He thereafter worked as the Deputy Chief Executive Officer, Higher Education Loans Board before being promoted to serve as the CEO of the same institution.
His popularity and landslide victory is majorly credited with his track record while he was the chief executive officer of the Higher Education Loans Board (HELB).
In the April 2022 UDA Party nominations, he beat the incumbent Governor Stanley Kiptis where is making his comeback to the leadership of the county upon clinching the seat in August 2022.
In his campaigns, Cheboi promised to tackle cattle rustling, boost food security through initiation and rehabilitation of irrigation schemes and promote education in the county.
Governor Cheboi and Senator Gideon Moi, though elected through different political parties have exhibited a close working relationship for the sake of development of Baringo County.