Some parts of this itinerary will work fine, others not. Two questions, is your boss walking alone and how old is he? The times you've quoted appear to be the "Official" times, which are set by experienced hikers who are just trying to cover the distance. New comers to this activity will have a hard time keeping to this schedule, especially if they stop to smell the roses (or Blue Gentians)
Day 1 - That would be fine. One variation would be to take the historic cable car (Cable car in the San Francisco sense of the word - a small train pulled by a cable) that runs up to the Reichenbach falls and walk from there. It involves more walking, but the scenery is spectacular. There is a hiking path, but I choose to walk on the road, otherwise I spend all my time watching my feet instead of the scenery. Seeing as this is day 1, the long uphill section from Roserlaui to Grosse Scheidegg may be a bit of a test. You can pick up the Post Bus for the long run down to Grindelwald.
Day 2 - Looks good, although the walk from Alpiglen to Kleine Scheidegg is all up hill. For that section you can take either the old hiking trail which roughly follows the railway line, or the newer Eiger Trail. Both will get you to KS.
Day 3 - The hike from Mürren over the Sefinenfurgge pass is a bit strenuous. There is a long scree slope to be climbed and from memory the path isn't well marked on the other side. That may have changed.
Day 4 - This is the part I think may be too much. This is a proper alpine route that needs some experience and shouldn't be attempted alone. It's long and very strenuous. If this section must be done, I would suggest breaking the trip by staying overnight in the Blumlisalphutte at the top of the pass. It's a proper Alpine Hut, and all SAC Hut rules apply.
Day 5 - There is a cable car that runs between Kandersteg and Allmenalp, not a chairlift. Beyond that, I can't comment as I haven't been there yet.
As I've been writing this, I've been thinking that your original itinerary might be overly ambitious for a beginner hiker. The Oberland is spectacular, but with spectacular scenery comes challenging hiking. A shorter walk would be a lot easier, reduce the risk of spained ankles, pulled muscles or blisters, and be a lot more enjoyable. Being able to slow down and appreciate your surroundings is more important than clocking up "Frequent-Hiker Miles"
This would be my alternative hike.
Day 1 - Take it easy. From Meiringen, take the Cable Train to Reichenbach, check out the falls, then walk to Rosenlaui and stay overnight at the Hotel Rosenlaui (I've always wanted to stay here) http://rosenlaui.ch/en/Angebot/Welcome There is a spectacular Glacier Gorge nearby that is well worth a visit.
Day 2 - Rosenlaui to Grindelwald. You can catch the Post Bus if you want.
Day 3 - Stay an extra day in Grindelwald, go to First and walk back, or climb the steps that go up to the Oberer Gletscher. Lots of things to do in Grindelwald.
Day 4 - Grindelwald to Wengen. An early start needed. Don't do want I did and wait til after lunch. I only got as far as Alpiglen and had to stay there for the night. It was fun though. You can catch the Gondola to Männlichen and walk down from there as a plan B.
Day 5 - Wengen to Mürren. Different possibilities here. Either walk down from Wengen to Lauterbrunnen, then take the cog rail to Grütschalp, then walk to Mürren, or take the train to Lauterbrunnen and use the extra time to visit the Trumellbach Falls before going to Mürren.
Day6 - Mürren to Griessalp via Sefinenfurgge. A proper Alpine Pass, well above the tree line.
Day 7 - From Griessalp, take the bus to Reichenbach im Kandertal (a different Reichenbach), then take the train to Kandersteg. Visit Oeschinensee after lunch.
This is a virtual tour I put together that covers most of the walk. It is actually for a walk from Meiringen to Interlaken, but the first half is the same.
This walk covers some of the most spectacular scenery in the world and your boss won't be missing out on anything for it being shorter, apart for a few blisters.
Hope this helps