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Mastering the art of Sales at early-stage startups

Samaipata Editorial Team
May 8, 2024

Written by the Samaipata Editorial Team

This is the third episode of "No-Filter Talks," an interview-based video series that invites our Operating Partners to speak openly about their experiences, offering valuable lessons and sometimes hard-to-swallow truths for our founders’ success.

In the competitive landscape of entrepreneurship, understanding the nuances of enterprise sales is crucial for the survival and growth of early-stage startups. Paulo Rodriguez, Head of International at Vanta, brings a background including pivotal roles as a B2B Sales Director at Dropbox and an Enterprise Sales Engineer at Google. His extensive experience bridges the gap between technical expertise and strategic sales execution.

In this episode, Paulo delves into the essentials of building a resilient sales team, mastering the sales cycle, and debunking common sales misconceptions that can hinder a startup's progress. This interview offers more than just sales techniques; it provides foundational strategies that are critical for anyone looking to thrive in high-stakes sales roles. If you’re an early-stage founder or a professional focused on scaling your enterprise, this is an episode you cannot miss.

Samaipata: What are some common misconceptions in enterprise sales?

Paulo: I think there's a few misconceptions in enterprise sales. The first one that I've encountered is that founders want to outsource sales. Sometimes our technical founders and they feel that sales is not something that they should be doing. I think that's actually a major misconception. I think a founder needs to be able to sell their product. At the end of the day, that's what they do.

I think mostly, especially in tech founders, they feel almost this allergic reaction to sales. Oh, sales is for something else, almost a bit dirty. And me coming from a technical background and having moved into sales, I realise that sales is just a skill. It's, you learn, you pick it up.

And I think it's really important for founders to build those skill sets in sales. When you bring in a salesperson that may not have that level of curiosity that you have, then you're actually selling yourself short and doing your company a disservice because you're failing to incorporate customer feedback to that process.

The other common misconception I find quite often is that everybody's looking for what's the right way of doing it. Well, the right way of doing it doesn't exist, right? It really depends on what stage are you as a company, what resources you have available to you, and how you want to sell your product, right?

Some companies may want to go into the enterprise space, and that is a completely different sales model than you trying to sell almost in a B2C environment, which is usually when you sell to SMBs, where you probably are going to a more automated product like growth motion and self-service versus the other one that is super people intensive. You need to have a team of sellers, not just a seller.

So there's no right one size fits all. You need to look at your business, you need to look at your target market once you have a good understanding of how you wanna sell your product and to which audience and you need to start building the right team. And by the way, that team will not be there forever. It will have to change and evolve and probably every couple of years you will have to change the way that you sell. And that is perfectly okay and it's perfectly normal.

Samaipata: What’s the secret sauce for scaling Sales in startups?

Paulo: When you start seeing certain indicators, you can start scaling your sales team. The first one that I would highlight is that you have a repeatability of your sales cycle. Like your sales cycle starts becoming, oh, I know what's gonna happen next and now I know what's gonna happen next. And you keep doing it again and again, and you start seeing patterns. I think that's actually a really good thing that you're starting to figure out.

What's your sales playbook? Probably the thing that you need slightly before that is to find a really good market niche for you to sell it for some companies. I'm gonna sell this product to startup founders in FinTech. For some of them, it's gonna be, I'm gonna sell it for SMBs that are scaling. I'm gonna sell it to enterprise customers that have challenges with A, B, and C, right?

And it could be as niche as I'm gonna sell it to companies that just hired a CFO that wants to make an impression in their new company. And when you start finding those patterns, then you can start combining your reputability of your playbook and a very good target audience, and then you can start exploiting that and then you start scaling it and start moving to adjacent areas of the market.

But I think once that is one of those things that I'm like, cool, you got that secret sauce. You now know how to do this, how to iterate it, go for it.

Samaipata: How would you structure a Sales team from scratch?

Paulo: So I think the way I would structure a sales team is, first of all, founders need to be the one selling. You as a founder need to learn those sales skills and then start selling. And once you start finding repeatability in that sales process, I think that's the moment that you need to start adding more people into that sales team.

Start hiring salespeople that have a very strong entrepreneurial mindset, right? Similar to you as a founder. People that are curious may not have the sales credentials of somebody that has sold enterprise deals at a large software company, but those people are curious and are gonna help you find a better product. Market fit is gonna help you find areas in the market where you can penetrate easily.

Whereas if you go and hire people that are just good structured salespeople, you will need to give them a playbook and they will follow it to the T. But you need to build that playbook first. Go and figure out how to build a playbook. Then you can start scaling your sales team.

Samaipata: How can founders balance immediate Sales results with long-term growth?

Paulo: Every founder is gonna find themselves in the situation of:  “Okay, I need to show that I'm getting somewhere, but also I want the best long-term results for my company”. And sometimes it feels that those are incompatible.

I think the key is being very honest with yourself on what you're trying to achieve, who you're trying to sell to, and setting the right expectations across the board to yourself, to your investors. So everybody understands what's the time horizon for you to get those results.

If you're selling to enterprise customers and that's actually what you wanna do, you cannot honestly expect a turnaround of three months. It's not gonna happen. Yes, you may get lucky sometimes, but really you're looking at a six to nine month sales cycle. You may not have product market fit. Actually, no. We may have product market fit, but the sales cycle is extremely long.

What I normally recommend people to do is to try to find leading indicators. If we were to sell to a company in the next 12 months, what needs to be true in month three, six, and nine, right? And start measuring those things that you can say, uh, it looks like if we end up selling, we're already ticking all these boxes.

Samaipata: What would be your 3 top pieces of advice for a startup founder willing to master the art of Sales?

Paulo: I think the top three things I would advise a startup founder to do is, first of all, go and sell it yourself. You are the expert in the topic. Even though it may feel irrelevant or painful, it's actually worth every penny.

The second thing I would recommend a founder to do is to find a market segment, uh, with a certain degree of repeatability. When you're in front of that particular customer that is either an industry or a role that you're selling to or a particular company size, or whatever persona your product team has defined, that you're able to sell effectively to those people.

When you start seeing that, then you know that you have an effective playbook. And then the third thing I would, I would recommend people to do is whenever you start spotting those trends, it's like, cool, it's repeatable. You can do it more, and we know exactly who to sell to and it's successful.

Then start scaling your sales team. That's when you're ready to go and hire salespeople. You have a playbook ready for them. You have a set of resources ready for them. You can guide them into that sales process, and you can actually scale really effectively how you sell to those customers.

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