saas.unbound is a podcast for and about founders who are working on scaling inspiring products that people love brought to you by .

I’m your host Anna Nadeina, Head of Growth for In this episode #13, we are talking with Daniel Fayle, co-founder of Chekkit ( ), an all-in-one review, messaging, and lead inbox software. Daniel shares a story of launching a product having no prior tech or startup experience, taking customer communication seriously, and building a company culture where people thrive.

(0:00:07) – Building Checkkit 

Daniel Fayle, co-founder of, an all-in-one platform making it easier to communicate with customers, collect reviews, and win leads, shares his story of how he and his co-founder, Miles, started their business. From their small town in Winnipeg, they bootstrapped their way to success. Daniel walked us through the first steps of building Checkkit, and he reveals they started with a software developer they knew who built the first app which had nothing to do with Checkkit. They had also sent off an email to a professor who connected them with an engineer. From there, they started building the platform.

(0:08:41) – Sales Channels and Personalized Cold Emails 

Checkkit, the all-in-one platform for businesses to communicate with customers and collect reviews, was able to scale up their operations from door-to-door sales to transitioning online. We explore the various channels they used, from Google Ads, Facebook, and Instagram Ads, to referral bases, cold email, white label solutions, and affiliate marketing programs. Daniel explains the unique cold email strategy they use to stand out and acquire customers at scale, as well as the product itself and how it can help local businesses get found online.

(0:22:00) – Scaling a Bootstrapped Company 

Daniel shares his story on how they grew from 4 co-founders to having a sizable team on the dev, customer support, and sales sides. He also shares how they managed to bootstrap their company and grow over 50% each year, including how they found the right talent pool for their sales team.

(0:26:14) – Bootstrapping and Working on the Business

Checkkit was able to successfully grow and scale while remaining bootstrapped. We examine the constraints this has caused the team and how they have had to be creative and detail-oriented in their growth and spending strategies. Bootstrapping has enabled us to have more flexibility in our pricing, giving us a competitive edge in the market.

(0:34:22) – Challenges, Success, and Culture 

We discuss the challenges and successes Checkkit, the all-in-one platform for businesses to communicate with customers and collect reviews, has faced while growing and scaling. Daniel shares his experience with the biggest challenge right now – keeping up with feature requests – and their biggest win – creating a culture where everyone is happy with their job and lifestyle. We also hear how they got their initial traction and how they managed to answer tough questions along the way.

(0:39:19) – New Service Offering and Inspirations 

Checkkit has decided to offer services to its customers. We examine why Checkkit has taken this approach and the feedback they have received from their customers. We also look at the most inspirational part of the business and who Daniel Fayle, one of the co-founders, would love to work with.


Head of Growth,