Hiring the proverbial “first VP of sales”

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There are a few

There are a few different signs, but part of it is also the degree to which you have done customer development before you have shipped the product. 

Some companies hire a VP of sales really early, simply because they feel they have proven that the market exists. 

They may hire a VP of sales a few weeks before a launch so that as you actually launch an enterprise or SaaS product, you have somebody who’s really driving the go-to- market (GTM) motion. 

We were very late

We were very late on that. By the time we got sales leaders or salespeople into the company, we had some 40–50 customers. 

And that time, it was very painful to grow and also hire a team and also ramp them up. So we were definitely quite late on the sales hiring side. 

Similarly, on engineering and stuff, I wish I had not hired a VP of engineering.

Often that happens in

Often that happens in cases, for example, where you have built an adjacent product before, and you know there is a real need, or where you build the same thing internally over and over for internal customers, and then you are now selling something externally. 

PagerDuty was a good example of a company where every engineering team eventually built a PagerDuty-like tool, and then they just built it for everybody. 

So, there are some moments where it is kind of clear that what you have is going to be needed, and you want to hire somebody even before launch.

I feel it’s better

I feel it’s better to hire a consulting firm. There are some decent quality sales consulting firms that can help you understand how you are pitching, what you are doing and help you refine that for the market. They are more useful than hiring a VP of sales, I feel.

In fact, the first two people I hired in sales never worked out. I thought they were from the industry, and it would work out, but it was totally useless.

We hired our first

We hired our first VP of sales at $2 million in revenues to help build a sales org and to make the shift from founder-driven sales to GTM org-driven sales.

Once you have got

Once you have got your, I would say, first five to ten customers on the enterprise side, and you have a repeatable playbook, that’s the right time to go and hire because what a VP of sales can’t do for you is create that initial playbook which a customer wants to buy from you. 

But what I have seen good sales leaders do is that once you have a playbook, they sell that to more people, that they do well. 

I would not put it as time; I would put it as once you have got ten meaningful customers who are sticky and happy and you know exactly how to sell to the 11th or 12th guy, that’s the time to go and get a good sales leader.

Key TakeawaysHiring for the

Key Takeaways

• Hiring for the future and managing the present.
• Read the signals for getting the timing right.
• Founder CXOs wear multiple hats.

One mistake we made

One mistake we made was to underestimate the importance of go-to-market. 

When I say go-to- market, I mean hiring salespeople, building customer success and account management, and even simple things like actually investing in paid advertising. 

Both Sparsh and I being engineers, there are pros and cons to everything. The problem was that we were engineers, so we were just very knee-deep into building great products, and we thought that a great product would do everything by itself. 

The company will grow

The company will grow behind its back and we don’t know why we need sales, why we need marketing, and so on. 

But, over time, we realized that we are in the business of delivering value to humans, and the product is one way of delivering that value, but humans like to get on a phone call sometimes and talk to people and interfaces and screens can only go that far into doing that. 

Very reluctantly, we hired our first salesperson, and that is when we realized, wow! There is a ton of value we can create if we focus there!

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