Whatfix isn’t just a company, it’s the creator of a whole new category: Digital Adoption Platforms (DAPs). But like all great founder stories, this one began with setbacks, hustle, and a bold pivot that changed everything.
From search enabler to “Fix It” to Whatfix
Like many great startups, Whatfix’s origins lie in an unexpected customer insight. Khadim and his co-founder Vara Kumar were initially building Search Enabler, an SEO tool for small businesses. But despite signing up paying users, retention was poor.
“We realised customers needed a lot more handholding, and the traditional mechanism of handholding didn’t work. So, we created a guidance button called Fix It that helped users complete tasks. People loved it and asked if they could use it for their own applications.”
That moment was the genesis of Whatfix. From a small widget, it evolved into a Digital Adoption Platform (DAP), a category that didn’t exist at the time.
Creating and owning a new category
In the early days, there was no established vocabulary for the problem Whatfix was solving.
“Some people called it an onboarding tool, some a guidance system, some in-product learning. Only later, with Gartner’s help, the term Digital Adoption Platform was coined.”
Category creation brought its own challenges from educating customers to aligning with budgets but it also positioned Whatfix as a pioneer. Today, the company powers digital adoption across 700+ customers in 40 countries, including 85+ Fortune 500 enterprises.
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Scaling Beyond a Widget: Becoming enterprise-ready
Whatfix’s journey is a masterclass in broadening scope without losing focus.
“We started as a pinpointed widget. But enterprises didn’t just want onboarding, they wanted adoption across hundreds of applications, including desktop and mobile. That’s when we became a full-stack adoption platform, even acquiring a company for mobile capabilities.”
The company also expanded into analytics and enterprise-wide insights, helping CIOs measure ROI across their massive software spends. This shift enabled Whatfix to win million-dollar deals and position itself as a strategic transformation partner.
Cracking GTM without a sales background
Both Khadim and Vara were engineers with no sales experience. Yet they built a highly effective GTM motion from scratch.
“We decided we wouldn’t build unless we had validation. Vara would give me 25-30 email IDs a day, and I’d send personalised emails with mockups. “In three months, we sent 500 emails, did 30 demos, and closed two deals – all pure outbound.”
The founders hustled through the first 15–20 sales themselves, experimenting with Google Ads, Quora answers, and events like Dreamforce to build traction. Their early learnings shaped a scalable playbook that future sales hires could follow.
From SMB to Enterprise: A conscious leap
Many SaaS startups get stuck in the SMB trap. Whatfix experimented with community-led adoption and SMB customers, but churn was high.
“For SMBs, onboarding tools are nice-to-have. But for enterprises, digital adoption is a must-have. So, we made a conscious decision to move upmarket, even if it meant giving up smaller deals.”
The company narrowed its focus to HR and sales platforms like Salesforce and SuccessFactors, finding repeatability with enterprise buyers.
“The narrower you are in terms of geography, persona, and use case, the faster you move.”
This discipline enabled Whatfix to scale ACVs from $50K to $1M+, with a repeatable enterprise sales motion.
Building trust with anchor customers
For a new category, credibility mattered more than price.
“Our first Fortune 10 customer paid us just $25 a month. But that logo was priceless. We squeezed that logo to every prospect and it opened doors. In the early days, it’s not about price, it’s about trust.”
That strategy of securing a few anchor customers and leveraging them aggressively helped Whatfix win enterprise trust globally.
Structuring for Scale: The role of expansions
As Whatfix grew, Khadim realised that expansion sales required a different DNA than hunting new logos.
“We thought AEs could do both, but they were transactional. We thought customer success could do it, but then value delivery suffered. Finally, we created account managers focused only on expansions. That worked.”
This organisational clarity allowed Whatfix to systematically grow within large accounts, rather than just chase new customers.
The founder’s evolving role
Khadim stresses the importance of founders letting go.
“As a founder, you’re best at zero-to-one. Once something starts working, hire experts to take it deeper. Delegate without losing control. Keep yourself free to experiment on the next frontier.”
From sales to marketing to alliances, his approach has been to personally crack new channels, then hand them over to specialists.
The AI tailwind in enterprise SaaS
On AI adoption, Khadim noted a dramatic shift in just 18 months.
“Earlier, CIOs were curious but hesitant. Now, every large enterprise has an AI task force, governance teams, and budgets. They’re experimenting aggressively in low-risk areas, and in the next 12-18 months, adoption will be very wide.”
He believes the AI era will create stronger tailwinds than the cloud shift, with startups able to scale from zero to $5M faster than ever before.
Fundraising Lessons: Matching investors to needs
Whatfix has raised over $270M, and Khadim emphasises that every round required different types of investors.
“Early on, we needed believers in the product. Then we needed GTM expertise. Later, we looked for geography-specific investors, and eventually deep-pocketed funds with CIO connects. Each round should solve your most pressing problem.”
He also stressed that investors won’t automatically add value, founders must proactively leverage them and get them to work for them.
Looking Back: What he would do differently
Asked what he’d change if starting again, Khadim was candid:
“I would have validated the right segment much earlier and saved three years. Many mistakes – premature bets, late bets, wrong bets. If I knew how to hire and align better, maybe we could have built this with 500 people instead of 800.”
Takeaway for founders
Khadim’s journey with Whatfix is a powerful case study in category creation, GTM innovation, and disciplined scaling. His advice is simple yet profound:
· Stay close to the customer.
· Narrow your focus before expanding.
· Anchor trust with a few big customers.
· Delegate as soon as possible.
· Match investors to the stage of your journey.
“Product-market fit is a moving target. As you grow, the persona changes, the buyer changes, the deal size changes. The journey never ends.”
Timestamps:
00:00 – Introduction
02:40 – Creating a Category Before It Existed
08:30 – PMF as a Moving Target
12:20 – 500 Emails & First Customers
15:50 – Why Focus on the US Market
18:40 – Fortune 10 Customer at $25
22:10 – Narrowing Down GTM
25:00 – Selling to Enterprises
30:00 – India vs US Sales Teams
37:00 – Fundraising Lessons
44:20 – How AI is Changing Digital Adoption
47:19 – Making Investors Work for You
(Disclaimer: The views and opinions expressed in this article are those of the author and do not necessarily reflect the views of YourStory.)
