SaaS Interviews with CEOs, Startups, Founders – Details, episodes & analysis

Tim founded SaaS Group in 2018 using his own money from Eyeo exit to acquire Deploybot. SaaS Group is structured as an LLC and funded all deals with equity until 2020 when they began using debt. In 2024, they sold about 5% of the SaaS Group LLC for $25m implying a value of $500m. They’ve purchased 20 companies over the last 5 years. Their companies do $60m in combined revenue today and employ 300 people. They typically pay 2-4x multiples. DashThis, Usersnap, and Rewardful are some of their larger companies. Can they acquire $60m more in ARR over the next 12 months?

Constellation software just bought this company after the bootstrapped CEO hit 60% yoy growth and over 200 paying customers. The company did 30% EBITA margin last year and is now part of Constellation Software Juniper Group. 

Kate Bradley Chernis is the Founder & CEO of Lately, which uses AI to automatically transform longform content like blogs, podcasts and videos into dozens of ""smart"" social posts it learns will yield the highest engagement from your audience. As a former marketing agency owner, Kate initially created the idea for Lately out of spreadsheets for then-client, Walmart, and got them a 130% ROI, year-over-year for three years. Prior to founding Lately, Kate served 20 million listeners as Music Director and on-air host at Sirius/XM. She’s also an award-winning radio producer, engineer and voice talent with 25 years of national broadcast communications, brand-building, sales and marketing expertise.

Derek Steer is the CEO of Mode, a new startup enabling data scientists to share and discover work. With Mode, analysts are more productive and connected, both publicly within the data community and privately within organizations.Before co-founding Mode in 2013, Derek was an early member of Yammer’s Analytics team. There, he built tools to identify strong leads and customers at risk of attrition within a pool of freemium users. Derek has also worked in antitrust economics and on the Monetization Analytics team at Facebook.

Anne-Laure Le Cunff is the founder of Ness Labs, an online platform offering neuroscience-based content and coaching to thousands of entrepreneurs and knowledge workers. Prior to Ness Labs, she led marketing for digital health products at Google. She holds a MSc in applied neuroscience from King's College London.

Former banker & 2nd time founder, Keren Moynihan is the CEO/co-founder of Boss Insights. Boss Insights offers Business Data as a Service. Their single API enables easy access to hundreds of sources (Quickbooks, SalesForce, Stripe) bridging data gaps between banks and business customers in under 1 minute. Banks know where a business was, is and will be on demand. Keren has 15+ years' experience in financial services as a banker, advisor and is on the Commonwealth’s Women Invested Advisory Council. Under her leadership, Boss was awarded the 2020 Unicorn Challenge and 2019 Executive leader in lending, featured in Forbes, ABA and The Financial Brand for saying Banks must adopt APIs or Fintechs will win.