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How did they do it?

It’s a question that often plagues entrepreneurs who aim to thrive in the challenging and competitive SaaS industry

But one of the best things about the web is that you can always find people who have asked the same questions before. And also those who are ready to provide answers now. 

A lot of SaaS CEOs have made it big. Fortunately, many have been vocal about their experiences and talked about the journey to success. 

So we’ve listed 11 interviews of SaaS entrepreneurs that you may find inspiring to watch and follow suit. 

#1 An Interview with Joshua Reeves, CEO of Gusto

Gusto is a cloud-based software that provides payroll, benefits, and human resources management software. It guides small businesses to process payroll, automatic tax filing, and benefits management services. In this interview, Joshua Reeves, the CEO of Gusto sits down with Julie VerHage of Bloomberg, to discuss the growth, and the changes Gusto has undergone over the years. 

Quick Takeaways

  • Gusto made a shift in its hiring process to make it more scalable and diverse. 
  • The company relies extensively on word of mouth and content marketing tactics for targeting small businesses.
  • The reason it has scaled and will continue to do so is because of its vision to solve a major pain point — to make payroll easy and hassle-free.
  • The evolution of Gusto in a phase-wise manner and the introduction of a flexible payment system.

#2 Journey from Zero to $1M ARR With David Cancel, CEO of Drift

Drift is a Cambridge, Massachusetts-based company that creates messaging software for businesses. It is certainly one of the biggest names in conversational marketing today and a live chat tool. Andrew Gazdecki, CEO at MicroAcquire sits down with David Cancel, the CEO of Drift where they discuss how Drift has reached where it is today. 

Quick Takeaways

  • Drift spent time checking whether their audience was ready for their product.
  • The company functioned entirely on an inbound marketing strategy till its first 50 customers. 
  • It greatly focused on story-telling for the brand which reduced customer-acquisition costs.
  • Once it got funded, they spent methodically in every aspect — hiring new talent, advertising, and office spaces.
  • The road ahead for Drift – the philanthropic ventures, product innovations, etc. 

#3 How They Reached $85M ARR in Revenue With Zeb Evans CEO of ClickUp

Nathan Latka interviews Zeb Evans, the CEO of ClickUp. ClickUp is a productivity platform and its customizable and proprietary features make it easy for teams that want to keep everything from design to development in one place. The interview talks about the story of ClickUp — right from its bootstrapping days to its current high with annual revenue of $85 million. It now has around 800 employees and offices across the globe. 

Quick Takeaways

  • Zeb is an advocate for bootstrapping until you get your product-market fit.
  • Hyper-focused teams have allowed ClickUp to scale its engineering product design with each team having an engineering manager, product manager, four engineers, and a designer.
  • In the initial stages, it was really the small marketing and promotion tactics that boosted ClickUp’s revenue.

#4 11 Months Before He Was Worth $5.6 Billion With Johnny Boufarhat, CEO of Hopin 

The virtual event platform, Hopin went from minimal revenue to a million dollars in three weeks in the early days of the pandemic. Since there was a lot to uncover there, Nathan Latka discusses with Johnny Boufarhat, the CEO of Hopin to understand what he did differently and how they quickly addressed the massive demand. He shares his insights on the future of the events industry and a little of Hopin’s sudden jump into hyper-growth mode. 

Quick Takeaways

  • In a time of massive demand, they learned to prioritize who to give slots to. It was to both — companies that had the budgets, and those that Hopin could support in terms of the bandwidth. 
  • Hopin had around 1200 leads a day. Out of those that booked a demo, they scheduled a group demo for everyone and gave one-to-one demos only to enterprise customers.
  • He was able to raise $7 million without any revenue and before the pandemic — just based on the potential and product design.

#5 Dive Into the Business of SAAS With Mathrubootham, CEO of Freshworks

Girish Mathrubootham, the CEO of Freshworks talks about running and moving forward with a SaaS business in a post-pandemic world. In this conversation with Shradha Sharma of YourStory, he discusses the changes in customer expectations, remote working, implementing a 360-degree view of the customer, and his entrepreneurial vision. 

Quick Takeaways

  • To establish a global presence, Freshworks removed barriers between customers and products. They made the product less confusing, accessible, and intuitive. 
  • A red ocean strategy really helped Freshworks make a name in the competitive SaaS market.
  • Girish believes in the philosophy of “Solve, don’t sell’. The idea is to reassure customers and reconnect in order to redesign and help them in the best way possible even in a time of crisis.

#6 Growing & Scaling SaaS Businesses from $1M to $500M in ARR with Karen Peacock, CEO of Intercom 

In a standout session featuring a conversation between Byron Deeter, Partner at Bessemer Venture Partners, and Karen Peacock, Intercom COO & Former SVP of Small Business for Intuit, the latter talks about where your priorities should lie if you want to scale your SaaS venture. Intercom is a conversational messaging platform and has become a default modern tech stack. 

Quick Takeaways

  • If you focus on just revenue, it’s the last thing you’ll achieve. Instead, focus on value and engagement. 
  • Be very clear on the benefit you’re offering to your clients and your clients to their customers. Have clear metrics to measure the progress. 
  • Fall in love with the problem, not the solution. 
  • Understand the customer experience, the product-market fit, and the funnel before investing in marketing efforts

#7 Personal Journey Of a SaaS Founder with Nathan Berry Of ConvertKit

In this interview, Nathan Barry, Founder of ConvertKit discusses how he leveraged the SaaS marketing trends in the early days and how he nailed the ideal customer profile with Dan Martell. ConvertKit is a marketing automation tool that makes it easy for users to create simple solutions for drip email campaigns and to create easy forms. 

Fun Fact: ConvertKit went from $2000 MRR (Monthly Recurring Revenue) to $90, 000 MRR in one year! 

Quick Takeaways

  • Finding its niche helped ConvertKit make a name for itself in the competitive email marketing automation industry. It became a tool specifically for professional bloggers. 
  • Nathan extensively relied on outbound email marketing to attract customers in the earlier days. 
  • He segmented email lists and got a higher conversion rate because his emails were usually short, personal, and to the point. 
  • He later leveraged affiliate marketing and webinars to scale.

#8 Journey from Zero to $1m/ARR with Sujan Patel, MD of Ramp Ventures

Sujan Patel unravels the SaaS marketing growth strategies that have generated massive increases in traffic and revenue in conversation with Andrew Gazdecki. Sujan is a veteran SaaS marketing leader who’s helped hundreds of companies reach new avenues of growth. In addition to consulting work through his SaaS marketing agency, Web Profits, Sujan owns and operates multiple SaaS businesses, including Mailshake and Right Inbox.

Quick Takeaways

  • Because of a lack of focus on product-market fit, the business took significant time to scale. 
  • He admits that he should’ve focused on failing faster so he could pivot and modify his strategy to work on the flaws.
  • He addressed the customer pain point of being hard to use by building a product with minimal features and sleek design.

#9 Scaling Even Faster the Second Time with Lew Cirne, Founder & CEO of New Relic 

Just two years into selling his company for $375 million, Lew Cirne founded New Relic; a cloud-based software to help website and application owners track the performances of their services. New Relic is worth $6 billion today. In this interview he sits down with SaaStr and talks about why he chose to do it all over again and what he learned this time around. 

Quick Takeaways 

  • He emphasizes on acing the first-minute impression of your product to your customer.
  • Regardless of how good the product is, you need to offer your customers an incentive to prioritize their decision to purchase. It can have an immediate impact on sales. 
  • He mentions that it was easy to get started at a reasonable price point because the product was self-explanatory and easier to use compared to others. 

#10 Busting the Myths About Startup Success with Therese Tucker, CEO of Blackline

SaaStr ropes in Therese Tucker, the CEO of Blackline to share her insights into common SaaS myths and how they can hold you back. She brings forward many perspectives and challenges of growing a SaaS business and those of a female CEO. Blackline is an enterprise software company that offers scalable applications that automate the financial close and other accounting processes. It is currently worth $3 billion. 

Quick Takeaways

  • There isn’t a single playbook for success. Also, humility goes a long way. Don’t get over-hyped about yourself or your idea. 
  • Don’t think you’re on your way to creating the next big revolution in tech. Write your own story. 
  • You don’t always need funding to be successful. You need to focus on getting new customers and hiring talent strategically. 

#11 Veeva: The Biggest Vertical SaaS Success Story of All Time with Founder & CEO of Peter Gassner

Veeva is one of the biggest names in pharmaceutical and life sciences industry applications today. In conversation with Jason Lemkin, Peter Gassner shares his journey to success, the early days, and how they reached the point of a $600 million run rate within a decade. 

Quick Takeaways

  • It’s critical to set quarterly goals for the first year since this is the timeframe in which most companies fail
  • Practice self-discipline in terms of raising money
  • Revenue follows people. If you want to earn revenue down the road, you need to hire the talent now who’ll help you achieve that. 
  • The mission changes as your business grows. Its initial mission was not to go out of business in the first year and later it was to make a difference in life sciences. 

Wrapping up 

As it is evident from the interviews above, every journey is different. Every problem is different and every approach is different. The best part about SaaS interviews is that the speakers don’t tell you what to do. Instead, they share their journeys and allow you to interpret them to your understanding and use the information in the best way possible. With a ton of information at your disposal good luck on getting your SaaS business on the fast track to success. 

 

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