From Rob, who appears to have long experience in the transit business:
I've often wished for a Steve Jobs of transit. Someone with a vision of how it would work if "it just worked", and the dedication to make it so. Most transit is a huge compromise in service design, operating performance and customer communications, and its biggest challenge often is the willingness of its users and fans to overlook those compromises uncritically. We accept too much that we shouldn't.
I've known people I think are like Steve Jobs; maybe not as confident or charismatic, but systems-oriented with a keen awareness of how customers experience is affected by how transit works – and I find they are rarely in charge. We put people in charge who know about management and organizations, not the ones who have a laser focus on how to produce a product that delights the customer, or at worst works as expected without [the customer] thinking too hard about it.
This is not a critique of the organizational and management expertise that transit also needs. Steve Jobs had great managers without whom his work would have been impossible. The real challenge is to form mutually respectful partnerships — and ideally friendships — between great organization managers and creative, strategic thinkers like Jobs. The key to building these winning partnerships is to accept that almost nobody is a really great manager and a really great creative strategist. The two skills can fit together like lock and key, but only if they choose not to be intimidated by each other. You have to have the confidence that your partner, by exercising his skills, isn't diminishing your very different skills. In fact, he's implicitly praising them.
These partnerships happen now and then in city planning, and often in consulting on the planning side. But is your transit agency even looking for them? Some are.