Bootstrapping World Class SaaS Expansion to 140% NRR with FORBES IT Council Member Jay Hakami

Jay is the founder and CEO of SkyPad, a SaaS company which bridges the data gap between retailers and brands. He joins Ryan to talk about his world-class expansion techniques that have built SkyPad to over 140% NRR plus over $10 Million in ARR. He gives the lowdown on his growth path and the core metrics he and his team focus on.


  • SkyPad had significant growth throughout the pandemic and is looking at around 35% growth going into 2023
  • The primary go-to-market strategy is expanding to meet the needs of their customers via new solutions and products
  • Investing in technology is one of SkyPads strategies but they still recognise the need to expand their team with talented people; you need those who can generate ideas for continuous innovation and development.
  • Customer input is essential to building software that works for your clients and remains to be successful.
  • Before their great growth, SkyPad did spend some time in the red, surviving with funding from their own reselling business.
  • An aggressive marketing strategy towards existing clients, as well as the retail community, is one of the ways SkyPad exponentially grew.
  • SkyPad has an incredible close rate on their demo, 75%, so the key for them is to simply get in front of prospective clients.
  • MRR is a key component for SkyPad, it is one of the core metrics they focus on alongside the churn and the team that make it happen.


 “What we’re doing is special, it’s essential”

“You don’t want to sit there and develop in an ivory tower, you want customer input”

“They send us all the data and we do the distribution”

“We have very large companies using SkyPad”

“Most important are the team, the people behind it”

Do You Want The Closing Secrets That Helped Close Over $125 Million in New Business for Free?”  Grab them HERE:

Ryan Staley

Founder and CEO

Whale Boss




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