Scaling Your SaaS Subscriptions and Billing

0:00Loading…

Listen on:

Like this episode?

Get real founder strategies for the AI era. Delivered weekly.

Free weekly newsletter · No spam

Krish Subramanian the co-founder and CEO of Chargebee, a platform that automates subscription management and billing for SaaS and e-commerce businesses.

Chargebee was founded in 2011 and is based in Chennai, India. To date, the founders have raised $6 million in funding but bootstrapped the business for the first year and a half.

We talk about the challenges faced by businesses in managing their SaaS subscriptions and recurring billing scenarios. And we explore how Chargebee is solving those problems and helping SaaS businesses to reduce customer churn.

The founders knew that they wanted to work together, but it took them 10 years to save enough money and have the courage to finally take the leap and quit their jobs.

And then it took them over a year to launch their MVP because they tried to build too many features. We talk about the lessons they learned from this experience and how they'd do things differently now.

We also explore what it's like to build a SaaS business in India. You don't have the benefits of being in Silicon Valley and you're trying to convince SaaS and e-commerce businesses around the world to manage their revenue with your platform. And they faced a lot of resistance and challenges along the way.

We talk about how they overcame those challenges and what they've done to get over 6000 companies around using their platform.

This episode is part of our Bootstrapping series.

More on Bootstrapping

Adam Fard, UX Pilot

Bootstrapped SaaS: From Agency to $5M ARR in 2 Years

Adam Fard is the founder of UX Pilot, an AI platform that helps product design teams create and ship great user experiences faster. In 2023, Adam was running a successful UX agency when ChatGPT and LLMs started taking off. He began experimenting with ways to apply AI to his team's design processes and built a Figma plugin that helped users work through UX frameworks and activities. Then during a user interview, someone asked a simple question: "I have all these ideas on my canvas, but can I turn them into something visual? Can I create a wireframe?" That question stuck with him. He started looking around to see if any tools could actually generate wireframes from text input. He found a few products claiming to do it. But when he tested them, he realized they were faking it. They were just swapping existing templates and personalizing the copy. None of them could truly generate a layout from scratch. There was a technical reason for that. Creating wireframes with AI was genuinely hard. So Adam started working on it himself. He explored fine-tuning LLMs, hired AI researchers, and tested component-based approaches. He spent four or five months iterating. Slowly, things started working. The outputs became stable enough to use. He added Figma integration so designers could bring wireframes into their existing workflow. Within six or seven months of that original user question, UX Pilot hit $10K MRR. But growth created a new problem. Adam hired too slowly. At $30K MRR, he kept questioning whether this was the ceiling. He added one engineer, waited, added another, waited again. Looking back, he says he should have hired five people at once instead of dragging out the process. Today, UX Pilot generates over $5 million in ARR with a team of 30 and over 15,000 paying subscribers. All bootstrapped. In this episode, you'll learn: - Why Adam initially said he didn't want the product to focus on AI generation, and what changed his mind a few months later - How he validated the wireframe generation opportunity by testing competitors and discovering they were all faking it - What happened when Google suddenly deranked all of UX Pilot's landing pages, and how he recovered - Why talking about product updates in his newsletter drove more engagement than traditional educational content - How focusing narrowly on design (instead of building another no-code tool) became their biggest competitive advantage

James Ashford, GoProposal

Bootstrapped SaaS to 8-Figure Exit (No VC, No Problem)

James Ashford is the founder of GoProposal, a proposal and pricing platform for accountants which he bootstrapped and sold for an 8-figure sum. James didn't have a tech background. He wasn't an accountant. And he'd never built software before. But he noticed something broken: accountants couldn't price their services. They'd guess fees based on what the last client paid. Proposals took days. Deals fell through because people got busy. So he built a simple solution. A digital menu that let any staff member price and close deals in 15 minutes. The first version? A WordPress plugin that cost £4,000 to build. Before writing a single line of code, James did something unusual. He calculated how much money he needed to never work again (£5 million), identified the companies that might acquire his business (Sage, Intuit, Xero), and printed their logos on his wall. This wasn't optimism—it was his bootstrapped SaaS exit strategy from day one. To crack the accounting industry as an outsider, he traded 10% of his software company for 10% of an accounting firm. Instant credibility. Then he wrote a book in two weeks, made it an Amazon bestseller, and used it to build a waitlist of hundreds before launch. His marketing philosophy was simple: market like a celebrity chef. Gordon Ramsay shows you how to cook his recipes for free. You still go to his restaurant. James gave away everything—the methodology, the frameworks, the exact playbook. People still bought the software because they wanted it done faster. The bootstrapped SaaS approach forced creativity. When he realized a single conference cost £25,000, he hired a full-time videographer instead. Twelve months later, the pandemic hit. Competitors who relied on events were stuck. GoProposal dominated online. By the time he sold, GoProposal had over 1,100 customers, a 78 NPS score, and playbooks for every single process in the business. Three potential acquirers approached him within months of each other. The exit price? 8 figures. The multiple? One he still doesn't publicly share because it was "crazy."

Sam Darawish, Everflow

Bootstrapped SaaS to $30M ARR: Why Scarcity Forces Focus

Sam Darawish is the co-founder and CEO of Everflow, a partner-marketing platform that helps companies manage their affiliate programs, influencers, and performance-marketing campaigns. Sam started in online marketing in the early 2000s, working at one of the first affiliate and pay-per-click companies in San Francisco. When the iPhone launched in 2008, he and his two co-founders saw a chance to bring what they had learned from desktop to mobile. They bootstrapped Moola Media, one of the first mobile affiliate networks, and built their own tracking platform because there were no good third-party options for mobile at the time. In 2013, Opera acquired Moola Media for $50 million. During the three-year earn-out, Sam kept hearing the same complaint from marketers: no one liked the existing affiliate-marketing software. When the earn-out ended in 2016, the founders invested a few hundred thousand dollars of their own money into Everflow and did not pay themselves for the first couple of years. The first six to seven months of their bootstrapped SaaS journey were spent talking to potential customers and refining ideas. Then they decided to go all in at Affiliate Summit in Las Vegas, renting a booth with nothing more than screenshots of the product. Two prospects from that conference became their first paying customers—even though one made them sign an agreement to take over the software if the company failed. By early 2018, the bootstrapped SaaS hit $1M ARR with just 10 people and turned profitable. Today, Everflow has grown to nearly $30M ARR with 1,200 customers and 120 team members across San Francisco, Montreal, Amsterdam, and Dubai—all without raising external funding.

←All Episodes

Scaling Your SaaS Subscriptions and Billing

Links

More on Bootstrapping

Bootstrapped SaaS: From Agency to $5M ARR in 2 Years

Bootstrapped SaaS to 8-Figure Exit (No VC, No Problem)

Bootstrapped SaaS to $30M ARR: Why Scarcity Forces Focus