Since taking over the reins as chief executive in 2015, he has seen the theatre go from strength to strength and this year will help it mark its 125th anniversary.
But as well as celebrating the venue's rich past, he is also looking to the future by further expanding its role in the community and encouraging new audiences through the doors.
"The Grand Theatre is a great treasure. I said when I first started this job that the Grand Theatre has a massive heart and it's the heart of the community.
"For 125 years this beautiful building has stood on this site and to think millions of people have been through the doors in that time is extraordinary.
"It's a privilege and a pleasure to be leading an organisation with such a rich history," said Mr Jackson.
A pivotal part of the theatre's plans a new 200-seat performance space which will be created next door to its current home in Lichfield Street.
It has a working name of The Green Room and will involve an investment of between three and four million pounds.
Mr Jackson says it will enable the theatre to work with the likes of the University of Wolverhampton, colleges, schools and community groups as well host performances and music gigs.
The hope is that it will appeal to people who may not already be regular theatregoers and help bring more people into the city centre which will have a positive knock-on effect for other businesses.
"This is major because it's the Grand Theatre's first expansion project ever, to actually expand the footprint will be tremendous.
"We will be able to attract a completely different sector of the community. It could be anything from a wedding reception to a rock gig.
"The mindset is that we will be able to different things and some we can't do at the moment because we don't have the facilities to do it.
"I see this as a great place for local talent in the community to perform. If someone plays the piano, plays the guitar or sings and they've written new work they can come here. It's a very important development for the theatre," explains Mr Jackson.
The theatre is currently awaiting a decision from the city council on a planning application for the development, which will be on the site of a former post office.
Mr Jackson says it's vital that the industry is constantly evolving and opening the door for all sorts of people.
"You can't stand still in this industry - you've always got to have a vision for the future.
"It's so important that creative organisations remain visionary and don't stagnate.
"It's easy to think that because people are buying tickets, coming to the theatre and being entertained that there is nothing else to do. There is so much more we can be doing.
"I wake up some mornings and have a light bulb moment. It's also about providing opportunities for the staff and their development, they are all creative people so let's let them be creative.
"There is a lot to be gained from the Green Room," he added.
The 53-year-old is also on a mission to show that the venue is open to all, whatever their age of background.
"Theatre must be accessible to everybody. It must not be perceived as being exclusive or only for certain parts of the community.
"We have a duty as leaders in culture and arts to make sure that everybody has access to cultural enrichment and if they can't come to us - we will go to them," he said.
One way the theatre is reaching out to the community is through it's pantomime roadshow which visits schools in the Black Country.
Youngsters are given a 30-minute story-telling of the history of pantomime before a short performance to give them a flavour of the full stage production.
"For many children it's their first exposure to live theatre. I went along to one of the schools and watched the kids - their faces and what they get from it was really quite special," says Mr Jackson.
Strengthening links with amateur theatre groups is also vital, he adds.
West Bromwich Operatic Society, Walsall Operatic Society and Bilston Operatic Company will all stage shows at the venue this year.
"Amateur theatre is a very important part of our programme. It allows us to offer our facilities and expertise to amateur group.
"They learn from their experience here and it helps to build our audience because we get an audience that wouldn't normally come to the Grand because they've come to support their family or friends and we tend to retain a lot of them," explains Mr Jackson.
The 2019 season also includes two 'exciting collaborations' for the theatre; in March a production of Macbeth will kick-off a three-year partnership with the National Theatre and in May Birmingham Royal Ballet will make its first visit to Wolverhampton Grand.
To mark the 125th anniversary, there will be a week-long celebration in November, which the theatre hopes to reveal the details of soon.
"We're hoping to announce a week of exciting one-night events and concerts and then we will co-produce our pantomime Dick Whittington in December," says Mr Jackson.
It's been almost four years since he took over the reins of theatre and he says he's pleased with what's been achieved in that time.
After moving to Wolverhampton Grand from Lichfield Garrick, he found he had to hit the ground running and ensure the venue could cover the loss of council funding which was over £300,000 per year.
"One of my first missions was to make the theatre self-funding because I knew we were at risk of losing our public money and we had to react to that quickly," said Mr Jackson.
One way he did this was to focus on the front of house areas and improve the facilities to encourage people to visit the bars.
The £1.1million revamp brought a touch of the razzmatazz of the 1920's, with the glitz, glamour and opulence of the era featuring in the new decor.
"It had a phenomenal impact on people spending money here, people come to the bear earlier to have a drink or stay after a performance. It changed the experience and people spend longer in the building," explains Mr Jackson.
Another change saw the Grand produce its first in-house show for more than four decades in 2017.
By producing its own work the theatre takes a bigger share of the profits and also takes advantage of tax breaks introduced to support producing theatre.
It also enables them to appeal to a wider audience by offering shows that may not be available to watch anywhere else.
The first show was Brassed Off which was followed by the hugely successful Ladies Day last year and another production is currently being planned for February or March 2019
"A lot of productions are national. They come to us in seven or eight lorries and they are unloaded. The show plays for a week or two and then moves on and people have a choice of where they see the show.
"Producing gives our team the chance to be creative and create something special for the people of Wolverhampton and customers of the Grand.
"It's an important part of a theatre's repertoire. Some theatres choose not to do it but I can't bear the thought of not producing our own theatre. It's important to give the staff the chance to do it too," said Mr Jackson.
He is not a stranger to the stage himself and this job represents his life in theatre coming full circle.
When he was 12 he performed with West Bromwich Operatic Society in a production of The Music Man at the venue in May 1978.
"I remember vividly standing on the stage in awe of the beautiful auditorium and I knew this was what I wanted to do. The Grand was 100 per cent the reason for my move into theatre so I have the Grand to thank for my career and I'm sure there are hundreds of actors who will say the same thing," explained Mr Jackson.
He is also a respected instrumentalist and a conductor and he graced the Grand stage in 2016 when conducted the City Concert Orchestra at the theatre's Gala Night in 2016.
The musician remained tight-lipped on whether he might return to the stage in the future saying he was concentrating on his role of chief executive.
"I feel very privileged to have this position. Show business and the world of theatre is not a job, it's a way of life.
"To have an influence over what people experience in their lives and the cultural enrichment they experience and the changes that that can bring to people's lives is a privilege.
"I don't think there has every been a day I've not wanted to come to work, I sleep, eat and breathe it," said Mr Jackson.
He full-heartedly believes the Grand Theatre has a bright future ahead.
"The vision for the future and the work we're trying to do to expand and develop will help to secure the theatre's future.
"This grand old lady has been sitting on this site for 125 years and I'm sure that in another 125 years somebody will be sitting here saying how amazing it is that she's been on this site 250 years," added Mr Jackson.