From what is written on the reverse, I believe this is the high school graduation photograph of Chester Ingalls Conn, Class of 1906 at Woburn, Massachusetts High School.
From online research, hopefully correct: [corrections welcome]
Chester Ingalls Conn was born 24 May 1890 at Woburn, Massachusetts, the son of Horace Nichols Conn and Marion I. (Smith) Conn.
His paternal grandparents were George Henry Conn and Mary E. (Nichols) Conn. His maternal grandparents were Rufus and Susan A. (Ingalls) Smith.
Chester graduated from Tufts University and at some point after 1910 and before 1920, moved to Portland, Oregon. He's mentioned in a 1916 Tufts catalog as being principal at a school in Hobart, Washington. Perhaps his stint at Washington allowed him to meet Winogene Jane Jones, whom he married at Pierce, Washington in 1914.
Winogene Jane (Jones) Conn was born about 1888 in North Dakota, the daughter of John Foulkes Jones and Mary Jane (Williams) Jones. Her family subsequently moved to Washington state.
The 1920 Census found Chester and Winogene at Portland, Oregon, with two children and Chester's sister Ethel living in the household. Chester was working as an accountant. He had apparently found his calling, as he was still working as an accountant in the 1930 and 1940 Censuses of Portland, Oregon.
Chester died in 1954.
If you have corrections or additions to the information above, please leave a comment or contact me directly. Thanks!