Shkop married a niece of Eliezer Gordon, and in 1884 was appointed a rosh mesivta at Telz Yeshiva, where he remained for 18 years. While there, he developed a system of Talmudic study which combined the logical analysis and penetrating insights of Chaim Soloveitchik with the simplicity and clarity of Naftali Zvi Yehuda Berlin and which became known as the "Telz way of learning". In 1903, he was appointed rabbi of Moltsh, and in 1907 of Bransk. Among his students in Moltsh was Yechezkel Sarna, who studied under Shkop for a year in 1906, before leaving to the Slabodka yeshiva when Shkop himself left. During World War I, the communal leaders urged him to leave before the Germans arrived, but he refused and stayed with his community.
Grodno
Between 1920 and 1939, at the request of Rabbi Grodzinski, he succeeded Rabbi Alter Shmuelevitz as Rosh Yeshiva of the renowned Sha'ar HaTorah in Grodno. He raised the level of the institution and transformed it into one of the finest yeshivos in Poland and beyond. Hundreds of young men flocked there from near and far. One of his students there was Rabbi Dovid Lifshitz, later to become the Suvalker Rav. For many years, Rabbi Zelik Epstein, who was married to a granddaughter of Rabbi Shkop, has headed a successor institution in Queens, known as Yeshiva Shaar Hatorah - Grodno. When he was eighteen, Chaim Shmuelevitz was invited by Shkop to give the third level lecture in the Yeshivah Ketanah in Grodno. At the age of 22, he headed a group of students who transferred from Grodno to Mir. However, his four years in Grodno with Shkop had a profound influence on his approach to Talmudic analysis.
In 1928, Shkop traveled to the United States in order to raise much needed funds for the Yeshiva. After delivering a lecture at Yeshiva University, he eventually acceded to Rabbi Bernard Revel's invitation to serve as a Rosh Yeshiva of Rabbi Isaac Elchanan Theological Seminary in New York. In his absence from Poland, he was greatly missed by Rabbi Yisrael Meir Kagan and Rabbi Grodzinski, who pleaded with him to return. He also received a scathing letter from Rabbi Yeruchom Levovitz, the mashgiach of Mir, which, according to an eyewitness, he ignored. In 1929, for unknown reasons, Shkop returned to Europe.
Sha'arei Yosher is largely concerned with the intellectual principles by which the law is established, rather than with concrete laws, and is stylistically similar to the Shev Shema'tata of Aryeh Leib HaCohen Heller, on which it was partly based.
Death
As the Russian army was about to enter Grodno during World War II, Shkop ordered his students to flee to Vilna. He himself died two days later, on the 9th of Cheshvan 5700 in Grodno. Shkop is buried in the Jewish cemetery in the Zaniemanski Forshtat section of Grodno.