Enter beneath an expensive incumbent's pricing umbrella with a simpler product, let it acquire users cheaply on its own, then expand revenue by selling that base an ever-broadening suite.
Freshworks
Freshworks is an Indian SaaS company founded in Chennai in 2010 by Girish Mathrubootham and Shan Krishnasamy, and taken public on Nasdaq in 2021. It began as Freshdesk, a cheaper and simpler answer to Zendesk in customer support, then broadened into a suite spanning CRM (Freshsales), IT service management (Freshservice), and marketing (Freshmarketer). The through-line: undercut an incumbent that could not respond, acquire customers cheaply through the product itself, then grow account value by selling them more of the suite.
Counter-Positioning: entering under Zendesk's price umbrella
The problem. In 2010 the SaaS customer-support market was defined by Zendesk, an incumbent whose product was polished but increasingly expensive and enterprise-oriented. The trigger was a Hacker News thread about Zendesk raising prices (reported in the range of 60% to 300%), where one commenter wrote that someone could come along with the right product at the right price and take all of Zendesk's customers away. Mathrubootham, then a product manager at Zoho, saw both an angry installed base and an incumbent boxed in by its own price point.
The approach. He built Freshdesk as a deliberately simpler, cheaper, easier-to-adopt help desk positioned directly beneath Zendesk's pricing. The counter-position was structural: Zendesk could not slash prices or radically simplify without cannibalizing the higher-priced, enterprise revenue its investors valued, so the low end was Freshworks' to take. Freshworks even leaned into the moment, publicly courting Zendesk's disgruntled users and offering to match the remaining value of their Zendesk contracts.
How it solved it. The affordability wedge worked: Freshworks grew into a platform serving more than 50,000 customers by its 2021 IPO, and priced its Nasdaq debut on September 22, 2021 at $36 per share, raising roughly $1 billion at a valuation around $10 billion. The incumbent it had positioned against, Zendesk, never managed to displace it from the SMB tier it had claimed.
Land and Expand: from one help desk into a multi-product suite
The problem. A single support product, sold cheaply to small businesses, caps revenue per account and leaves growth hostage to constant new-logo acquisition. To build a durable business, Freshworks needed to grow the dollars inside accounts it already had, not just add more of them.
The approach. Freshworks extended beyond Freshdesk into adjacent products (Freshsales for CRM, Freshservice for ITSM, Freshmarketer for marketing), so an existing customer could adopt a first product and later buy more. This is a classic land-and-expand motion: land with an affordable entry product, then expand through cross-sell and seat growth within the same account.
How it solved it. The S-1 showed the model working. As of June 30, 2021, net dollar retention was 118%, meaning existing customers spent 18% more year over year even before counting new logos, and about 18% of customers had purchased two or more Freshworks products. In the first half of 2021, a majority of revenue growth came from existing customers rather than new ones, and 13,300 customers were each contributing more than $5,000 in annual recurring revenue.
GTM: inbound and self-serve instead of an enterprise sales army
The problem. Selling a low-priced product to tens of thousands of small and mid-sized businesses cannot support the cost of a traditional enterprise field sales force. Freshworks needed a distribution model where acquisition cost stayed small relative to a modest average contract value, and it was doing this from Chennai, far from most of its buyers.
The approach. Freshworks built a product-led, inbound go-to-market: SEO-driven content, listings on peer-review sites, paid digital campaigns, and free trials (typically around 14 to 21 days) funneling prospects into a self-service onboarding where the product itself drives conversion. Direct sales was reserved for larger mid-market and enterprise deals, not the SMB base.
How it solved it. This low-touch engine let a Chennai-based company sell globally at scale, reaching over 50,000 customers and growing revenue to roughly $371 million in 2021 (up from about $250 million in 2020), with revenue in the first half of 2021 climbing to $168.9 million. The efficiency of inbound acquisition, rather than expensive outbound sales, is what made an affordable, high-volume suite financially viable.