The SaaS Podcast: Founder Interviews - Page 6

John Li, Vimcal

70% Close Rate: The 4-Step SaaS Onboarding Call Framework

In 2017, John Li and his co-founder Michael got accepted into Y Combinator with an augmented reality idea. The market was not ready. They pivoted to a fitness app. That did not get traction either. After two years and two failed products, they had eight months of runway left. In 2019, they bet everything on their third idea: Vimcal, a calendar app designed to be the fastest scheduling tool for busy founders, VCs, and remote teams. But building a calendar app proved harder than expected, and by launch day they had just 1.5 months of cash remaining. They had already prepared legal documents to shut down the company. John's survival tactic was SaaS onboarding calls. He got on a 30-minute Zoom with every single user, perfected a demo script, and asked for a $15 subscription at the end of each call. His close rate hit 70%. When users matched the qualifying profile of using Calendly, Google Calendar, and Superhuman, the close rate jumped to over 90%. One of those SaaS onboarding calls changed everything. A user offered to write a $5,000 investment check instead of paying $15. More checks followed. John used the calls as both a conversion tool and a fundraising vehicle during the early months of COVID, when no one else was writing checks. John also built a waitlist with a Typeform that acted as a qualifying filter. Of tens of thousands of signups, Vimcal only let in about 20%. The first question asked whether the user felt overwhelmed by meetings, and 92% said yes. Qualifying questions about which apps they used and how many external meetings they had determined who got access. The company later stumbled when it dropped both the waitlist and the onboarding calls on the same day. Growth slowed for six to eight months until they rebuilt momentum by shipping every two weeks, landing a TechCrunch feature, and reintroducing onboarding call prompts in the self-serve flow. Today, Vimcal is a nine-person team that has raised $2.4M and is targeting $1.5M ARR with profitability in sight. John also launched Vimcal Maestro, the first calendar built specifically for executive assistants.

Richard Fenton, Go For No

Why the Best Startup Sales Strategy Is to Hear No More Often

Richard Fenton is a speaker, coach, and co-author of the bestselling book "Go for No!" alongside his wife and business partner Andrea Waltz. His latest book, "When They Say No: The Definitive Guide for Handling Rejection in Sales," builds on that foundation with 41 practical strategies for handling rejection. Richard's path to becoming a startup sales expert started with complete failure. Working for his father - a legendary car salesman who was the number one seller of General Motors product in company history - Richard sat frozen at his desk for 30 days, unable to make a single cold call. Fear of rejection paralyzed him completely. After quitting and moving from Chicago to Los Angeles to escape his father's shadow, Richard took a retail job selling suits. He failed again. That is, until a district manager named Harold asked him a career-changing question after a $1,100 sale: "What did that customer say no to?" The answer was nothing. Richard had been cutting customers off at his own mental spending limit instead of pushing for the next yes. That conversation rewired Richard's approach to startup sales entirely. He stopped treating "no" as the enemy and started treating it as a metric to increase. Within a year, he became an award-winning salesperson. He went on to build a business coaching Fortune 500 companies - including a seven-year pursuit of Discovery Network that finally resulted in a deal. Richard's philosophy applies directly to SaaS founders. Whether you are making outbound calls, running demos, or pitching investors, the fear of hearing "no" causes most founders to undercharge, under-pitch, and leave deals on the table. One of Richard's earliest clients told him to raise his prices because they were so low it raised doubts about his credibility. In this conversation, Richard breaks down why quantity of presentations beats quality when it comes to startup sales, how to use rejection as a diagnostic tool, the concept of becoming an "assistant buyer" to your prospect, and why building long-term relationships through value-driven follow-ups is the fastest path to closing deals.

The SaaS Podcast

How SaaS Content Marketing Built an 8-Figure Business

From Nice to Have to Must Have: Repositioning a SaaS Product

Horizontal Product, Zero Focus, Then 100 Customers in 100 Days

He Waited 10 Years to Launch - Then Grew 400% Year Over Year

How a Weekend Data Analysis Closed an Enterprise Deal

Why Your SaaS Product Design Fails Without Wireframes

How Sitting in Back Offices Built a Vertical SaaS

2 Years of Discovery Before Writing a Line of Code

From 60% Churn to Zero - How Howwe Fixed SaaS Retention

5 Lessons on Finding Product-Market Fit and Scaling

From Services to SaaS by Selling One Customer for 2 Years

70% Close Rate: The 4-Step SaaS Onboarding Call Framework

Scaling SaaS With No Sales Team Using Automation

100 Interviews Before Code: Finding Product-Market Fit

11 Years Bootstrapped Then Funded to Build Enterprise SaaS

Competing with DocuSign by Being 10x Easier to Use

Outbound B2B SaaS Sales That Drove 90% of Revenue

Scaling SaaS With Unit Economics, Not Just Growth

How Grain Found Product-Market Fit After Throwing Away a Year of Code

Why the Best Startup Sales Strategy Is to Hear No More Often

From $5K MRR to Tens of Millions Scaling SaaS Without Funding

29x ARR Growth Started When the CEO Sold the Product Himself

The SaaS Go-to-Market Playbook That Signed 250 Customers

How SaaS Content Marketing Built an 8-Figure Business