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Bootstrapping Decisively to $5M+ in Revenue: Mack Sundaram, CEO of RainmakerForce (Part 4)
Mack Sundaram: Professionally, I was working in sales, sometimes in direct sales or in supporting sales. All of that was happening on the side while I was pursuing these little things. Now we’re fast forwarding down to 2014 when I left my corporate job. I was too passionate about technology and being an entrepreneur. At
Bootstrapping Decisively to $5M+ in Revenue: Mack Sundaram, CEO of RainmakerForce (Part 3)
Mack Sundaram: Exactly. There’s always that human psychology element that tells you, “Maybe you’re not ready. Maybe you should wait another year.” That was one side of the brain holding me back. At the same time, since I’d already tasted being in a startup situation a decade before that, the lure of that novelty was
Bootstrapping Decisively to $5M+ in Revenue: Mack Sundaram, CEO of RainmakerForce (Part 2)
Sramana Mitra: I did a startup in AI 20 years ago. That was not when AI was really happening. Mack Sundaram: There you go. It was incredible to get that opportunity. It was a great experience for me. Sramana Mitra: You left the company, though? Mack Sundaram: We sold the system to the Department of
Bootstrapping Decisively to $5M+ in Revenue: Mack Sundaram, CEO of RainmakerForce (Part 1)
If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. Mack has built a successful business optimized for autonomy and profitability. Excellent navigation! Sramana Mitra: Let’s go to the very beginning of your journey. Tell us where you’re from. Where did you grow up? Where were you born and raised? Mack Sundaram: I was born in
Building a Fast-growth SaaS HR Technology Company: Justworks CEO Isaac Oates (Part 5)
Sramana Mitra: What did you learn about the target customer segment? You said you started catering to tech startups. Where was the business coming from as you grew? What were you learning about customer acquisition? Isaac Oates: There are some really big things that we learned. One is that it’s really hard to control when
Building a Fast-growth SaaS HR Technology Company: Justworks CEO Isaac Oates (Part 4)
Sramana Mitra: Who were you dialing? What was the process of targeting and positioning? Isaac Oates: I always think about what I would do differently, I would say that we probably brought on a sales team a little bit later than we could have. We had a website and people could come in and sign
Building a Fast-growth SaaS HR Technology Company: Justworks CEO Isaac Oates (Part 3)
Sramana Mitra: How did you get the company off the ground? Isaac Oates: I got a lot of help initially. It was pretty easy and there was a lot of luck involved. When I was at Etsy, one of the members of their Board was an investor. I know Danny who’s on Etsy’s Board. I told
Building a Fast-growth SaaS HR Technology Company: Justworks CEO Isaac Oates (Part 2)
Sramana Mitra: How long did you have to stay at Etsy? Isaac Oates: I was there for three years. It was pretty crazy actually. While I was there, I kept thinking about my time at Adtuitive. There were three founders and I was the one doing all of the paperwork, payroll, and insurance. I spent
