McKendry's Junior NCAA season with New Mexico Lobos had caught the eye of several scouts. He was being rated highly and looking MLS ready.
The midfielder loved his time in Albuquerque, but from a solely footballing perspective the time to make the move to the pro ranks with the Caps was now.
"Obviously it's my home city, so I know the club pretty well, and that kind of made the decision a whole lot easier," McKendry told us. "If it was another club or another country it would be kind of a harder decision because I don't know exactly what I'm going in to.
"The big part for me was coach Carl welcoming me back over the years and bringing me back to train and making me feel that I was part of this club, which was huge, so that made it easy."
Robinson wanted to add some more midfield depth, with one eye on the 'Caps new USL PRO team, and after looking at what other options were around in the MLS draft, it became clear to him that McKendry was the man he wanted and he decided to pull the trigger now and offer McKendry a MLS contract.
"I watched a lot of Benny last year and he done very well," Robinson said. "You hear all these reports coming out about him, that's he's a top ten player in the draft, and things like that. Well he was the previous year, I knew he was. I just think the timing was right [now].
"Ben had obviously made it known that he was ready to have a crack at the MLS level, which was always good because you wonder what players sometimes think. Once he made that known, we done our due diligence on the draft and we thought there were some talented midfield players in there, but they weren't better than Ben. I'm not going to produce another stopgap or block another pathway for my homegrown players.
"We made a decision on draft day that we wanted to try and sign Ben to a homegrown contract and it's worked out great for us and great for him. I spoke to his dad and he's very happy. I do have to thank the New Mexico guys for part of his development as they've been crucial in that as well."
The timing was perfect for the Residency alumni, who had been weighing up whether he should make the move to the pro ranks now or finish his degree. It didn't take too much deliberating. He would put his studies on hold and head back to Vancouver with a professional contract.
"You obviously have to bring out the pros and cons of staying at school for another year," McKendry acknowledged. "Maybe entering the draft or coming back to Vancouver after my senior year. I feel comfortable here. Having the coaching staff, the city, my family here, made it a really easily decision. And obviously the USL. They have a USL team, that's huge. So I know I'm going to get minutes, matter level it is."
Having that new USL PRO team, and the opportunities it will afford the Whitecaps burgeoning array of young talent, was a big persuader in McKendry making the decision to leave college early.
"I think that was a huge part of it," McKendry admits. "A lot of college guys go into this environment and struggle because they don't get the minutes they want but are obviously extremely talented players. So the USL team is huge for me but obviously none of us young guys are shooting for USL, we want to keep moving up, but USL is fantastic for the young guys."
With the likes of Matias Laba, Gershon Koffie and Russell Teibert ahead of him in the midfield depth charts on the MLS roster just now, McKendry knows that he will mostly see a lot of minutes with that USL PRO side this season. But situations can change quickly in football. So can form and injuries.
McKendry also knows that he is coming to a club and playing under a manager that likes to give the younger players chances and opportunities in first team action.
"Carl's big on playing young players. For a guy like me that's a bonus and that excites me cos I know I'm going to get the opportunities to play, which is huge.
"There's going to be plenty of opportunities. It's just about taking it. Obviously I've got to train hard every day, at preseason and all those things. It's just going to be about continuing to work, learning from the older guys and you just got to continue to grow."
With the Whitecaps facing over 40 games this season between league and cup action, Robinson knows that he will need to use every inch of his squad depth to keep the team competitive over what will feel like a very long year. Whilst he has brought McKendry in with more of an eye to the USL PRO roster, the fact that he has rewarded the midfielder with a full MLS contract is a statement in itself.
"I think at the start it will be towards USL PRO, but that's not saying he won't get MLS minutes because he's on my MLS roster," Robinson told us. "I said to him that shows what I think of him, what we think of him and it'll be down to him if he takes that opportunity or not. We've got plenty of games next year. It'll be dictated by his performances in preseason and how he does during the season."
McKendry will add some midfield versatility to the 'Caps. He mostly played a central midfield role during his time with the Residency, but featured all over, including the backline. At New Mexico, he played more as a defensive midfielder. A very attack minded one.
Robinson doesn't want to pigeonhole McKendry and likes the options that he adds to his squad.
"With young players I don't like sticking a certain position on them because I don't think they learn to develop the key characteristics of what is needed in other positions. He can play defensive midfield, and he's very good, but he's a box to box midfield player. We need goals from midfield at certain times of the season as well, so if he can add goals to his bow then I think he'll be a great addition for us."
That role suits McKendry down to the ground and he feels at home wherever he plays in the midfield.
"I'm pretty comfortable with both roles really," McKendry told us. "As defensive it depends who you play alongside with. I don't have any problem going forward and making that late run into the box, to pick up a goal here or there. But if you need me to stay back and defend, I embrace that side of the position as well.
"I'm a confident player. I like to get on the ball and have fun."
There's still a lot of debate in soccer circles about the merits of young players, especially Canadian ones, going through the American college system. Whilst some feel it gives players valuable experience and playing time, others feel the nature of the game in NCAA can stunt development instead of progressing it.
McKendry is in no doubt about the benefit going to New Mexico has been to his playing career and would recommend that path to others currently weighing up their options.
"I think a lot of young players have expectations that are a little but unrealistic in terms of wanting to go pro. When kids hear about the college environment and playing college soccer, especially in the States, there's probably some negative connotations towards it.
"For me it was key in my development from that age of 18 to where I am now. It was huge and there's plenty of good programs in the States. You can enjoy yourself, you can get an education. I couldn't say enough good things about at least my experience. I'm sure I've got a lot of good friends as well that would say the same thing."
McKendry becomes the 8th homegrown player on the Whitecaps' current MLS roster. He's also the only one born and raised in Vancouver. Does that put any added pressure on him to perform and succeed?
"I wouldn't say pressure. I don't think there should never be any pressure when you're playing a game you love. But I definitely have a sense of pride playing for Vancouver and being the only guy from Vancouver here."
Settling in won't be an issue. He has his family and friends around him and his previous training spells with the first team means that he's already a well-kent face at training to many of the current squad. And all of those familiar faces make for a smooth transition for McKendry.
"I know a lot of the guys, which makes it more comfortable. Also, Carl and his coaching staff do a great job of making it a welcoming environment, which isn't always the case in a professional environment. I feel comfortable and the guys have welcomed me really well."
That was clear to see at his first training session as a signed pro. It also helped that while the Whitecaps training camp was just getting underway, McKendry has been in full training mode for the past couple of weeks already.
"I just came off two weeks of spring training with New Mexico. In the springtime most college teams do crazy fitness things. Running up sand dunes, crazy workouts and stuff. I felt pretty good out there. It was fun"
We can't wrap up our chat with Ben without throwing out that well worn cliché of the hard work starts now. It's true, it does. And the only way to push yourself into the MLS mix in this competitive environment is to shine often and improve regularly.
It's the key focus for McKendry in this preseason camp and he knows what elements of his game he needs to continue to work on to get himself to that next level.
"You can never be satisfied with where you're at," he told us. "Seeing the older guys on this team who are kind of getting to the end of their career, you see the workrate that they continue to put in and how they take care of their bodies.
"That's key to being a professional, always wanting to get better, continuing to learn, which is nice to be able to know that as a young player and have those guys as an example to see what you need to do to get better and have a long career."