Because the birthdate of Montagna is unknown, there is also debate as to when exactly he began his career and how old he was at the time. Throughout his career, his works are characterized by a simple, laconic nature. His figures often appear solemn and plastic in form. His first known documented commission was for two paintings for the Scuola Grande di San Marco in Venice. The paintings were contracted to depict the Deluge (flood myth) and another scene from Genesis, however their final status is unknown as they were destroyed in a fire in 1485. The next known record of Montagna's work is for an altarpiece in the hospital of Vicenza, of which the current whereabouts are also unknown. His first extant painting is from September 1487 (as inscribed on the back of the work) for a painting of The "Virgin and Child with Saint Sebastian and Roch". A small work intended for private use, it depicts the figures in a marble enclosure with a Vicentine landscape in the background. This painting also shows Montagna's first known use of trachyte marble, a unique texture of marble, which is seen in most of his works. Around this time, he was also commissioned to do the high altarpiece of San Bartolomeo of Vicenza, of which the exact date is often debated. This shows influences from multiple works of Giovanni Bellini located Venice that are also undated. In 1490 he painted an altarpiece for the Certosa di Pavia in Padua showing the "Virgin and Child Enthroned with Saint John the Baptist and Jerome". In 1491 he painted the altarpiece, the semi-dome, and other wall frescos for the oratory dedicated to St. Blaise at the church of Santi Nazaro e Celso in Verona. The semidome depicts St. Blaise with companions and the walls depict other scenes from the legends of St. Blaise. These works are noted for their realistic gaunt figures. From 1497-1499 he was paid monthly to work on an altarpiece for the Squarzi family. His final payment was in the form of a piece of property which he kept until 1503. This was located in a chapel in the Church of San Michele and entitled "Madonna and Child Enthroned with Saints". The outlines of this painting are very bold compared to his other works and it features detailed drapery. His early works are generally characterized by the use of trachyte marble architecture and a particular positioning of the Virgin's hand, showing the middle and ring-finger touching and widely separated from the index and pinky finger.