Generating 38x ROI via AI with Matthew Tillman CEO of OpenEnvoy

Matthew Tillman is the CEO of OpenEnvoy and has worked in the machine-learning space for over 20 years. Matthew talks to Ryan about how he built his solution to generate 38x ROI for his customers, where to spend your time in your start-up as well as machine learning and the role of AI in reimagining what is possible.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  

Explore becoming Superhuman here:


  • OpenEnvoy replaces complex accounts payable processes by replacing human-centric workflows with AI.
  • One of the ways to overcome many go-to-market challenges is to hire a team that has the right skills to both create value and demonstrate it effectively to your customers.
  • Matthew recognised there was a problem in the accounts payable industry as none of the companies could handle variable cost invoices, so he set out to fix it.
  • As a founder, you have to recognise what things are worth delving into deeply and what ideas and thoughts need to be put ‘on the back burner’. It can be too easy to investigate and get involved in anything to do with your business as you have so much passion for it.
  • Focus on your business and what you can do more of today to grow it.
  • Customer feedback is always an opportunity, the information you get is invaluable.
  • Think about which people can add value to your business but also who you as a leader and founder can add value to, to get the most out of your people.
  • Focus on the customers who will love you and therefore will refer you, this is one of the least optimized customer acquisition levers.
  • Machine learning and tech are so much cheaper, in many cases even free. This wasn’t possible 20 years ago; it has democratised many industries.
  • Opensource tech means you get an incredible amount of feedback whilst having to provide a lot less value.
  • Matthew believes that AI gives us the opportunity to stop treating humans like robots, finding solutions to help find them value-add work to do instead of treating people poorly.
  • Demonstrating a 38x ROI for his customers proves that the OpenEnvoy solution is providing incredible value.


“All founders have to be insanely passionate about whatever they’re working on”

“I love hearing from customers, good or bad”

“It’s really important to nail your schedule”

“You optimize towards customers that will love you and refer you”

“The reality is machines do this black and white input better than you can handle it”

Ryan Staley

Founder and CEO

Whale Boss 


Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo:

This show was brought to you by Progressive Media