If John Alexander had only achieved one milestone in his multi-decade career – signing Alanis Morissette, and facilitating her watershed Jagged Little Pill album – it would have been more than enough to cement his position in rock music industry history.

John Alexander, Aerosmith

John Alexander (bottom) with Steven Tyler and Joe Perry of Aerosmith (left).

But throughout a long, storied career – one that has encompassed artistry, management, record companies, publishing, performance rights, and now a very strong suit in consultancy – Alexander’s vision has resulted in some other exemplary accomplishments, thanks to his acute business acumen.

“I always negotiated good and fair deals, club dates, tours, record deals, and/or publishing deals for my artists,” says Alexander, who began his professional career in the mid-1970s as John Pulkkinen, lead singer of Octavian, a seven-piece Ottawa pop band known for such hits as “Good Feelin’ (To Know)” and “Round and Round.” They released one album, Simple Kinda People.

“I was a teacher at the time in Ottawa,” Alexander recalls. “When we got the deal, I told my parents, much to their dismay, ‘I’m going to quit teaching and join a rock band.’ They didn’t like that too much, until they heard me on the radio one day, and said, ‘That’s cool.’”

Octavian toured coast-to-coast, but eventually went their separate ways in 1979. Alexander joined bassist Terry McKeown to form Alexander/McKeown Management, representing Warner recording artists David Roberts and the Teddy Boys, as well as Montréal singer-songwriter Luba, and Toronto rockers Sheriff, the latter two signed to Capitol. It was under Alexander’s tenure that Sheriff recorded “When I’m With You,” the song that would, extraordinarily, top the Billboard Hot 100 in 1989 – four years after the band broke up.

“We sent Jagged Little Pill to every major record company in America and Canada, including MCA. Everybody passed.”

John Alexander, Alanis, Ringo

John Alexander with Alanis and Ringo.

But his greatest moment was yet to come. Invited by MCA Records to head up the Canadian label’s A&R division, Alexander received a demo tape from a young Ottawa artist looking for her first break into the record business. “I got a tape from Alanis when she was 10 years old – a song called ‘Fate Stay with Me,’” Alexander recalls. “I loved her voice, but I was so new in A&R, I figured that if I signed a 10-year-old girl from my hometown, I may not be in A&R that long. It took four more years before I was re-introduced to her.”

That re-introduction came from local musician Leslie Howe, who sent Alexander a demo of his band One To One, piquing enough interest for the A&R man to visit Howe’s Ottawa studio to hear more. While there, Howe asked Alexander if he had a minute to listen to something from a young artist he was working with at the time.

“He played me a video he did in Paris with Alanis Morissette, and I was so intrigued by what he showed me that I flew back to Toronto. I didn’t sign One To One.” Instead, he signed Alanis. But Howe did produce both dance-pop Alanis albums issued by MCA Canada – her self-titled debut and Now Is The Time­ – selling more than a total of 200,000 copies here, and earning her a JUNO Award for Most Promising Vocalist.

Despite her success, Morissette’s MCA option wasn’t renewed, and Alexander says the songwriter told him that she didn’t think she’d have a career singing other people’s lyrics, but wanted to sing her own. By then the New York-based Senior VP of East Coast Publishing for MCA Music Publishing, Alexander agreed, and stuck by her despite her un-renewed publishing option. Alexander asked his friend, professional songwriter Glen Ballard, to meet with her. Ballard was a producer at Quincy Jones Productions, who’d worked on the Michael Jackson classics Thriller and Bad. He had also co-written the MJ hit “Man In The Mirror,” the No. 1 Jack Wagner single “All I Need,” and the Wilson Phillips chart-topper “Hold On.”

“It became a fortuitous contribution,” Alexander understates. The duo co-wrote the sea-changing Jagged Little Pill, which has sold more than 33 million copies around the world, won seven Grammy Awards, and established Morissette as an international superstar. It was spearheaded by the caustic “You Oughta Know,” an angry feminist anthem that inspired a trend of similar singers,from Meredith Brooks to Tracy Bonham.

“Glen Ballard did the album on spec,” Alexander recalls. “I didn’t pay him – he just took [percentage] points [of the sales].” In hindsight, what amused Alexander was the initial lack of response to Pill by everyone to whom he submitted it. “Once the album was made – I had hired Alanis a manager named Scott Welch – he and I sent it to every major record company in America and Canada, including MCA. Everybody passed,” he says. Lawyer Ken Hertz finally convinced Madonna’s Maverick Records co-founder Freddy DeMann and A&R head Guy Oseary to hear the record. Morissette was signed immediately. “After hearing the album at Glen’s house, Freddy turned to me and said, ‘John, I think you’ve discovered the female Bob Dylan for our generation,’” Alexander recalls.

John Alexander, Avril Lavigne

John Alexander with Avril Lavigne

For Morissette’s publishing deal, Alexander recalls a moment where he was questioned – just as the writing for Jagged Little Pill was underway – whether the company should renew its option. Alexander was adamant. “When you’re in this business, and you’re in the position of believing or not believing in artists, you have to stick up for what you believe in,” he says. “And I’m proud that I said, ‘Just do it,’” says Alexander, who also negotiated to eliminate the right-of-refusal clause that cleared Morissette’s path to Maverick.

His record-company and music-publishing days behind him, the former senior VP of Membership with ASCAP has moved on to consulting, recently brokering some Yangaroo agreements with NARAS (the National Academy Recording Arts & Sciences, home of the Grammy Awards), the Academy of Country Music, and Montréal-based digital media and entertainment company HITLAB.

He’s also hoping that lightning will strike twice with Boulevard, a Vancouver-based rock band that Alexander originally signed to MCA Canada in 1988. Boulevard split, then re-united in 2015, and released a new album called Luminescence in 2017 that’s received European acclaim.

His future looks bright, but even in his past, Alexander has influenced generations through his decisions. As he humbly states, “I’ve contributed to the Canadian music scene.”