TeardownDay 2·12 min read

How a Chennai Startup Made Zendesk Look Expensive and Salesforce Look Slow

There's a test for whether a B2B company has actually built a brand. Not market cap. Not logo recognition. It's this: when someone from that company walks into a room, do people assume they're good before they've said a word?

Freshworks passed that test a long time ago. If you're from Freshworks, people trust your talent by default. Freshworks sitting in a far-off corner in Chennai built it — selling customer support software to small businesses around the world.

This is the story of how they got there.


A comment started Freshdesk.

I'd want you to go read the origin story from the man himself instead of me repeating it in a hundred different ways. There are a lot of takeaways on the internet about this. But for me, it is simple: the internet was powerful then, the internet is powerful now. It just knows how to do its magic.

Read the Freshdesk story here.

Long story short — one of his posts about Zendesk, the competitor, went viral. And one of the comments on that post put the seed in his mind.


In October 2010, Girish and Shan Krishnasamy — both from Zoho — quit their jobs and started building Freshdesk out of a 700 sq ft warehouse in Chennai. The initial team was six people: three developers, one designer, one QA person who doubled as customer support.

They spent eight months building before going to market. No fancy launch. No Product Hunt in those days. Just a product that worked, priced for the people Zendesk had just alienated.


Three GTM principles from their first 100 days.

01 / Your story is your first campaign.

Girish posted the Freshdesk origin story on Hacker News. The story of why he built it — the anger at Zendesk, the broken customer experience, the opportunity. It went to 30,000 visitors in 2 days and brought in 175 signups. The lesson: people don't share product announcements. They share stories. If your founding story has a villain and a reason to exist, that's your first piece of content marketing.

If you're doing this nowA LinkedIn post or Twitter thread about why you're building what you're building. Not “excited to announce.” The real version — the frustration, the gap, the thing that made you quit your job. That's the post that goes viral.

02 / Validate demand before you ship.

Before Freshdesk was even complete, they entered an AppSumo contest and got 300 signups. Proof that people wanted this thing to exist. Most founders wait until the product is perfect to show it to anyone. Freshdesk validated demand while they were still building. If 300 strangers sign up for something that isn't ready, you're probably building the right thing.

If you're doing this nowA landing page with a waitlist. A Typeform survey in a Slack community. A quick Loom demo of a Figma prototype shared in a WhatsApp group. You don't need a product to test if people want it.

03 / Your competitor's name is your first keyword.

Freshdesk won $40,000 from Microsoft BizSpark. Most founders would have spread that across category keywords — “helpdesk software,” “customer support tool.” Girish went straight for the competitor. Every ad targeted people searching for Zendesk. They got 70 customers from that one bet.

If you're doing this nowSkip “best [category] software.” Start with “[Competitor] alternative.” Someone else already did the work of creating that search volume. Ride it.

100 in 100

Customers in 100 days. From a Chennai warehouse, selling to the world.

Fun trivia

Girish understood the social media culture before we even knew it existed.

In December 2011, Zendesk's CEO Mikkel Svane called Freshdesk “a freaking rip-off” on Twitter. The CEO of a company worth billions, publicly attacking a startup that was barely a year old.

Most founders would have panicked. Or ignored it. Girish built a website. ripoffornot.org— Zendesk's accusation displayed front and center, with an open invitation for users to judge. He wrote the full story of why Freshdesk existed. Then he dug into the Twitter attacks and discovered they were coming from a paid blogger hired by the competition. He published that too.

The internet did the rest. People rallied behind the underdog. A startup in a Chennai warehouse had just turned an attack from a billion-dollar competitor into free global awareness. No PR team. No crisis playbook. Just someone who understood how the internet works before most companies had figured out Twitter.

Freshdesk's entire strategy was making Zendesk look ridiculously expensive.

They operated with a simple strategy: 40–50% cheaper and free for starters. Entry-level plans started at $15/agent/month versus Zendesk's $55. That may seem like a discount at first, but that's not it. It's a different market altogether.

For SMBs — startups, small agencies, local businesses — their freemium model was a no-brainer. You could run real customer support on Freshdesk for free, and upgrade when you actually had the revenue to justify it. Zendesk was asking you to commit before you even knew if you needed it.

Zendesk

$55/agent/mo

Cheapest paid plan

Freshdesk

$15/agent/mo

Or free. No credit card.

If you're doing this nowThe advice “don't compete on price” assumes you're in the same fight. Freshdesk wasn't. They weren't trying to win Zendesk's customers — they were building for people who were never going to be Zendesk's customers in the first place. Now think about this in the AI era. Everyone can build. The product is table stakes. So what's left? Who you serve and at what price. If the incumbents have decided a segment isn't profitable enough, and your cost structure says otherwise — that's your market. And price is how you unlock it.


Their content strategy had one job: be there every time someone searched for Zendesk.

Your content strategy should be mapped to exactly where the buyer is in their decision:

Already comparing?→ “Freshdesk vs Zendesk” comparison pages. What they charge, what we charge, what you get.

Already leaving?→ “Best Zendesk Alternatives.” The buyer has decided to switch. Freshdesk just needed to be the first result.

Just searching? → AdWords on competitor brand keywords from day one.

Not searching yet? → Free tools like Freshping (6,000 organic visitors/month, 500+ backlinks) that built domain authority quietly in the background.

If you're doing this now

  • Volume is vanity. Villain is strategy. Your competitor is your best content strategy. Build around them.
  • Start at the bottom of the funnel. Comparison pages, alternative pages, competitor keyword ads — that's where buyers already are.
  • Build free tools for domain authority. Backlinks, organic traffic, DR — all from one tool that costs you nothing to maintain.

Mental model

Defining your customer goes deeper than “SMB.”

“In 2 minutes, Browser Girl has to like the product and in 20 minutes she has to feel at home with it, otherwise she will close the window and go. When my product team wants to launch a new feature, I don't sit down and let them explain it to me. I ask them to send me the link to see if it is easy for someone to figure out on their own.”

— Girish Mathrubootham, Founder, Freshworks · YourStory interview

If you're doing this now“SMB” is a category on a pitch deck. Browser Girl is a person. Discover your person. When your entire company can picture the same person, you stop debating and start building.

The hardest business decision is not changing what works.

After the first 100 days, the first 1,000 customers, the funding rounds — most founders get the itch to “go upmarket.” Sell bigger deals. Chase enterprise logos. Hire field reps. Freshworks didn't. They stayed in the SMB lane for four more years.

The sales pitch was still the same: Zendesk charges $49–99/agent/month, we charge $29–59. That price gap was the entire sales deck. They optimised the machine instead of replacing it.

If you're doing this nowIf your current motion is working, optimise before you diversify.


Expand across the company, not within the team.

The default instinct is to keep building for the same team. More features. More use cases. More integrations. Make the support team love you even more. But that makes you one team's tool — and one reorg, one budget cut, one new manager away from being replaced.

Freshworks did it differently. Once they were in the system through support, they built for IT. Then for sales. Then for marketing. Different product, different team, different budget. Same company.

If you're doing this nowDon't build more features for the same team. Build a different product for the next team. That's how you go from being a tool to being infrastructure.

2010

Freshdesk

Customer support. Took on Zendesk. 100 customers in 100 days.

2014

Freshservice

IT service management. Took on ServiceNow. $1M revenue in 10 months. 3x ARPU of Freshdesk.

2016

Freshsales

CRM. Took on Salesforce. The #Failsforce blimp came two years later.

2017

Rebrand → Freshworks Inc.

Freshchat, Freshcaller, Freshmarketer. The name Freshdesk was limiting what they could become.

2021

NASDAQ IPO

$13B valuation. 62% revenue from existing customers. $50K+ ARR accounts doubled in 2 years.

Fun trivia

Freshworks made going after the biggest names in the room their identity.

In 2018, during Salesforce's annual Dreamforce conference, Freshworks flew a blimp over Salesforce Tower with “#Failsforce” printed on it. Organized a marching band. Set up a pop-up space. Bus ads. Billboards. A Chennai company trolling a $100B+ enterprise giant at their own event.

#Failsforce blimp over Salesforce Tower during Dreamforce 2018

Source: Twitter / @freshworks

Some fun campaigns to watch.

Freshworks is one of the most important GTM stories to come out of India. Not because everything went perfectly — but because the playbook they wrote in 2011 is still relevant for anyone building a SaaS company from here today. The specifics change. The principles don't.

Your Homework

Apply the Freshworks playbook to your product. Brutally honest:

  1. 1VILLAIN: Who's your Zendesk? The incumbent your buyer is frustrated with.
  2. 2FOUNDING STORY: Write the version that has a villain, a frustration, and a reason to exist. One paragraph.
  3. 3PRICE ENTRY: Is there a segment the market leader has priced out? That's your entry.
  4. 4BROWSER GIRL: Who's your Browser Girl? Not the segment — the person. Name them. What do they do in the first 2 minutes with your product?
  5. 5BUYER JOURNEY: For each stage — comparing, leaving, searching, not yet aware — do you have a page?
  6. 6ECOSYSTEM: What's the second product that would make it painful for your customer to leave?

If any of these are blank, that's where the work starts.

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