It is a juxtaposition that almost sums up where the club finds itself exactly 10 years to the week since emerging from administration.
They are ambitious, forward-thinking and involved, through being full members of the influential European Club Association, in conversations likely to change the face of UEFA club competition in the next couple of seasons.
However, harsh financial realities, the kind still biting hard in the straitened world of Scottish football, are never far away.
Motherwell have been forced to borrow money over the past year from their directors as well as The Well Society, a membership scheme set up three years ago with the intention of giving overall control to the fans, to meet funding shortfalls.
Despite countless initiatives, increasing attendances is proving difficult and Stuart McCall, the manager, is already issuing warnings about player budgets being cut again despite his side competing for second place.
With all that in mind, it appears the project established to create that panacea of becoming a wholly supporter-owned organisation must surely be reaching a crossroads.
The Well Society needs to raise £1.5m to acquire a controlling stake in the club after former chairman John Boyle gifted his shareholding to an independent trust. They are understood to be around £1m short.
The society stages its agm in the Millennium Suite at Fir Park next Friday evening and you sense something may have to give before long, whether that involves settling on a smaller shareholding, seeking to bring in fresh investors or giving the green light to find a new buyer.
Dempster, the chief executive, desperately wants to see Boyle's intention of passing the club lock, stock and barrel to the local community fulfilled and continues to bang that drum, but she does not sugarcoat the answers when confronted on how much longer Motherwell can hold on to the dream in the present climate.
"We sent an email to season-ticket holders who hadn't joined The Well Society and then followed that up with telephone calls from a group of people including myself and the players," she recalled. "I think we brought in a commitment of around £40,000 by direct debit in that campaign. We don't hide at this club and I try to answer as many emails to people as I can.
"What I don't want our supporters to take from this interview, though, is that everything in the garden is rosy. Over the last year, we've had to take third party loans, utilise some Well Society money that will be given back and have directors' loans put in as well.
"We are not lying to fans. The last year has been really, really hard."
Dempster was brought into Fir Park by Boyle in 2008, four years after the club had come through its financial meltdown, and has helped to put it on an even keel.
She has no doubts Ann Budge will do precisely the same at Hearts as that club prepares to emerge from administration with a supporters' organisation, better-subscribed than the Motherwell counterpart, in line to take full control down the line.
Dempster welcomes the idea of those without a footballing background entering the game and believes Budge will face no problems whatsoever in entering an industry in which women remain underrepresented.
"Ann is a very experienced businesswoman and she is not going in there with her eyes closed," said Dempster. "The idea football now is still the domain of tracksuited men and people in grey suits isn't true. I see football as full of opportunities for people that haven't been involved in the game because they bring new skills and ask different questions. It has made real progress."
Her next big idea, influenced by the trouble she has encountered in bringing new faces through the door at Fir Park, is to see a proper study performed into whether the costs of watching football need to be addressed. "It has never been done," said Dempster, whose background lies in advertising and media.
"You keep hearing football is too expensive. Is it? Our team is performing well and I don't have an answer on why we had only 3800 people paying in at home to Kilmarnock recently."
For all the challenges at home, though, Motherwell enjoy an enviable and rarely-publicised position at the heart of European football. Dempster attended the annual meeting of the ECA in Barcelona last month and is excited by discussions currently taking place with UEFA over altering the format of the Europa League.
"The first time I was involved in an ECA conference was in Doha a couple of years ago," said Dempster. "I got into the lift and found myself standing beside Rummenigge and van der Sar. It felt like some kind of paralell reality. We are now full members as a club and I am on the communications and marketing committee. There are some early talks about a different set-up in the Europa League from 2015-16, and it is great to be part of that.
"One idea is to have regional mini-leagues that could secure two home games, for example, and that would be interesting for us."