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Office 365: A conversion in more ways than one

Posted 5 years ago in Tech by Andrew Jessett
Posted by Andrew Jessett

Our implementation of Office 365 also marks my conversion from cloud computing sceptic to evangelist. Ironically it was the day after my Xero one year anniversary that we moved to Office 365.

I came from a traditional server and infrastructure background and didn’t know much about cloud computing when I started at Xero (other than that syncing your photos via Picasa was really handy). I distinctly remember looking at our outsourced 3rd party mail system and thinking “we need to bring that in-house and manage the servers ourselves like you are supposed to.”

But as my first few weeks of Xero life rolled by I started to realise how cool and powerful cloud computing is and how well it fits Xero’s own use. I couldn’t believe it, but in a few short months I found myself fully endorsing a move to a cloud based email system and I couldn’t wait!

Xero internal IT working the weekend for the email migration

After the decision was made, Office 365 soon became the logical conclusion for us. It’s one of Microsoft’s more exciting products and it’s still running that familiar exchange platform that many of us know and love. It solves a lot of problems, especially in terms of infrastructure.

We have a global presence with several offices around the world. To replicate what we get with Office 365 globally, utilizing a traditional in-house server model, would mean standing up quite a bit of infrastructure, adding a lot of complexity to our environment, and requiring much more support staff. Office 365 didn’t just give us email too; we get Lync which is a great tool and a pretty decent upgrade to the currently used Skype, and of course SharePoint online. Microsoft seems committed to the platform, introducing all sorts of cool features next year. And all this comes with a 99.9% uptime. A lot of our core applications are also Microsoft based (Office, Yammer etc), so choosing a product that integrates with these was extremely important.

Unfortunately my enthusiasm dampened when I looked at the task at hand. Most existing mail servers are either connected to a company’s Active Directory (a centralised source of usernames, passwords and company data that is used when you “log in” to a computer) or not connected to Active Directory (products like gmail etc). We had a system that was connected to the ugly stepsister of Xero’s own Active Directory. It was hosted in a fake Active Directory “bubble”, where all user names and data closely matched our own Active Directory. Although that might sound like it would make things easier, it actually made things a lot more difficult. Conversely our Active Directory was an empty shell. Usernames were in there, but that’s about it. The introduction of Office 365 would also introduce Active Directory as the single source of truth for all our applications – this meant we had to collate and import a lot of data. For the first time (from a Xero point of view) all this information was in one place.

The first step was to get an export of data from our current solution. This included user information, distribution groups, mailbox rights etc. This data then needed to be “massaged” so that it could be imported into our own Active Directory – a tough and laborious task which involved other internal groups such as HR to ensure the data was correct. We also had to factor in the addition of extra information from other sources (mainly other contact details such as cell phone number, office address etc), which were included on our intranet but not in the “other” version of our Active Directory. After much pain and suffering the data was eventually imported into our Active Directory. But we were still several months away from actual cutover – this initiated a period of keeping both our Active Directory and hosted email system up to date. Each change in one system had to be replicated in the other, a tricky task given the rate of change at a company like Xero.

It sounds crazy now but we then had to solve one of the biggest technical challenges of the transition – email signatures. Yes email signatures. With the old email system a product called exclaimer was used to stamp a person’s email signature to outgoing messages. The signature was constructed as it left our system based on their details contained in the “fake” version of Active Directory our hosted email platform utilised. This solution caused us many issues and a lot of support time spent correcting them, especially around the look and feel (any design change precipitated many weeks of difficulty trying to get the format correct).

A centralised client based solution would be ideal. However, with our mixed OSX and Windows environment this proved very difficult. We researched many products but none were suitable, as the OSX platform did not support any of them. In the end we decided a web based solution would be the way forward (cloud based systems to the rescue!) – this would also need to be tied to our Active Directory to keep that single source of truth permeating through. Disappointingly we couldn’t find anything off the shelf that could do this, so we ended up having to employ a 3rd party to develop our own bespoke web application. It seemed a lot of effort just to get a person’s email signature in place! But we achieved we set out to do, a consistently branded email signature that we could easily update and change in the future.

Once done it was then onto the migration itself. Thankfully we never got into the habit of using .pst files at Xero so all mail data was stored in a particular person’s mailbox. This meant for some hefty mailbox sizes (a select few pushing over the 10GB mark – large by corporate standards). We also faced the same issue whereby we could not migrate from an existing exchange implementation, so the transfer of data was problematic. Luckily for us a product called migrationwiz came to our rescue and we set down the long road of our initial migration of data.

Before we knew it we were only a week away from cutover and still had not obtained our licences from Microsoft. The whole system was still running on trial licences. We also discovered that the approach to the migration was potentially wrong and that we would need to actually migrate our data after we had cut across, not before as we had planned. This was due to the fact we would likely cause several double-ups of email messages when we attempted to do the final sync of email. It was also about this time I started to panic a little.

However we pulled ourselves together and focused on the task at hand. The data migration approach was adjusted and the licensing (after several “high level” discussions with Microsoft) arrived a day before the cutover. We were go for launch!

The weekend of the cutover itself was in some ways a straightforward affair. However, the team pulled some long hours both days to make sure we were ready. Because our iPhone users have their contacts in Exchange we then turned to another cloud based product, Airwatch, to centrally reset everyone’s email profiles. On the iPhone suddenly SMS messages weren’t showing who they were from, just numbers, which would have freaked a few users out. We fired off a parallel contact sync and contacts were all quickly restored across the company in minutes. Another massive benefit of having things in cloud and cloud enabled devices.

Monday hit and the preparation we had done served us well. Personally I felt that the power of Yammer as a communication medium really shined through as we were able to help people in real time in multiple locations. As our other offices came online, the team worked through the night ensuring everyone was able to get their email.

And here we are, enjoying the fruits of our labours and utilizing the Office 365 platform. It went well and although there were a few bumps along the way there was minimal disruption to the general Xero workforce. For me it was a bit of an early Christmas present to get the company onto such a cool and exciting platform, as well as to finally see the realization of so much hard work come to fruition. It’s also a good feeling knowing that Office 365 is really just a first step in many improvements to our internal infrastructure – bring on 2013!



January 7, 2013 at 5.48 pm

Thank you for sharing your journey and being totally upfront about the bumps on the way

We are looking at moving to Office365 over next few months so this really helps
p.s Would love to learn more about your Email Signiature Tool looks handy

January 7, 2013 at 6.11 pm

Thanks for the read Andrew. Sounds like fun with your mixed AD environment. Feeling the same pain with moving to 365 when using Exclaimer.
Q. Does the app you’ve developed just generate the signature files and put them on the local PCs?

Adrian Pearson
January 8, 2013 at 1.15 am

What next guys – a move from Rackspace to Azure?

January 8, 2013 at 11.39 am

Looks like great project to achieve. As a matter of interest, what is your round trip time / latency to MS365 from NZ and does this cause any issues with hosted Lync?

Andrew Jessett
January 8, 2013 at 3.02 pm

@Anna – Glad we could provide some insight! The tool was developed by a local software company specifically for this project (so wasn’t off the shelf). Users basically browse to an internal website, log in via their Active Directory credentials and then the signature is copied to their clipboard once the click a button. The application of the signature is all done manually by the user.

@Dan – Glad you enjoyed it. Above should answer your question. Ideally we would have used a centralised tool that automated signature deployment (“eMailSignature” seemed okay for instance), but given our mixed environment of OSX and Windows we simply couldn’t find a product that would work for both.

@Adrian – The Xero application servers are hosted at Rackspace but our internal back office systems are hosted by a different 3rd party. We aren’t planning any changes in that space.

@Greg – Thank you! Our O365 instance is actually hosted in the US as we registered using our US office. There is no difference in performance from our previous hosted solution. Lync is really snappy as well. I had used an internal OCS solution in my previous role and I can’t tell the difference between that and our new O365 provided solution.

January 8, 2013 at 3.58 pm

Congratulations on a job well done. I will also be involved this year in a 365 rollout. I’ve never been a fan of ‘reinventing the wheel’ so thank you for sharing your experience and providing the heads up in some areas. We are really looking forward to using 365 as well.

January 14, 2013 at 3.45 pm

Fascinating read, thanks for sharing your experience. There’s some great lessons in there, which we’ll take on board as we investigate this direction also.


Andrew Davis
January 25, 2013 at 2.07 pm

Hi Andrew

Thanks for the interesting post.

Is there anywhere I can find out more about why Xero has chosen Office 365 – both as your internal platform and to partner with?

The reason I ask is, it seems to me that Xero’s philosophy and technology are actually much closer to Google’s – both companies were “born on the web,” both advocate anywhere, anytime, any device access, and both focus heavily on user experience and simplicity.

(Disclosure: I am a Google Apps reseller, and many of my clients are passionate about both Google Apps and Xero.)


Andrew Davis

Rod Drury
January 26, 2013 at 9.24 am

@Andrew, I can take that one

We still do a heap of document production. Board reports, briefs, detailed specifications.

We do use GoogleDocs for a lot of stuff like highly iterative small documents but find that it doesn’t have the same level of control for final document output.

I’m still super frustrated that Office, with all that local processing power on the desktop, is so hard to set up for collaborative working.

So nothing is perfect and we are using all.

Email is a biggie for us. We do a lot of email automation (which I know we could spilt out) but we weren’t comfortable going fully GMail just yet.

We’d love to be fully cloud but I suspect there is a few more years of development before we’d find it compelling.

Moving to Office365 was the next big step. So we’ve moved from a dedicated hosted environment (really a remote FM model) to being fully hosted. So far it’s working OK.

There still needs to be a lot of innovation from Microsoft and Google as both their solutions are far from perfect. Archiving especially drives me nuts. Why don’t Microsoft have a web based email archive solution so we can search over all mail and not have to store things more than a month? I don’t want to think about deleting anything.

We also use Box, SmartSheet, Trello and a bunch of other cloud tools internally.

Hope that answers the question,


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