From Solo Developer to Venture Scale Entrepreneur: Jordan Boesch, CEO of 7shifts (Part 4)

Sramana Mitra: In terms of marketing and customer acquisition, was Google search still yielding for you?

Jordan Boesch: Yes. If you searched for something as basic as restaurant scheduling software, there’d be no organic relevant results. We thought this was a great opportunity to build content around these keywords. We didn’t have a ton of money to spend on Adwords. We were very careful about that.

Bootstrap First, Raise Money Later and Build a World-Class AI Startup from India: Raghu Ravinutala, CEO of Yellow.ai (Part 5)

Sramana Mitra: What is your relationship with companies like Zendesk and Freshworks?

Raghu Ravinutala: I call it frenemies. We integrate with Zendesk. Any transfer is handled by Zendesk. We have a lot of cases where we have replaced Zendesk as well. In some cases, we do compete with handling the same budget out there. The biggest thing I talk about is Salesforce as an investor in the company.

From Solo Developer to Venture Scale Entrepreneur: Jordan Boesch, CEO of 7shifts (Part 3)

Sramana Mitra: Were your other co-founders technical?

Jordan Boesch: My wife is not technical. She was doing client success, sales, and business development. I was doing design and web development. Our third co-founder was doing the mobile apps.

Sramana Mitra: How did you find him?

Bootstrap First, Raise Money Later and Build a World-Class AI Startup from India: Raghu Ravinutala, CEO of Yellow.ai (Part 4)

Sramana Mitra: How developed are your system-integrated channels? The kinds of things that you’re talking of doing, this is the kind of thing system integrators do well, right? You have talked about customer support use cases. You talked about IT support use cases and HR support. If you went into an enterprise, you could do millions of dollars of business in each enterprise. Are you penetrated into that channel?

Raghu Ravinutala: Yes, I talked about Roche Pharma. That’s a joint win with Accenture. It’s deployed by Accenture. We have deals with Infosys. India’s largest government implementation, which is for India’s income tax, runs automated servicing for their customers and is completely handled and deployed by Infosys on top of our platform.

From Solo Developer to Venture Scale Entrepreneur: Jordan Boesch, CEO of 7shifts (Part 2)

Sramana Mitra: Beyond your dad, how did other customers find you?

Jordan Boesch: We had it online and people were finding us because they were just looking for scheduling software. They would google us and they’d sign up. I didn’t think anything about how to expand and get more. It was really just a fun project for me where folks could sign up and I could talk to them and learn about their needs. That’s how people found us.

Sramana Mitra: How much were they paying?

Bootstrap First, Raise Money Later and Build a World-Class AI Startup from India: Raghu Ravinutala, CEO of Yellow.ai (Part 3)

Sramana Mitra: What are the numbers on Series B and Series C?

Raghu Ravinutala: In series B, we raised about $20 million. In Series C, we raised about $79 million.

Sramana Mitra: That’s a lot of money that you’ve raised. You’d have to build a huge company to return that investment. One of the things I’m hearing from a lot of enterprise startups that sell to the enterprises is that it has become easier to sell to the international market because buyers have become used to evaluating and buying online. Are you experiencing that as well?

From Solo Developer to Venture Scale Entrepreneur: Jordan Boesch, CEO of 7Shifts (Part 1)

Jordan started as a solo entrepreneur in a small province of Canada, Saskatchewan, and has built a heavily funded, high-growth SaaS business. Fascinating journey!

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, and raised, and in what kind of background?

Jordan Boesch: I’m from Saskatchewan, a province in Canada. I’m the CEO at 7Shifts which is a team management platform. Before 7Shifts, I was a software developer for many years. I ended up working for my dad who ran some Quiznos locations.

Bootstrap First, Raise Money Later and Build a World-Class AI Startup from India: Raghu Ravinutala, CEO of Yellow.ai (Part 2)

Sramana Mitra: You got to a million ARR on the strength of those first 10 customers?

Raghu Ravinutala: No, once we got the 10, we got more. When we were at $1 million, we had 35 to 40 customers.

Sramana Mitra: You didn’t have to raise money until that point?

Raghu Ravinutala: Correct.

Sramana Mitra: How many people were you then?