Growing up, I was a nerd — a mathelete to be precise. I idolized the great scientists and mathematicians, not so much the great statesmen or politicians. That's why I found myself in tech and Silicon Valley — a place where us matheletes can make and bring to life what we imagine. And, what better place to make things than a startup, where ostensibly we are unfettered in our technical pursuits.

I’ve had the luck to be a startup CEO twice, and it’s the hardest job I’ve ever had. I currently run Aryn, and a dozen years ago, I ran Amiato, a big data startup. A CEO’s primary responsibility is to sell. I sell a vision of technology and the future to employees and investors. More importantly, I am chief salesperson, so I must convince customers to buy and use our product. While the former comes naturally, the latter has been and continues to be a tremendous learning experience.

I confess that I have imposter syndrome. To cope, I've developed three maxims over the years to help  guide a nerd like me in an approach to sales:

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1. All transactions involving money are enabled or gated by human emotion.

Whether you're purchasing groceries in a supermarket or closing a deal to buy a supermarket chain, emotions play a critical role. Shoppers think twice about a sad looking apple, even though looks are not an indication of taste. Similarly, large acquisitions are notorious for falling apart or escalating because of fear or — the fear of missing out — on the part of decision makers. Even when transactions are automated, e.g. monthly utility bills or algorithmic trading, someone must trust that the automation will work as expected.

Conversely, creating a "wow" moment for a customer makes it much easier to sell a product. My previous startup, Amiato, was an ETL service that loaded data warehouses in the early days of the cloud. We landed our first and largest customer, a mobile gaming company, by automatically loading large and messy online game logs into Amazon Redshift in less than 15 minutes. The lead PM for the game immediately began working with those logs in Excel, and it saved the game’s launch and helped fuel its growth. At Aryn, we've created a similar "wow" experience for loading and analyzing complex business documents.

As a founder, when you see a customer experience the "wow", you know you've got something.

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2. One company's dysfunction is another company's opportunity.

All companies are dysfunctional, some more than others. That's because as organizations grow, it's hard to align the priorities of individuals and groups across the organization. As a corollary, the larger the company, the more dysfunctional it tends to be. Dysfunctional companies are often hard to work with as customers, but my advice is that if you can figure them out, the opportunity is worthwhile.

For example, Amiato’s mobile gaming customer had a central IT team whose responsibility was to make activity logs accessible to PMs for all their games. But, they only had the bandwidth to serve the most lucrative properties. And, the process was onerous, requiring multiple rounds of schema and table design, decision making meetings, and updates to the game to meet the design. No one had time for that in a fast growing mobile business.

We came in and cut through all of that with our automation, relieving pressure on the central IT team and delighting their customers. So, they eventually adopted it for even more games. Similarly with Aryn, we’re expanding in our large enterprise customers as satisfied users tell others.

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3. In enterprises, people are not only buying the product, but also buying a partner for a journey.

Enterprise problems are complex. So, while a product may solve an immediate need, buyers are often looking beyond that to see how to solve adjacent or future needs. These customers are also on their own journey with a mission to fulfill. To de-risk their outcomes, these customers tend to buy from the hyperscalars, because hyperscalars have the widest variety of options and are likely to be around for the entire journey.

But, the hyperscalars’ strength — their breadth and scale — is also their weakness. They cannot pay equal attention to every customer and their complex needs.

As a startup, the only way to win against them is to give enterprise customers something that hyperscalars cannot — your full undivided attention and support. You need to be hyper obsessed with the customer's specific problem and stand shoulder to shoulder with them on their journey. You need to help them navigate their complex needs, filling the gaps that they cannot. You need to feel the sways and bumps in their journey and protect against those that you can anticipate. This will build trust, especially with the best customers that can propel a startup.

Our customers at Aryn are exactly these large, complex customers who want to navigate and benefit from the fast moving generative AI landscape. They want to work with us because they   cannot keep up with the smorgasbord of options and fast pace of changes. The hyperscalars provide infrastructure, but they don't help them solve their specific business problems. While generative AI seems magical, it's not easy to match the technology — whether its analyzing text, tables, diagrams, and images — to the business problem they have — discovering precedent from legal filings, reducing fraud in KYC onboarding, or winning RFP bids for technical projects.

That's where we come in and help them go end to end. While we're doing things that don't scale (as all early stage startups should), we are learning a ton and having fun along the way. We are winning the trust of large customers one by one. The lessons from each compound in not only the product but also the sales process, and build up to an avalanche of growth.

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Conclusion

My friends who went to business school tell me that I am confused. That I don't know what I'm saying when I talk about "go-to-market". They tell me about various sales "playbooks", and so on. I must confess those are terms that come naturally to athletes, not matheletes. So, I've developed the maxims above and live by them to guide and prioritize what I do in selling to customers. And while I have not studied the great industrialists in the art of sales, being humble, and deeply understanding and respecting your customer goes a long way.