Kristin O'Leary - NexChapter

KRISTIN O’LEARY

Co-Founder & COO

Kristin is the co-founder and former COO of Sonapay (SONA), where she built and ran the operational engine behind one of Canada’s most respected merchant services brands. A CAIB-certified insurance broker turned entrepreneur, Kristin previously acquired and successfully exited her own business before joining SONA full time. She is the integrator to Ryan‘s visionary — the steady hand who kept the business, the family, and the mission on track through eight years of bootstrapped growth. She is now co-steering the family’s next chapter, including a global sailing circumnavigation in 2028.

LinkedIn: https://www.linkedin.com/in/kristin-o-leary-34176115b/

07 ft. Ryan O’Leary & Kristin O’Leary

HUSBAND AND WIFE BUSINESS, BUILT TO SAIL

Ryan and Kristin O’Leary, husband and wife co-founders of Sonapay, join Raman Sehgal to unpack how they built, scaled, and sold a bootstrapped Canadian payments business. They explore the risk of going all in with four kids at home, the power of residual revenue and values-led selling, the reality of burnout and earn-outs, and how a dream written into their wedding vows became the compass for life after the exit.

KRISTIN O’LEARY

FEATURED ON

HUSBAND AND WIFE BUSINESS, BUILT TO SAIL