Spamalot?  You might if you’re using the wrong words in your email marketing.

Years ago, the role of the email inbox gatekeeper was one that pivoted on the propensity of email to actually be spam and do away with that message before either the ISP had to process it or the recipient fell prey to the cloaked message.  As time passed, receivers became wiser to the game spammers played and created more robust checks including whether messages had been marked as spam, network lists containing known origin information about bad senders (blacklists) and measures of email engagement as of most recently.  But, one of the bulwarks that has made it through to this day is the checking of spammy words when email content is analyzed.  It is still a critical piece of email deliverability that everyone should be aware of but can be easily dismissed for more sophisticated checks.  If I had a dime for every time a legitimate sender had mistakenly created a cacophony of spammy sounding words simply by selecting those which were not alarming by themselves but when added to others made the message appear as spam, I wouldn’t have to order off the kid’s menu anymore.  This usually is followed up by a discussion on how to avoid being dinged next time around.  You won’t find many major email receiving networks weighting word choice heavily (although it’s still built into the pre-delivery check at most), but as you start to send into the long tail of smaller domains, you can find yourself really being tripped up as spam checkers have become virtually free and easy to use, and most importantly, are still effective in ferreting out bad mail.  So, how do you avoid your messages becoming false positives that get relegated to the spam folder?

Hopefully the following tips will help you find a way with your email marketing to do just that.

Your ESP
Most ESPs these days have a built in content check you should take advantage of.  I’ve seen some that are seamlessly built in to campaign creation workflow whereas others require a few extra button pushes before seeing results.  But, however your ESP has these tools implemented, you should take advantage of them.  It’s what you pay them for and a clean creative is imperative to good deliverability.  Usually you can get some assistance in interpresting the results from the experts on staff as well.

Deliverability vendors
Some ESPs outsource message checking to 3^rd party deliverability services altogether.  Or, if your ESP isn’t integrated with one of these vendors, you can sign up for your own account to get a better read on the type of content you’re sending out.  Be proactive, though.  Willful ignorance will most likely cost you.  Companies like Return Path and Pivotal Veracity have tools which will review your content and tell you if there are any red flags.  Of course, there are a slew of other smaller companies which offer this type of service at a discount as well.  One of the most advantageous aspects of doing a check in an automated fashion with one of these services is the report you’ll get which then can be distributed around to the different teams responsible for the email creation process so the results are easily seen and shared.

Spam Assassin
By far, this is the most popular (and free) application available to email receivers that scans and assigns a numerical score to each word found that’s on the “bad” list.  There are a ton of other rules in place that Spam Assassin checks for as well, but word usage plays a prominent role in labeling your email as spam.  The more words you have that are on Spam Assassin’s list, the higher your score.  Depending on the threshold set by mailbox administrators, your mail will be quarantined, bulked or outright blocked.  This is also the engine that most content checking tools use for their basis of determination of the nature of the creative – will an ISP see this as spam?  For a complete list of rules that Spam Assassin checks for (including those around word usage), check the latest listings at the Spam Assassin website here.

Receivers
Sometimes you’ll come across ISPs or email rendering applications that will post rules around what they define as spam.  For example, Road Runner uses a special bounce code for messages coming in that triggers their anti-spam filters based on content.  If you send enough email out that has spam words in it (i.e., a large campaign going to enough volume at a single ISP), you run the risk of all your mail leaving that IP address being blocked.  Microsoft has also provided a healthy list of words and patterns to avoid in the content so recipients behind Outlook are protected.  Here’s a list of words extrapolated from spam resources as well.

Free self service tools
If you want something lightweight you can use on your own without being plugged into an ESP or a deliverability vendor, you can download MailingCheck and install to your desktop.  From my experience using it, you get a decent overview of what, if any, content triggers exist.  It will provide the actual listings but you’ll have to do the leg work and research what exactly the impact of a certain word or combination of words is.

When you find words designated as spam in your content, you should first decide if the language is enough to cause harm to your email marketing deliverability.  Just because I use the word “free” in an email marketing promotion won’t get me blocked, but it will most likely show up in some content checkers.  However, using the word 30 times and with accompanying words like “hot” and “young” (think of a back to school campaign) anywhere in the content will most likely shunt the mail permanently to the spam folder.  If you must use a word, use it sparingly.  Also, try using words that describe the same intent but do not show up on the spam hit list.  Test repeatedly to find the right mix of verbiage to convey your message without offending the spam checkers, which are computer driven and don’t get the subtleties of written language as easily as we do (read Bayesian filtering if you’re up for the more technical details).

Takeaway: Spam checkers use content analysis of words to determine whether a message is legitimate or not.  While the content may look benign to the human eye, a machine scanning your message may disagree and inadvertantly mark your message as spam due to the perceived toxic combination of words used.

It’s hunting season, folks!  Not “wabbits” this time of year, but rather companies in the email space.

Over the last few weeks since 2010 began, there have been several notable mergers and acquisitions taking place.

1. SubscriberMail acquired by Harland Clarke Corp. (Announcement)
2. Pivotal Veracity acquired by Unica (Announcement)
3. Japanese company A-Care Systems acquired by Experian to merge with CheetahMail (Announcement)
4. Zimbra acquired from Yahoo! by VMware (Announcement)

What is going on out there?  Some folks are still cleaning up the mess left after their New Year’s Eve Party and February is still a few weeks out.  Yet, the business decision makers for these companies have been hard at work to launch these new ventures after the ball dropped in Times Square.

The following two theories come to mind:

• Email is not dead.  There has been a lot of talk over the past few months after a controversial article was posted in the WSJ about how email has had its run, other social networking technologies have steamrolled over it and that the mode of communication is outdated beyond its prime.  If that were the case, why would companies be scrambling to pay out for their rivals or complimentary partners to help make their service offering more robust?  I would imagine that if email were dead, people would be fleeing from the email marketing community in droves, which is not the case.  Yes, AOL announced depressing news of lay offs as it realigns itself with an advertising and content model.  But, this is an outlier in the email marketing equation as the company attempts to hold onto to capitol and keep from further hemorrhaging money.  Not indicative of the whole industry.
• The economy is improving.  And the companies investing in these ventures believe that wholeheartedly.  We’ve heard it from the government, seen it by the pickup in sales this past holiday season over Q409, and can appreciate it with the slew of jobs being added to email marketing companies that just didn’t exist while the depression was in place.  My own company, Bronto, is hiring now more than I’ve seen in the last year or so.  Why?  Because the management team believes that investment in expanded talent will help scale and match the demands of the economy as it rights itself.  These investors acquiring other companies feel the same way.

Some have said that the dip in valuations of companies coming off the economic depression in the US has led to the deals and eventual acquisitions of the companies.  Others say the motivation for the bought companies to reduce costs and drive revenue by getting an infusion of cash is what spurred the move.

I am not a financial expert, but I spoke with industry colleague Michael Perham about the topic to get a better idea of why this is happening.  He used to run Business Development at AdKnowledge and is familiar with this space.  He mentions that balance sheets look really good right now in a soft economy (let’s face it, 2009 wasn’t good for many folks) and that companies are looking for a way to diversify their revenue streams to have a wider suite of offerings in their space.  Expanding one’s position in their vertical is key right now to not only take out the competition but also better dictate your own pricing structure.  Less competition equals greater control over price points.

Also, it’s important to note that M&A (merger and acquisition) activity significantly slowed down or stopped in some industries during the slump in the economy so it could be argued that companies are just now able and trying to get in on the deals still available before the prices rise again thus increasing valuations.  We might be seeing what is the beginning of a major run on companies in the email industry.  Similar to what Responsys did back in Q309 when acquiring Smith-Harmon, companies are getting more creative and aggressive as they realize that dollars are being scooped up with more marketing opportunities discovered, but just as a natural resource, the amount of wealth to be tapped into is finite.  You can’t magically double or triple your recipient base and cause more conversions because you will it so.  But, what you can do is ensure you have complimentary services to the core services you offer and as much of an all in one solution for your customers.  Granted, this mainly applies to companies that are being pushed to chase the dollar from VC backed boards or equity firms – their number one goal for business is to make money off their investments.  Wall Street finds roll-ups like this attractive when a company has gone IPO and thus becomes a reigning factor in making business decisions.

Do you have any other M&A activity you’d like to share?  What are your thoughts?  Do you think we’ll be looking at a significantly reduced number of players come next year this time?  I’d love to get your opinion on this.

Chris Wheeler
Director of Deliverability at Bronto
@ChrisAWheeler

Takeaway: If eMail marketing is dead, how come so much smart money is being invested into it?

Originally posted at the Email Experience Blog (EEC) here and at the Bronto blog here.

The internet was designed to be a free exchange of information wherein anyone, upon a loose framework mainly having to do with networking and rendering capabilities, could join, share and digest what they wanted. Email was developed as a predecessor to the internet.  Again, one in which, as long as you had the most basic SMTP compliancy between networks, messages would be handed off between point A to B.

Today, email has turned into a monumentally powerful marketing tool and communication channel that still rivals the internet and other upcoming social networks, regardless of which side of the “email is dying” debate you fall under. With email marketing, forward to a friend, sharing links, email filters and forwarders, along with major ISPs providing outsourcing solutions (like Google Apps), the audit trail of an email is sometimes all but impossible to decipher without CSI level forensic header analysis.

But, you don’t care about all this.

What should you care about?

When you place an order to have something delivered with the USPS, UPS or FedEx, that item almost never leaves that company’s chain of custody.  Meaning, if you dropped it off with FedEx, the recipient will most likely receive it with FedEx.  Again, there are exceptions, but the vast majority of the time this is the rule.  When you send an email out, though, it may be going to a Yahoo! domain address, then forwarded on to a Gmail domain address and finally rendered in Outlook 2007.  What can you do to ensure that your mail has the highest rate of making it to its final destination regardless of the cyber hops in the middle?

1. Ask your recipient up front if their email address is still, indeed, the right one to be using. I check over 8 different email accounts on a normal day, and with inbox email aggregators with dynamic collection addresses (such as OtherInbox), I probably have several hundred email addresses (with OtherInBox I can use disposable email addresses) that will get to me somehow.  However, the email address to sign up with your service when I was a fresh college grad and using my Alumni account may no longer be at the top of my list.  So, I appreciate it when companies I do business with ask me if that’s still the one I should have on my account.  If it is, I click through on a prompt when I login.  If not, it takes 2 seconds to change.  I don’t get asked this every time I login, but perhaps, every 6 months or so to ensure the email address is fresh.  Guess what?  My Alumni account is forwarded to my Yahoo! account.  So, I changed it to have my Yahoo! account receive the email directly (and thus avoid any errant filtering on the part of my school).

2. Authenticate outbound email. Period. DKIM was designed not to break when making multiple hops in an email’s path to the final destination.  Unfortunately SPF will because of the technical nature of email headers, but with DKIM enabled mail, if it comes through at Gmail verified and then is forwarded on to AOL, the DKIM signature stays intact and the message has a higher likelihood of being delivered.

3. Here’s the bad part.  Just like you as a sender pushing mail out to a recipient, when email is forwarded to another domain by the recipient domain, the reputation and deliverability of that mail falls back on the ISP doing the forwarding.  For instance, I run my own domain hosted through Gmail.  When you send an email there, it gets forwarded to Yahoo! which is what I consider my central email nervous system.  But, sometimes, email from Gmail gets bulked at Yahoo! because of Gmail’s reputation.  This means I don’t get my mail.  What can you do about it?  Gently remind your subscribers to check their spam folders for mail that may have accidentally fallen prey to a filter somewhere.  In my case, I’ll get email that randomly gets bulked (as opposed to breaking any obvious best sending practices) and have made it a habit to check my spam folder often.

4. Check your content in multiple web clients. Oftentimes, an email sent to a Comcast domain looks fantastic, but when forwarded to an AOL accounts, looks horrible.  Now, like in #3, a lot of this is out of your control if the actual content is changed en route by the ISP.  But, if you ensure that your content looks good in the different clients, you increase your chances that when an ISP doesn’t reach in and play with the HTML when it’s being forwarded along, it will look fine in the end email inbox.

5. Have unique identifiers or parameters in your unsubscribe links tying an email address back to a particular sender. This way, your email software will understand the “fingerprint” in the unsubscribe link and know for which address an unsubscribe was logged, regardless of which email account the unsubscribe click actually comes from.  For instance, if I unsubscribe from my Yahoo! address on an email that was sent to me originally at a Gmail account but was forwarded on, you could end up shooting yourself in the proverbial foot.  I could have any wanted email to my Yahoo! account stop but the Gmail email continue.  Recipients will oftentimes setup multiple email addresses for one account (such as Amazon.com allowing you to have different customer accounts based on the unique email address and password combination – your significant and you could both use thesmiths@smiths.com but have different passwords to your own accounts), or across multiple accounts you as an ESP or single sender support (wherein I may shop at 3 different stores your ESP hosts email for), so directly tying that recipient’s unsubscribed email address to their preferences (and not the one that happened to actually do the unsubscribing) is key.

This is pretty technical stuff, folks.  But, in order to stay on top of the original intent of email being free flowing and having as few barriers as possible, you must be cognizant of the challenges in your path.  Reach out to your technical team to ensure you’ve got these points covered.  And remember, an email address is easily disposable.  We, as marketers, tend to see them as having high stickiness.  But, recipients can come and go with fluidity and tracking them along the way with their permission (ultimately their keeping you informed of their moves) keeps you in touch with your customers.

Chris Wheeler
Director of Deliverability
Bronto Software
@ChrisAWheeler

Takeaway: Sending an eMail is like dressing your child up to go out on a cold winter day. Make sure you’ve buttoned it up right so that it arrives in much the same condition it went out as.

As originally posted on the Bronto Blog…

By now, most email marketers have probably come to understand that sending email is not without risk.  As with any marketing, knowing your audience and serving up something that will entice them to convert is key.  Two methods email recipients have to let you, as a marketer, know they don’t like what you’ve sent them is by either unsubscribing or lodging a complaint with their ISP (largest still is Yahoo! with 106MM unique US inboxes according to the latest report).

Note, these are not representative of recipients (your potential or existing customers) telling you they don’t care or are indifferent to what you’ve sent them.  But, rather, they’ve gone out of their way to deliberately tell someone they don’t appreciate the email (either you, directly via the unsubscribe or the ISP via a complaint).

Let’s dive into the complaints a bit more, though.  These little bits of data a recipient fires off to their ISP or 3rd party service (like SpamCop) have two effects:

1. It signifies to the ISP that a subscriber of theirs has identified what she considers to be spam.  When these are added up over time and the recipient base, that ISP domain can begin blocking the sender.
2. It is compiled in the email platform you’re using and usually, like with Bronto’s Sender Rating, can impact your ability to send email out.  Also, that recipient is unsubscribed from future mailings until they re-optin.

At its core, a spam complaint is a person raising their hand and saying “Yuck.”

How do you measure complaints? Based on the above effects, there’s real money being left on the table after every complaint is lodged.  It not only affects the LTV (define) but also shows the value of your program as determined by the aggregate of the recipients’ reactions.

Start Simple. If you don’t yet have a way to assign a monetary value to a complaint, take it slow.  Look at your marketing spreadsheets or your data warehouse (or wherever you keep the incremental value listed per customer/prospect, even if it’s on a legal pad somewhere) and ask yourself “How much will it cost me when one person tells me they don’t want any more email?”  Is it $10?  $5?  If you have really high incremental revenue per item, it may be more.  If you’re about providing a more informational email, it will be much lower.  But at some point, you need to define how many net dollars will come out of your budget each time a new recipient tells you “No!”

Stay consistent. Once you’ve got the value down, be sure to apply it to all recipients across the board fairly.  You can break down the values per mailing segment, but in my experience, it’s more effective to have the opportunity cost assigned multilaterally.  Makes it much easier to compare one campaign to the next within your campaign.

Be true to yourself. The whole point of email marketing in the first place is to spread the word about your company, service or product, right?  Pay attention to complaints coming in (of which any good email platform should expose) and act on this information.  Turning a blind eye or accepting the complaints as collateral damage for emailing will result in potentially alienating your recipients.  And, with that individual, you’ll lose their willingness in the future to even get your email.

Don’t be afraid of complaints; embrace them.  The spam complaint isn’t going anywhere soon.  Many ISPs still use it at as the glue tying senders to email performance, recipients are being trained more and more to just “spam it” from their own web or thick clients, and successful marketers know exactly how much a complaint drives out of their potential success in dollars.  Take action when receiving them and use your marketing savvy to avoid more in the future.

I’ll leave you with this thought…

39% of all respondents said they used the “report spam” button often or very often. – MarketingSherpa “Email Marketing Benchmark Guide 2008″

Takeaway: Take action when receiving complaints and use your marketing savvy to avoid more in the future.