
The Road to OnRamps
At OnRamps, we're driven by a belief that first impressions matter. There are so many things that you can't control for, but as leaders, creating meaningful experiences that connect, clarify and build community are within your control.
As former educators and start up leaders, building systems and creating community is in our DNA. OnRamps combines detail orientated planning with big picture strategy to create extraordinary experiences.
About Us

Carli Gribov is the cofounder of OnRamps and a seasoned leader at the intersection of leadership development and people operations. Before launching OnRamps, she served as VP of People Operations at a PE-backed real estate startup, driving onboarding, performance management, talent development, and recruitment during a period of 120% growth.
Previously, Carli spent over a decade at Teach For America, culminating in her role as head of the National Recruitment Team, where she led TFA’s efforts to recruit 5,000 teachers annually and designed onboarding programs to prepare educators for success in challenging environments. She began her career teaching 5th-grade science through Teach For America in Houston, TX. As a leadership coach with the organization, coached hundreds of teachers and built the first iteration of TFA’s signature values based leadership development program.
Carli holds a degree from the University of Michigan and is a certified executive coach (PCC) through the International Coaching Federation.

Cailie Ryan is the co-founder of OnRamps and a human-centered senior operator and builder. She has over 14 years of experience in leadership development, team building and scaling high-growth start-ups.
Prior to OnRamps, she spent 6 years as Head of Ops at a VC funded EdTech startup, growing the company from pre-revenue to 1300 school unit customers while overseeing nearly half the company and all business lines. Cailie started her career as a Corps Member in Teach for America Chicago. After her teaching experience, she joined TFA Chicago staff and worked as a Leadership Development Coach, supporting hundreds of teachers to build the skills needed to be successful in the classroom, while preparing them for career opportunities post their teaching commitment.
Cailie holds a degree from Northwestern University and has a passion for unleashing leaders to achieve greatness through shared expectations, clarity on goals and building strong processes and communication to get there.