the company— and I was really proud of these hires, like they were marquee hires for us—they came in, and in three months we realized that they were not performing, and that was really hard for us because when you hire leaders, you bring them in, you bring them in a certain way to the team. 

The team starts wanting to look up to them, and then they don’t perform, and then you start questioning yourself and saying, is it me? Is it me, or is it them? Are we doing something wrong? 

We had to let them go, and then we had to rebuild the culture almost from scratch. That was a very hard period for us, in general.

There is one good

There is one good guideline, “If something is not broken, don’t fix it.” 

Thinking that five years later it would be like this or that or maybe two years later it should be like this. If you do not see things break, don’t fix them, especially on the engineering side because India inherently has very good engineering talent. 

I do think we have very solid engineering talent and none of our guys is someone we have got from other companies.

These are all like, you know, straight out of IIT or a good place, so inherently, the talent is very strong, and whenever we have tried to corrupt it by saying “no, no five-year view, people who have run 200-member teams”, it has always flopped. 

It’s probably a culture thing; engineering is a very culture-heavy part of the business.

Often, as a first-time

Often, as a first-time founder, you ask why does this person need all these executives? It’s only a 50-person company! But then, after you have been through a big company and team scaling experience yourself, you realize the enormous leverage you get by building an executive team.

One thing is definitely

One thing is definitely there in our case, and that should apply in other cases as well. 

Dheeraj used to head sales and we both made it our single mission to focus on the US. That means we abandoned everything else. We left it all to somebody else to deal with it, and I will not worry about it. 

So the founders need to become obsessed and personally go drive sales. 

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