How Nathan Kontny Rose to The Challenge of Taking Over Highrise

On this episode of Proposify BizChat, I'm joined by Nathan Kontny. A two-time Y-Combinator alumni, creator of the writing software Draft, and CEO of Highrise, a CRM that spun off of Base Camp. Nathan posts vlogs daily on YouTube, and is a frequent writer on Medium.


What it’s about

In the hustle and bustle of business it’s easy to think that most companies, large or small, are cold, corporate, and don’t care about you as a customer.

Nathan Kontny wants to change the way business is done by making it personal. Whether it’s making an email more personal, or seeking out other business owners for advice on a product you’re working on, getting personal is the key to success for Nathan.

In this interview, I talk to Nathan about how he built a relationship over time to take over Highrise, why he believes in being flexible and adaptable, and the importance of opening up about yourself.


Build relationship over time and show your value

When it comes to gaining and retaining customers, Nathan says it’s all about building a relationship, which doesn’t happen overnight.

During the process of building his writing software company, Draft, Nathan met lots of people, one of whom included Jason Fried, co-founder of Basecamp. Although Nathan knew Draft was a company Jason would likely be interested in, given his experience with writing, he avoided giving him a hard ask.

“I wasn't asking for some formal relationship, but instead asked if he would be an advisor and chat about things. He was totally game for it, and then we had this relationship over the course of months.”

Be flexible and adaptable

If you’re working with a new product or customer, Nathan says it’s crucial you stay flexible and adapt to your customer’s expectations.

Nathan says that when he took over Highrise, he noticed the product was largely built for the CEO/co-founder, Jason Fried, and CTO/co-founder David Heinemeier Hansson, to communicate and coordinate with each other. Nathan decided to change the focus of the product when he took it over, making it more user-friendly by defining who was using Highrise, and what they were using it for.

“It's been a challenge to get to the core of who uses Highrise, why do they use Highrise? It's not people who look like Jason and David. We knew that. It was formally built for Jason and David to communicate with each other, but now it’s really become a CRM.”

By being flexible with what the product does, and adapting it for the customers using it, Nathan says it has really become a CRM for sales and for leads.


Open up about yourself and get back to one-on-one

Over the years, business has become so cut and dry, cold and impersonal. To start building stronger bonds with your customers, Nathan suggests opening up about yourself.

“Even if it's just the weather, or sometimes I try to mention that my daughter is sick, or that we had a great weekend with her. The responses that come back are awesome. I get these replies from people who thought our emails were automated, but appreciate the interaction, and they start telling me about their family. It's forming these conversations that I think we probably need to be doing more of.”

Nathan says having more of those one-on-one, open conversations with customers can take away the cold, corporate feeling of a business. By opening up to them, they will be more inclined to keep returning for your service because they feel a connection with you.

Show notes




How Nathan Kontny Rose to The Challenge of Taking Over Highrise

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