The weather had finally turned, and he was on a spring recruiting trip when an old friend pointed out something he’d already discovered on his own.
“This was at a big high school combine with 50 different schools there,” recalled Montgomery. “A coach from the SEC who I’ve known for a long time told me, ‘I’ve been on the phone trying to get transfers for two months. I’ve neglected our players.’
“He said, ‘Shane, I envy you. You might have the best job of anybody here.’ ”
The personable Montgomery had to look no further back than the most recent stop in his 36-year college coaching career to appreciate why the SEC coach said what he did.
A former record-setting quarterback at North Carolina State, Montgomery arrived in Hanover after one year as offensive coordinator and then interim head coach at Massachusetts in 2024, the 10th stop in his career.
“I had gotten there in late February, and we had taken like 30 transfers at the beginning of the semester,” he said of his time in Amherst. “It was a revolving door – it’s like that throughout the FBS and a lot of the FCS – and you do not have many kids who are going to stay with you for four years.
“It’s tough to develop a culture when you have kids that only come in for one year and then transfer because of NIL or money. The great thing at Dartmouth is kids come here because they love the school. The mindset of our players is they are here to get one of the best educations in the country and play good football.”
Long before all the roster turnover, NIL, and football at the FBS level led him to appreciate what he found at Dartmouth, Montgomery was a high school quarterback on his way to making the game his life's work.
At Newark Catholic High School in Ohio he quarterbacked the Green Wave to a 13-0 record in 1984 before moving on to North Carolina State. A three-year starters with the Wolfpack, he earned offensive MVP at the 1988 Peach Bowl and the ’89 Copper Bowl. Voted a team captain as a senior, he graduated as the NCAA record-holder for passes in a game after hoisting up 73 in a loss to Duke.
After being chosen to the All-ACC second team in his final year, he gave the World League of American football a shot with the Raleigh–Durham Skyhawks before heading back to NC State for two years as a graduate assistant.
Those years on the bottom rung of the coaching ladder tested whether this was the career path he wanted to follow.
“When I was 'GA'ing at NC State, I wasn’t making much money, so I’d do anything,” he said. “I would get up at 4 in the morning, drive to Durham, and had basically a paper route where I would drop off the Wall Street Journal, the New York Times, and maybe the Greensboro paper to businesses and newspaper racks, where I had to put a certain number in and remove yesterday’s.
“I did that for almost two years. I’d get back to my house at seven, sleep for an hour, go to class, and then to the (football) office. I still wonder how I did it.”
But he stuck with it and eventually went on to land his first full-time position as quarterback coach at Chattanooga in 1993. He stayed with the Mocs until moving back to his home state to serve as offensive coordinator and quarterbacks coach at Miami in 2001.
Selected as a finalist for the Frank Broyles Award as college football's top assistant coach in 2003 (when his QB was a fellow named Ben Roethlisberger), he was promoted to head coach a couple of years later.
It was while coaching the RedHawks that he had his first real introduction to Dartmouth.
“Dave Shula’s son Chris played for me at Miami,” he said, “and talking with (Dave) through the years I got to know a little about Dartmouth. Not the ends and outs, but I knew it was a great school and they were having a lot of success on the field.”
Let go as head coach by Miami after the 2008 season, Montgomery would go on to put in one season at Akron, five at Youngstown, one at Charlotte, two under Curt Cignetti at James Madison, two at Buffalo, one at East Carolina and then the one at UMass.
With his five most recent stops at the FBS level, it was only natural that the Ivy League’s 10-game schedule and late start to the season had him wondering if Dartmouth would be a good fit when he first looked into coming to Hanover.
“Getting the chance to meet Sammy McCorkle and some of the coaches was really eye-opening,” he said. “It helped me see what type of program this is. But coming in I still didn’t really know what kind of talent we would have.
"I saw early on that, hey, we’ve got a lot of really good players. You can see that with all the (grad transfers) we send out, mostly to the FBS. I was in the Southern Conference, and at Youngstown, we played North Dakota State and South Dakota State, so I knew how good the players can be and what kind of competition there is at this level. Going through a year in the Ivy League, I now know it’s just like any other league. There are really good players who are going to go on to play at other places after they graduate and have the chance to go to the pros.”
His first year at Dartmouth gave Montgomery the opportunity to really appreciate the talent level in the Ivy League, and take in the lay of the land around the conference. He's learned that while players may come in with more impressive high school GPA's than at some colleges, a passing grade on the field requires the same things wherever you are.
“It doesn’t matter what level you are at, and it doesn’t matter who you are playing,” he said. “Wins and losses come down to a handful of things, and number one for us offensively is turnovers. Two of the three games we lost last year, we had crucial turnovers for different reasons. So the first thing we’ve got to continue to address this year is taking care of the football.”
Charged with that responsibility under Montgomery again this fall is quarterback Grayson Saunier, a second-team All-Ivy League pick a year ago.
“He’s fully healthy, and I expect to see a lot of improvement in him this year,” Montgomery said. “We really like him and feel pretty good about the skill players we brought back. And it’s been exciting watching some of the young guys get their first chance to start or provide depth.
“That’s one of the things about Dartmouth," he continued. "Look at last year with Max Wentz, who played center as a senior after never really playing before. He goes out and makes all-league, and now he has a chance to start at Ball State. That’s the story of a place like Dartmouth. Guys develop, and they stay for four years.”
And with a full year now behind him in Hanover, Montgomery understands why.