5 Big Bets That Paid Off with Freshworks Founder & CEO Girish Mathrubootham

Freshworks is a successful public SaaS company that has a humble beginning in the small town of Chennai, India. Founder and CEO Girish Mathrubootham shares five big bets that paid off as he scaled this multi-product company. 

Watch to discover Mathrubootham’s key decisions in launching and scaling a company, which include: 

• Betting on inbound while going global 
• Hiring talent when talent is hard to find
• Going multi-product early on
• Layering a sales-led motion on top of a product-led motion 
• Betting on AI and the future before it arrives

As Employee Number One, Mathrubootham knows what it’s like to hustle. He believes happiness is contagious and that there are no leaders in software who aren’t multi-product. 

Let’s dive into the five big bets he made that paid off for Freshworks and ignore the 100 bets that didn’t. 

Second-timers know the playbook and can execute against it faster. But often times, they also have a bit of healthy skepticism, a bit of baggage, from the last time. First-timers often know very little, but are baggage free. That can be very powerful.

I’ve had a chance to watch a whole cohort of SaaS first-time founders go from $1m to $10m ARR in 5 quarters or less and just been awestruck by how much better than me they are as founders, and how much better they’ve done quantitatively.  

In awe.

And yet, they/we all tend to make the same mistakes. At least, some of them.

I thought I’d catalog them. You may only make 1 or 2.  You may make all 10.  Who knows. At least, consider using this list to challenge yourself to do even better. Even if you just blew out last month and last quarter.

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So first a caveat: I know just enough about financial accounting to be dangerous.  Second caveat: I’m way, way oversimplifying things.

But with that out of the way, let’s talk just enough about financial accounting to explain why Big Tech Companies both acquire smaller ones — and do corporate VC investment.

Because in the short-term, it often costs basically close to nothing to acquire a smaller startup with cash on hand, or do a corporate VC investment.

What do I mean?  Let’s take Salesforce as an example.  It has basically $12.5 Billion in cash in the bank (cash, cash equivalents, and marketable securities) — and much more to come in accounts receivable, another $10.75 Billion.

So we’ll share much more on 2023 SaaStr Annual soon, and start editing, transcribing and publishing many of the sessions ASAP.  For now, you can watch tons of them streamed here on our YouTube.

The heart of Annual now is meetings and connections, on-site, through networking sessions, through Braindates and small workshops and more.

How did we do this year?

25,300+ direct connections made

1,600+ braindates

3,200 hours of workshops and braindates

That’s in addition to 250+ speakers across 7 stages, and over 600 direct connections made in our Meet-a-VC program. And of course, the 1000s and 1000s of more informal meet-ups, parties, 1-on-1s and more that happened all across the 3 days.

This edition of the SaaStr Weekly is sponsored in part by Booking.com

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Whether you’re just starting out in SaaS or have a successful SaaS startup, founders and startup teams can learn a lot from those who have found success in the industry through its ups and downs. 

That’s why SaaStr founder and CEO Jason Lemkin held an “Ask Me Anything” session at this week’s Workshop Wednesday, held every Wednesday at 10 a.m. PST. 

In this Ask Me Anything Part 1, Lemkin answers the questions:

1. Many VCs talk about funding, yet you’re so focused on sales. Why is that?
2. When do you know you have a good SDR or AE? 
3. How do you build high-quality content that’s consistent and repeatable?
4. Do you see any segments getting stronger in the next 12-18 months? 

Let’s find out the answers. 

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