There are some obvious names to throw out there
Jimmy Adams
The former WI captain has been at Kent for three seasons now...last season they done ok but he's not managed to get them promotion to Division One yet. Right now they stand at mid table having played nine games and promotion this season looks doubtful aswell. He's known to be an intelligent man and actually spent a brief time on Gibson's coaching staff as batting coach for one of the t20 world cups..while also being coach of Jamaica's u19s for a spell. Personally i'm not sure he's ready yet.
Phill Simmons
Simmons was actually in line to take the job when Gibson got it...Phil was gonna be head coach with Gibson his assistent..but due to financial hardships they couldn't afford both so decided to go with Gibson. Phil has done ok thus far with Ireland, got them performing as a good unit and they beat most of the other low rated sides around them. Good experienced coach but i have questions over whether Phil could really inspire these guys to new heights.
Anyway there's one name that has me intrigued and here it is...
Robin Singh
Played International cricket for India and has learned his cricket philosophies over there but he was actually BORN in the Caribbean...Trinidad to be exact where his parents still reside to this day. Now lets look at his record...
Coached the India A-team featuring the likes of Rohit Sharma, Gambir etc
Part of the India senior team staff as fielding coach alongside Gary Kirsten when they were ranked number one
Has coached Mumbai Indians and won the champions league with them
Is current head coach of Barbados Tridents for the up coming CPL
Here is some comments he made about working with Dwayne Smith at the IPL
Link"I worked with him on his batting and technique, of course, but actually we spent more time working on Dwayne's mindset: his temperament, getting his confidence up, sorting out his approach to the game and his self-belief. That's very important for a player, especially batsmen," he says. "The focus was on getting Dwayne to understand specific match situations, how to adapt and how to win matches from them. I didn't have to tinker too much with his batting because it's solid, but yes we did try to work out how to make him a better-rounded player.
Robin Singh says the two hit it off well in the IPL but it was in Bangladesh that he was able to work really closely with Smith. "Today with all the access to video technology, bowlers can figure out where to bowl to you so it is vital that you stay ahead of the game. In Dwayne's case, we worked hard on getting him out of his comfort zone. For example, to play more between mid-off and extra cover because some bowlers saw he was very strong on the legside. Stuff like that, not massive changes. Dwayne's a good listener so that made my job easier".
This guy has ample coaching experience at all levels and has worked with some of the best coaches around...no doubt he will have learned a lot from Gary Kirsten who guided India to number one and then guided South Africa to number one....he's also coached some of the very talented indian batsmen we see around today...and I believe we need a coach who can bring the best out of our young batsmen because that is what we're lacking right now...could you ever see Gibson making those comments above about Smith?
I can only imagine how Singh would advise the likes of Darren Bravo, Kraigg and Blackwood...the core of our batting order for years to come.Another bonus is he's not only a great batting and tactical coach he also doubles up as a very good FIELDING COACH ASWELL...so we'd kill two birds with one stone there.
Of course another option would be Richard Pybus himself who has a glowing record as coach...but there's no way he could be director of cricket AND coach aswell...so i don't see it happening.
Robin Singh would be my pick purely because he's experienced and would bring something new to our cricket interms of the batting.
Bennett is a good guy who has done all he can at domestic level...he also done well with the A-team in India...but is he really gonna teach our players anything new in both the tactical and technical aspects of the game? IMO we need someone who will bring certain skills to the table..which is why i believe Singh is good because he's got a background in working with great coaches and also he's a great batting and fielding coach in his own right. 
why would a " real " Caribbean run behind every and any coach with foreign experience in preference to one with a proven track record of leading Caribbean cricketers to success, over a sustained period of time.
Singh IS CARIBBEAN regardless of whether he represented India or not. I just believe from a batting perspective he'd be able to show our batsmen new things having worked with most of India's legends behind the scenes. Lets remember this man was on the india coaching staff when they had Tendy, Dravid, Laxman, Sehwag etc..so he will have seen how those guys went about things in the nets and on the field and will be able to pass that information on to our young players like Kraigg, Darren and Jermaine. 