CRM on the Mac

We’re all salesman” is one famous adage of the successful. That’s why it’s imperative that you always maintain your contacts in perfect order. While we love our MacBooks and iOS gear, we’ve often wondered why CRM is so challenging on the Mac platform.

A large part of the blame lies with Apple itself. While Apple continues to innovate in many areas, it’s clearly not devoting sufficient resources to the MacOS platform and that clearly shows from its lackluster, but free, contact management tool, Contacts.

The good news is that things are getting better, but that’s largely due to a major technology trend that has a growing number of applications moving to the cloud. That’s why we moved away from iCloud syncing and switched to Google Contacts.

The reason for that change was predicated by our history with corrupted contacts due to syncing errors between our local Mac address book and iCloud. Errors that twice lead to the loss of all categorization of about 2,500 contacts, a dreadful débâcle.

Restoring Contacts required importing a backup of vCards, which sacrifices all contact categorization, a feature Apple calls “Groups.”

For those of you who would like to follow in our footsteps, we have created a sidebar below, which details the step-by-step process of moving away iCloud and using Google Sync instead:

How to Change from iCloud Contacts to Google Contacts

Whatever you end up doing, it’s always good to make a regular backup of your Contacts file by choosing File/Export/Contacts Archive… from the menu and exporting all your contacts to a backup file. Do this before beginning this process.

Here’s our successful step-by-step procedure, which, by the way, also works great for moving from Mavericks to Yosemite, as noted below:

  • Access the “Application Support” folder in your user folder (hereafter referred to as “~/Application Support”) by holding down Option key while choosing “Go” from the Finder menu and opening up your “Library” folder. Backup the “AddressBook” folder, preferably to an external drive.
  • If you’re just upgrading to Yosemite and would like to bring over your Contacts from your previous OS, copy the backup AddressBook folder to ~/Application Support. Open Contacts and your previous address book will show up flawlessly in Yosemite (we tested this on 10/24/14). 🙂
  • We tried several times to sync Contacts with Google Contacts to no avail. Nothing happened and there’s a lot of online fingerpointing as to the real culprit, but suffice it to say that there’s no love lost between Apple and Google. We were, however, very happy with an app we purchased a year ago, called Contacts Sync For Google Gmail ($3), which works very nicely indeed.
  • Use another app, called Export Address Book ($5), to export all your Mac contacts using its “Gmail Contacts CSV” format.
  • Access your Google Contacts account online and click on the “More…” button, choose “Import…” and select the file you just exported above.
  • Once you have exported/imported your contacts and have Contacts Sync For Google Gmail installed, disable any Mac-based Google syncing by choosing Mail’s” “Accounts” menu and deselecting any Google “Gmail” syncing of “Contacts.”
  • Because our previous Contacts file was synced using an iCloud email account, we used another email account to set up Google Sync. If you’re using your existing iCloud account make sure to back up your Contacts file first and delete all contacts in your online iCloud account by logging in and selecting all contacts and hitting the delete button.
  • Once you’re ready to sync with Google Contacts, enable your iCloud account in “System Preferences” and select Contacts, Reminders, Keychain and Find My Mac, which are the only items we’re syncing via iCloud (we’re also syncing Calendar with Google Calendar).
  • You can now open the Contacts with Contacts Sync For Google Gmail app from the Finder menu bar and choose Sync Now/Gmail Contacts -> iCloud in Contacts.” Our results showed “2,731 records created.”

  • You now will by synchronizing your Mac Contacts with Google Contacts. Because we were suspicious of the efficacy of this system, we chose not to automatically sync Google Contacts with Mac Contacts, preferring instead to manually sync and monitor the results, for reasons explained later in this article.

    However, Contacts Sync For Google Gmail works splendidly and we don’t seem to have any any problems related to its use specifically, yet the process could obviously be far simpler, and it should be.

Another impetus precipitating this change was the greater array of third-party CRM applications that use Google Contacts as the synchronization basis for their services.

That Apple is falling behind in this area is another critical shortcoming in the company’s advancement of the MacOS platform. It really does make you long for the Apple evangelism days of the 80s and 90s.

So how do we manage our CRM system on the Mac? In a massively kludgy fashion.

Day-to-day: Cobook

We use a free app, called Cobook, to manage the “front-end” to our Mac Contacts/Google Contacts system. Cobook was recently acquired by Denver, Colo.-based FullContact and has actually become more difficult to use over time, a sign of our over-engineered times.

Yet Cobook provides the fastest interface to Apple’s Contacts because its top menu bar icon is easily accessible from any application, and it manages to add a number of highly desirable features to Contacts that Apple has yet to engineer itself.

While we now live in a highly social world, one major area where Contact falls down on the jobs is connecting your contacts to their social networks. Yes, it can be hacked with custom fields but Cobook manages all this seamlessly by live syncing Contacts with Facebook, LinkedIn and Twitter.

Another area where Cobook shines is the ability to “tag” contacts, which is the modern world’s way of categorizing contacts. Tags are infinite, as they should be, and can quickly be entered when adding new contacts, so it’s easy to add “supplier,” “friend” and “bowling” to a contact and find it quickly using either tag.

Contact Updating: FullContact

We have come back full circle to FullContact, which is now in beta but appears to work most of the time. What FullContact does is sync with your Google Contacts account and use its web crawling services to update your contacts with social media profile pictures, gender, and any other data the company can lay its hands on, for just $10 per month.

But it also has its work cut out. That contact record we uses to illustrate this story, of the dearly departed Steven P. Jobs, was continuously updated by FullContact with Steve Shapiro’s information, who is a Mac columnist but besides first name has absolutely no other resemblance to Steve Jobs.

FullContacts even substituted Shapiro’s picture for the photo we used for Steve Jobs, which we had to edit prior to taking the screenshot pictured above.

As always, proceed with caution. While we like what FullContact is doing, obviously with help from Kaspars Dancis, the founder of Cobook, it still has a lot of work to do to make their interface easier to use. Another demerit, it won’t find “Steve Jobs,” only “Steven Jobs.”

FullContact Card ReaderFullContact offers an iPhone app, called Card Reader, that you use to take photos of your business cards, which are then manually transcribed in a few hours.

CRM: Base

We have tried them all, Brewster, Contactually, Daylight, Elements CRM, Relationship,, Stride, Triggerfox, Xobni Smartr, Zoho CRM, even the latest 5pm offering, 8am, but none of them have the seamless architecture we have come to expect from state-of-the-art SaaS applications like Asana, Mint or Slack, or even groundbreaking desktop software like Keynote, Mailbox, Numbers, Pixelmator, Reeder or Sketch.

But one SaaS (Software as a Service or cloud) application does get very close, Base ($15/mo.) from Palo Alto, Calif.-based FutureSimple Inc.

BaseBase CRM is well-designed and offers a versatile import system, a fast way to clip contacts from Facebook and LinkedIn, plus highly graphic reporting.

Base’s interface is very well thought out. It also offers native IMAP e-mail integration, so you can send directly from inside Base, versatile import mechanisms, including Mac Contacts(!), syncing with Google Contacts, plus elegant reporting, including full-screen charts.

But Base’s best feature may well be a Chrome Extension, called the Base Contact Clipper that lets you add any Facebook or LinkedIn member to your Base CRM list right away. Very convenient, although you would wish that Base would introduce one for Safari too.

Periodic use: Contacts

Apple’s contacts manager is capable enough to keep most users happy, so few developers have accepted the challenge of building a truly useful Mac database manager. Yet, as most users will acknowledge, Contacts is one of the weakest elements of Apple’s ecosystem, one that leaves a lot to be desired.

While things have gotten slightly better with Yosemite, including further simplification of the interface, one major Contacts irritation remains. When Contacts merges duplicates, it simply combines records and puts conflicting data in the Notes field.

That may be fine for casual users but it’s a major headache to peruse 2,700 contacts to see which ones were merged and what the Notes field reveals was the duplicated information.

Apple, here’s a bonehead simple solution: After de-duping, please create a Smart Group that contains merged records, that way users can review merged records easily.

Business Card Scanning

Once again we’ve gone through the wringer for you and emerged very wrinkled. Ever since the slow death of CardScan, thanks to its useless purchase by DYMO (part of Newell Rubbermaid), we’ve lamented not having a solid Mac solution for scanning business cards.

Yes, there’s such a thing as the NeatReceipts desktop scanner, but for $341, we’ll pass. And reviews suggest its software is not great either.

And, as we pointed out more than a year ago, LinkedIn acquired CardMunch to essentially kill it. Now we know why LinkedIn never updated the CardMunch app from December 2011 on, in May the company announced a business card integration partnership with Evernote to scan contacts.

Of course, this requires that you buy the significantly overpriced Fujitsu ScanSnap Evernote Edition, which, at $495, should literally suck business cards out of your briefcase, scan them and stack them neatly on your desk afterwards. 😀

Fuggedaboudid, Evernote. After several dalliances with CamCard and ScanBizCards, the two highest rated business-card scanning apps in the iTunes Store, we went back to FullContact Card Reader.

While ScanBizCards and its Asian ilk scan “meishi,” Japanese term for business cards, nicely, they all want money to “store” your cards. One offering from Japan, called Sansan, does not even add scanned info to Contacts.

If we’re going to pay for a service, it better be nicely designed and easy to use, which is why we recommend FullContact Card Reader. Like CardMunch, the service uses an offshore company to manually input scanned cards for maximum accuracy.

FullContact Card Reader will scan your cards and will get them mostly right, as our tests show. The app offers a host of features, including integration with and Sugar CRM. FullContact charges nothing for the first 10 cards, and then $10 flat for 50 cards, $90 flat for 500 cards or $100 for a 1,000-card annual subscription.

In our ongoing quest to find a great Mac contact management and CRM solution, we have tried many tools, all listed below, to help you achieve the high quality contact management you deserve.

To best understand how you can build an effective Mac CRM system, you need to know the strengths of each application used to manage aspects of list creation and maintenance, so here goes…

Clean Text ($20)

Quite often when transferring files from databases to programs like Panorama Sheets or Direct Mail, you will discover that your export file contains non-ASCII text characters, such as foreign accents, em- or en-dashes, that some programs or services will choke on. Clean Text quickly removes these. It works well enough, although it has yet to be optimized for Retina displays, so the text does not appear “clean,” esthetically speaking.

Cobook (free)

As mentioned before, Kaspars Dancis’ Cobook is a godsend for Mac users. Cobook simplifies rapid data entry and searches, rendering the use of Contacts almost unnecessary. Cobook simplifies address entry with smart fields that can detect what type of data you’re entering and automatically enter it into the right fields. This doesn’t always work, of course, but it’s a big plus.

Another great Cobook feature is the easy way it allows you to integrate social media contacts into Contacts, although, of late, its Facebook connection appears broken.

CobookCobook shines in the contact editing department, offering users the ability to group edit contacts, like assigning or removing tags, indicated with a “#” (pound or hashtag).

However, you should be careful here. When starting to use Cobook and connecting to social media accounts, you may accidentally activate the program’s ability to import all your LinkedIn contacts. Result: Your Contacts file grows instantly.

The added contacts could be helpful for future business opportunities. That’s why tagging contacts is very important. Cobook simplifies that process. Unlike Contacts, Cobook actually displays group names, appropriately called “tags” by Cobook, in each record. You can easily add or remove tags to quickly organize contacts. And Cobook can do this for single or multiple contacts at once.

Contacts (free)

Mac users need Contacts because Apple Mail and a large number of other programs seamlessly sync with it, allowing you to instantly call up names for easy emailing and also to store contact names on iCloud for syncing with an iPhone or iPad.

By right-clicking an email address in Mac Mail, you can quickly add a contact to Contacts. Apart from this nifty integration, Contacts is not really suitable for fast entry and keeping data clean. For example, whenever you use the “Add to Contacts” email address feature, Contacts will label the newly added email address “Other,” which presents numerous challenges in sharing contacts with other applications.

Another irritation: While Contacts allows you to categorize contacts by group, and a single contact can belong to multiple groups, you have to hold down the Option key to see what groups a contact belongs to. There is no view that display all tags, a better way to describe groups, at once.

Direct Mail (free)

Once you have all your email addresses organized, you need some way to connect with them on a regular basis. You can download Direct Mail, a free app, to email contact lists. Direct Mail lets you import email templates created by other programs or designers and rapidly create ad-hoc lists or import existing lists for promotions.

“DirectDirect Mail is an easy-to-use promotional tool that lets you send emails to small or large lists and features its own built-in address list manager.

When emailing, you have two options. If the number of emails you’re sending is less than 50 per month, Direct Mail is free.

To send more, you need to sign up for the company’s e3 Delivery Service built directly into Direct Mail, with monthly sliding scale charges, or you can buy 5,000 credits for $60. These pre-paid credits are a better deal for CRM users who don’t email frequently.

eMail Extractor v3 ($20)

eMail Extractor does something unique: It can extract emails from text files. In the “Doing CRM the Mac Way” process described later you will see how to use this utility to create highly targeted lists of prospects you have been too busy to add to your Contacts.

eMail Verifier v3 ($30)

The problem with collecting contacts over a long period of time is that people move around, so many email addresses become outdated, resulting in bounce rates as high as 20% on a typical promotion.

Email marketing services that charge by the number of emails you send love this of course. The more email addresses you have, the more they can charge you. eMail Verifier will test each email address in your list by pinging them without actually sending anything, and verify if they’re still valid or not.

Export Address Book ($4.99; App Store)

Export Address Book is a must-have utility that deals with a very annoying shortcoming of Contacts: it only allows contact exports by group if you choose the vCard format, which includes a lot of redundant data.

“ExportExport Address Book is literally a lifesaver if you use Contacts and want to export contacts by category in the most popular format accepted by all applications, .CSV, or only include certain fields in your export file.

What if you want to let your suppliers know that you have a new accounts payable manager who will see to it that they never get paid? 😉 Export Address Book handles that task beautifully.

MailChimp (free for less than 2,000 email addresses)

MailChimp is one of the most popular email services in the business today and is headed up by the affable Ben Chestnut out of Atlanta. A former graphic designer for Cox Communications, Ben has turned MailChimp into one of the most full-featured direct email platforms in the business, as well as featuring a tongue-in-cheek sense of humor that simply must be experienced.

Most importantly, MailChimp created one of the first APIs that lets third parties access your email lists directly. This comes in handy when you use CRM apps like Base to sync with it.

MailSteward ($50)

Wish you could archive excess email in an outside archive? With 100,000 emails in Mac Mail and an additional 70,000 stored separately, we hear you. MailSteward allows you to export your email inbox folders to a standalone database archive that can be searched quickly using multiple parameters.

In “Doing CRM the Mac Way” below, we’ll describe how we use MailSteward to resurrect old business development contacts for promotional mailings.

Numbers ($20; App Store; Free with new Mac)

You often need a spreadsheet to look at files that have been exported by other programs. Apple’s popular spreadsheet Numbers handle this task beautifully. Numbers lets you examine exported data in a table format to help you clean up contact lists.

One popular use of Numbers is to join two fields. Some event invitation sites require that you paste a combined first and last name field plus email address to build your invite list. In Numbers you can combine First Name and Last Name fields using this simple trick:

  • Start with a sheet that has first names in column A and last names in column B
  • Create a new column C and paste in the formula C=A&” “&B.
  • Replicate the formula down for as many contacts as you have.
  • Copy the joined column C, select Column D and choose “Paste Values” from the Edit menu.
  • Now you have a list of joined first and last names, and you can delete columns A, B and C.

Panorama Sheets ($50)

James Rea still runs one of the oldest Mac development companies, ProVUE, publisher of Panorama Sheets, which lets you handle list manipulations in memory quickly. Panorama Sheets can split database record fields or join them in the blink of an eye.

This is a boon for those of us who need to deal with bonehead organizationally challenged co-workers who store names in a spreadsheet using one field for both First and Last. Panorama lets mend the error of their ways with ease.

WhiteList (App Store; $8)

It may seem obvious but nothing else does what WhiteList does: Search though your Mac email inboxes to find people you emailed most, ranked by number of emails sent.

In the following section, “Doing CRM, the Mac Way,” we show how to use WhiteList to create a list of your most important business development contacts so you can personally reach out to them.

Doing CRM the Mac Way

We’re going to describe a process that every business executive faces. You have emailed hundreds of business prospects over the past few years but you were too busy to add many of them to your Contacts each time you engaged one another.

Now your business development email folder is full of hundreds of emails of people you want to reach out to with an update about your firm or to send them “We just got funded” emails. How do you accomplish this?

The good news is that it can be done. The bad news: it takes many steps to get it right. Here’s the process flow, using the tools mentioned above:


Store all your contacts in Mac Contacts, since everything, including your iPhone and iPad, depends on this contact list. You will want to add new contacts directly using that handy right click (or with “Control key” if you don’t have a trackpad or two-button mouse). Make sure you categorize your contact’s email correctly because most CRM programs will want to import your contact’s work email. Also make sure you add each contact to the right group so you can select custom lists.

Don’t know how to organize your Contacts by category? Here are a few basic categories or “groups,” as Apple calls them, to help you get organized:

  • Promo – This is your core business promotion group. All people who are to receive your promotional emails should be on this list, save perhaps for your personal contacts and suppliers. You should definitely create this group and use whatever name you prefer.
  • Personal – Put your family members, doctors, and other personal contacts here, so you can avoid sending them unwanted business promotions. Some may be interested, like that dentist who wants to invest in your business, so you can always add them to the Promo group too. Contacts lets you assign contacts to multiple groups, a powerful feature (and the good news is that Google Contacts will keep them organized that way).
  • Entertainment – You know visitors are going to ask you for personal restaurant recommendations, so keep this group separate from your personal contacts. This list also makes it easier to suggest a place for a business lunch.
  • Suppliers – Keep your suppliers and vendors separate, so you’re capable of sending emails, like “We’ve moved!”

The sky is the limit when it comes to organizing contacts, particularly when you use Cobook to “tag” contacts. You might also want to split family from the personal group, so you can keep their GFs or BFs separate from their better halves. 😀 You get the picture. But don’t overdo it. Part of being well-organized is keeping things simple.

Add and Update with Cobook

We encourage you to use Cobook to maintain your contact list and avoid using Contacts as much as possible, saving you time.

Parse Inboxes with White List

You do have a “Business Development” folder, right? If not, make one pronto and use it to store emails of people you want to do business with now and in the future. Use White List to ply through this folder, or other relevant folders, in Mac Mail and filter a list of people you emailed most. Set a cut off of two emails and consider everyone above that as a candidate for your promotional, or promo, list.

Distill Email Addresses with MailSteward

Next, export Mail’s Business Development folder and import that inbox database into MailSteward. MailSteward will then create a list of all email addresses found in your business development folder.

Use Bioinformatics to Compare Lists

You can compare the list of email addresses generated by MailSteward with the one you created with White List to find the people you corresponded with most. A great list comparison tool is Bioinformatics’ Compare Two Lists. This nifty tool will show you the difference between two lists, their intersection (what they have in common), etc.

Isn’t it amazing that all this functionality is not offered by a single application? Who wouldn’t love to see a Mac utility developed that would be able to do this based not only on a single field but to compare complete Contacts databases, so you can find out what people are missing from what list.

Test Email Addresses with eMail Verifier

Once you’ve extracted email addresses from a MailSteward database or exported them from Contacts, you can test the validity of email addresses using eMail Verifier, and save only the ones found to be still correct.

Send Targeted Promotions with MailChimp

Export your final list to MailChimp or the Direct Mail app, where you can create or add them to your “Promo” list. MailChimp also synchronizes with Base and Nimble, the CRM apps described below, so use a “promo” tag to identify the correct list to sync with.

Using a (SaaS) CRM Service: Base

One way to manage outbound communication is to use online services that fundamentally mimic Why not itself? Because, as most salespeople will tell you, is difficult to use.

If you like what CRM services can do for you, we recommend you look into Base. Base debuted in 2011 and shines in ease of use. It also integrates with your e-mail and lets you communicate directly with prospects. Another CRM service, Nimble, currently supports direct messaging with Facebook, LinkedIn and Twitter.

The Starter version of Base costs $15. If you opt to pay $125/month you can get a few more features, notably an integrated telephone number.

Turning Your Gmail into a CRM System: Contactually

Contactually helps close sales by reminding you each morning, or at any interval setting specified by you, to follow up. You can also specify “Actions” by contact, which can provide greater granularity for tasks required for each business account.

Contactually also turns categorizing contacts into a game by allowing you to virtually “toss” contacts into “buckets,” much like a videogame, turning drudgery into entertainment. Best of all, Contactually also integrates with both Gmail and IMAP email accounts for a better communication experience.

As you can see there are numerous challenges in maintaining contacts and accomplishing CRM on the Mac. It’s our sincere hope that a few smart Mac developers will read this story and be inspired to create a truly awesome solution. Meanwhile, please share this article on Facebook or retweet it if you find it helpful.


Michael Tchong

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Michael is a professional people watcher and the founder of four ahead-of-the-wave startups. He’s also a top-rated innovation and trends speaker, plus an adjunct professor of innovation at the University of San Francisco and UC Berkeley.