Crayon’s office

Walk into the spacious, open offices of Crayon in Boston and you might never have believed that this was Jonah Lopin’s second startup, but his foray into entrepreneurship actually started at Hubspot. MBA in hand, he had wanted to exit the corporate bureaucracy and work with a small, passionate team to build a brand new product category. Little did he know that this experience would provide the backdrop for his next major venture.

Jonah’s path to entrepreneur wasn’t linear. He started out as a management consultant at Deloitte, but ended up wanting to learn more about startups. One MBA program later, he was hooked.

At MIT Sloan, he met his future co-founder, John Osborne, and discovered the hidden world of starting companies from scratch. No bureaucracy. No politics. Unlimited upside with the right idea. Break the rules without worrying about bosses. What’s more, the premise behind startups matched his values. As a kid, he had been homeschooled and learned to think for himself, operate outside of the conventional school system, and believe in constant improvement.

As graduation approached, Jonah skipped the wave of corporate recruiting in favor of an, at the time, risky proposition: joining Hubspot. Entering as the sixth employee, he got onto the management team to run the customer success division. While working with clients, he identified several issues that would later be addressed by Crayon. 

Customers generated a massive amount of leads through Hubspot’s inbound marketing, but they didn’t get the insights to close a competitive sale. Hubspot improved website optimization, but it didn’t help clients with positioning. The team helped people generate content, but they couldn’t help them keep up with what buyers needed in the rapidly changing economy. These challenges were universal. As Jonah put it, “we never helped our customers understand what was happening outside the four walls of their business.”

Working in the Customer Success division, he also picked up valuable soft skills. While dealing with clients and the variety of problems that popped up on a day-to-day basis, Jonah realized the significance of the revenue hockey stick and getting cash flow. Having enough money meant he could run experiments, solve problems, make investments, and attract world class employees. He also had to build a great team; Jonah assembled a cadre of visionaries, problem solvers, and leaders that were “the best people [he’s] ever worked with.”

When Hubspot went public in 2014, Jonah was ready for a fresh start and left to start a company with his MBA classmate John. He had went through a controversial career choice before when he took half the salary of a cushy consulting job to join Hubspot, but it had worked out perfectly. And this time, with a treasure trove of knowledge about marketing and client problems, a playbook to deal with issues at startups, and a roadmap to growth that he had witnessed at Hubspot from zero to IPO, he was more prepared than ever.

He quit his job, assembled a team, and began experimenting. Jonah and John launched a number of products from a location based social network to a GIF style consumer product and even a meal share/meal delivery service before they settled on Crayon Inspire, a Pinterest for marketing.

Part of the Crayon Team

In the first year of building and scaling the product, they realized they weren’t making money, and worries about generating revenue were creeping up. Luckily, the chance to pivot was right beneath their noses. The Crayon Inspire software was crawling the web at scale, indexing and tracking millions of web pages and data sources across millions of companies, organizing and storing that data.

That mass of outside data could be used to solve the problem Jonah witnessed back at Hubspot: the lack of knowledge about metrics outside the four walls of a business. Sensing an unmet opportunity, Jonah and John figured that they could use the backbone of the Crayon Inspire software to run a new service to collect massive amounts of data about companies in a competitive set and generate insights to use from days to years.

They approached two CMOs with the idea and suggested that Crayon could solve their companies’ marketing intelligence problems. Without having even built a product yet, the two potential customers turned into clients and they closed their first sale. It was convincing enough to the two of them that they were on the right track.

When they had come down from the high of the first sale, Jonah and John knew that they had a unique, unheard of idea in a net new category. 

To sell it, they focused on telling a compelling story. 

The narrative started with an analysis of the current situation. Businesses were great at understanding what was going on internally: they had CRM, analytics, real time software data, and optimization strategies for their campaigns. But outside of that, there wasn’t a good way to get information on the wild west of their respective industries.

Potential clients loved the ability to wrap their arms around all these data and signals to generate actionable, software-driven market intelligence. They could get ten times better intel at a tenth of the cost.

It also helped that they made it accessible (you could try it for free) and they took a lot of the strategies that Jonah learned at Hubspot like inbound marketing to the next level to attract potential customers. But not every sales pitch went through. As Jonah put it:

“It’s never easy to sell…some meaningful percentage of people that you talk to are still not ready to make that investment. There’s always still going to be reasons why it’s not the right timing, or they don’t have the budget.”

They key was to not get discouraged in the process. 

There were also other challenges besides conveying their brand identity when they started such as product development. Because they had to collect a massive amount of big data and use AI to analyze it, they needed to normalize all that unstructured and semistructured information coming through and enrich it so they could drive insights and action for customers. From all this data, they needed to be able to use the intelligence layer of their platform to drive strategic (long term) and tactical (short term) actions. This was very difficult.

All the hard work paid off. With their vision and software driven product in hand, they grew every year while maintaining their beliefs and values that kept them excited when they first started.

Jonah’s not tied to the past. He wants to build a revolution from the ground up, transform the industry with software, and change the conceptions people have about marketing intelligence.

Entrepreneur Advice

“Don’t do it unless you really have to. It’s not a good way to make a buck. It’s not a glamorous job for most of us. And it’s hard work. And if you think you can be happy joining somebody else’s startup or working at a big company or being a consultant or doing something else, you should do those things. And if you can’t, and you need to build a company and you need to be an entrepreneur and you think that this is your calling, then you should do it and you shouldn’t let anyone talk you out of it and you should be stubborn and bold in your pursuit of that. You really have to gut check whether this is what you want to do. And if you’re not sure, then don’t do it because it’s hard. And if you are sure, then just do it. Stop thinking about it; just do it.”

To learn more about Crayon, visit them here. To see our interview with She Geeks Out click here. If you’re interested in the most recent business secrets, check out our Business Knowledge page. If you want to stay up to date with the most recent BWS news, follow us on Instagram!