As of this week, following an interim spell as head of digital comms at the PM’s Office and Cabinet Office, Simon is firmly in charge of an area that by the government's own admission "is developing in silos and not in the mainstream".
Not that he has any illusions, warning of increasing danger that the government will be left behind by the rest of society's growing digital capability.
Though Simon is by all accounts a pragmatist and unifier when it comes to handling people, he is not afraid to speak his mind.
His old boss Nick Jones, now at Visa, describes him as someone who "can get past all the hot air and challenge received wisdom".
So far, this drive has not been stifled, as evidenced by Simon's contribution to the first ever Twitter-led ministerial reshuffle last year.
But so far he has mainly worked in an environment which understands the need to embrace the fast-moving world of digital.
As the Government attempts to modernise it is now time for him to look beyond Number 10 and the Cabinet Office and fight for online engagement throughout Whitehall.
"People are terribly risk averse"
Simon is keenly aware there needs to be a profound cultural change in communication.
"There’s a fear within government and people are terribly risk averse when it comes to using social media. There’s a culture of the anonymous civil servant, but they should have the ability to get out there and have conversations with the public if appropriate."
Such involvement probably comes easy to him, with his experience as a graduate trainee for ITN, reporting for radio on events like the Oscars.
He got involved in digital in 2000, taking responsibility for launching the interactive part of ITN’s news website.
Since then his CV has included everything from developing the BBC’s red button service through to expanding the Central Office of Information’s data.gov offer beyond the realm of data geeks.
Now the stakes are higher amid this week's launch of government comms reforms, in which spreading good practice from digital beacons like the Department for Business, Innovation and Skills was listed as a key priority.
Reporting into executive director of government comms Alex Aiken and leading a team of ten, Simon will have to rely on persuasion rather than force to bring about the culture change.
The civil service is not known for embracing reform and openness is not always compatible with politics, though the relationship between Simon and David Cameron's director of comms Craig Oliver is supposed to be a good one.
"When it comes to comms, at particular times in the electoral cycle risk and reputation are the guiding factors," observes digital specialist Max St John, the Nixon McInnes MD who was brought in to help with the digital review.
"Social media is often viewed through this lens as a reputational risk. There needs to be a refocusing of the conversation to highlight not just the risks of doing this but the risks of not doing it," he adds.
For "particular times", read the next two years, with ministers increasingly nervous about gaffes by their political underlings, let alone newly vocal mandarins.
It just as well that Jones says Simon’s digital vision is backed by something firmer.
"It is one thing having great ideas but another to make them happen. He can do both."