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Category: Email

There are 5 posts published under Email.

Beyond Email: The Case for the Ideal Business Messaging App

Email sucks. However, as much as people hate it, it is still effective. It is a decades old medium that serves a very simple purpose. Sending a message to another person anywhere, anytime, and on any subject.


They can read it, respond to it, copy someone else in, or forward the entire conversation; it’s flexible, simple and ubiquitous.”


Email works, but just barely. It still has a horrible, outdated user experience often cluttered and littered with spam. What’s especially confusing about emails, are threaded conversations. Oftentimes it will club together emails based on the same subject, even if they were sent to separate people, and threaded conversations tend to be too cluttered. A chain of all previous emails which replete with to, from, and lengthy signatures all in a nested layout, which is incredibly difficult to follow and not visually appealing in the least.


While other technologies have advanced and feel current and contemporary, email’s user interface design is still decades old. It is used by many to communicate professionally, manage tasks, chat, and organize thoughts. However email’s main use case, the ability to communicate and share content professionally is predominantly still the main use. And while other apps have come up to let people communicate (i.e. Whatsapp, BBM) or manage tasks and organize thoughts (i.e. Asana, Trello) there still seems to be a major hole in letting people communicate and share files in a professional work setting via an app that is sleek, modern, and intuitive.


Mailbox created an app that tried to redesign the user experience of sorting, filtering, and dealing with email. I say try, because it was snapped up and acquired before it had a chance to breathe. Mailbox was able to tap into mass excitement over a new experience for emailthat other apps are trying to capture. Several high profile enterprise- messaging apps just raised massive investment rounds; TigerText and CoTap both are trying to offer companies an alternative to email. However, the experience on these apps is just like most other non-enterprise chatting apps. While social networks like Yammer and Chatter — tools that add another layer of complexity over email, to team chatting apps like Campfire and Hipchat — all provide a decent enough way to stay connected and quickly chat.


For example using any one of these many new IM apps like Kato, Slack, or Hall, I’d have a chat room called Marketing, in which I’d have a persistent, infinite chat log about everything marketing related. How annoyingly difficult it would be to search for a decision we reached about our new brand name. Decisions and actionable messages get lost in a constant stream of chatter, often irrelevant to the topic being discussed. Although these apps can enhance their search capability, it just isn’t organized in a way to instantly chat with your team over a topic and reach a decision or take action. So when my designer wants to send me a message about a new design he’s come up with its often more intuitive to send an email because it has that all important subject line, while adding a new topic into a persistent chat room almost feels like it will get lost and drowned out.


However when you look at the rise of messaging apps its clearly evident that there are a number of key features that would be incredibly appealing to business users. The read receipts to let you know when your message has been read or heard, voice messages that add a human touch to your business chatter, quick file sharing, in-stream photo and video messaging capability, and best of all, instant action and reaction from team members.


It is about time that someone comes up with app that lets us move beyond email. We deserve better.


The Ins and Outs of Trigger Campaigns

What’s the first thing you do after placing an online shopping order?


Most of us hop into our personal email as quickly as possible and wait for the ever satisfying “Thank You for Your Order” email to pop up. This email lets shoppers know that their payments were received and the order is processing - your shoes are on their way!


Even though online shopping is a B2C interaction, the same idea applies to the B2B world. In B2B marketing these autoresponders are referred to as trigger emails. A trigger email is an email, or series of emails, sent to an individual based on the activation of some form of “trigger.” The send date or time is relative to the action or relative to a previous trigger email.


The action may come from a variety of places - maybe on your website or from a previous email campaign. Once the recipient has completed (or in some cases, failed to complete) the desired action, they will be “dropped” in a trigger campaign and begin receiving timed emails. These desired actions may be:



  • Whitepaper download
  • Demo request
  • Opt-in request
  • Event registration
  • Survey completion


Used wisely, these interactions allow you to better track your customer and prospect activity to shorten sales cycles and maintain an open dialogue.


Characteristics of Trigger Email Campaigns:


  • They’re specific to a recurring need or objective: Trigger emails are ideal for communicating in response to regularly recurring actions (sign-ups, downloads, etc.)
  • Delivery and message are both automated: The key to successful trigger-based campaigns is automating the triggered message.
  • Emails can be personalized: Often, your trigger email audience is a single recipient because triggered messages are only sent to individuals who have taken a specific action or inaction on your website or previous email
  • Activated by explicit behavior: When an email is triggered by someone completing a specific action, such as downloading a document.
  • Activated by implicit behavior: This uses lead scoring or behavioral targeting to trigger an email, or emails, when someone completes a set of predefined steps or achieves a predetermined score.


Although trigger emails are based on a “set it and forget it” mentality, don’t totally forget about them! Make sure to review and update your message monthly.


In a B2B environment, triggers are low volume with very high open rates. These emails are used to reinforce your company brand and continually emphasize consistent messages and calls to action. Jupiter Research (in “The ROI of Email Relevance”) found that behaviorally-targeted trigger email campaigns get 30% higher open and click-through rates and three times the conversion rate of broadcast email. Some report open rates as much as 70% higher than broadcast email.


Before you pull the “trigger,” make sure your content is in a logical order. Even try creating a content map for each trigger campaign. Also consider the length of the campaign vs. the timeliness of the content and don’t include irrelevant content just to take up space.


Triggers should always focus on the goal with all content pointing to the same outcome or call to action.


The Most Incredible Addition to Power up Your Inbox: Multi-Account Support

It’s now 8 months since the Mailbird beta launch and, already, thousands of new users join the beta program every week, predominantly coming from the U.S. and Europe, and a few in Asia. And here is one thing that will surely turn those thousands into millions very soon: the newest and long awaited addition to the Mailbird email platform – multi-account support!


Multi-account support is what separates web mail from desktop email clients. This is the number 1 reason people migrate from web mail to native email clients. This is how people gain more control and get a beautiful email experience that is fast and fully integrated with their PC and laptop OS. Finally you can eliminate having to keep annoying multiple tabs open, constantly having to log in and out of different accounts. You can now have a productive work flow while easily managing tons of information that come through your multiple email accounts each day. Starting today, all those online inboxes now have a solid central hub inside Mailbird – the email client that is often, and rightfully, referred to as “probably the best email client for Windows.”


The cool, international email team of Mailbird and many native email client users on Windows know that this is the biggest launch since the Mailbird beta went public. In a billion dollar market for native email clients for Windows, this one hits the nail on the head. Other email products out there today are either too expensive, don’t work properly, don’t support IMAP or have multi-account support. There is an underserved market for really great email clients on the Windows platform.


Current email clients for Windows OS today include Outlook, Thunderbird, Postbox, Inky, Opera Mail, Em Client and more. With pros and cons to all, a lot of these clients take a particular focus on changing the way email looks, reprioritizing how emails are sorted, creating an actionable to do list from the inbox and other features that desktop email users are keen of. It will be interesting to watch where email goes in the future and how these email client companies will compete on improving email for the world.


Additionally, with email as a global product, retargeting the Asian market for the first quarter of 2014 should unveil behavioral interaction differences. When it comes to email, Mailbird among other email clients are ready to stir things up with growing email trends on mobile and web. A prominent market in Asia is Indonesia. With a population of approximately 250 million who are extremely active online, more so than Western markets, there is a large potential for email client game changers that are innovating with today’s online social and productivity culture.  Mobile and web environments for email are the desktop’s sidekicks and only further boost that awesome “in control” feel you only get with a rock solid email client.


With tens of thousands of Mailbird signups since the beta launch, it speaks volumes to the many problems with email today. Some of the typical email problems we hear about today include complaints about how email is sluggish, old technology that hasn’t changed, it is distracting when you are working, it is ugly and the list goes on.


Exploring the Asian market for email is sure to bring many new insights into native email client behavior.


Limitations of Securing Email With PGP

PGP, (pretty good privacy) technology has been used to secure email communications since the early ‘90s.  Available both as freeware and commercially, PGP is the most widely used privacy-ensuring tool by both individuals and corporations.


The PGP design has not changed much since it was first introduced over twenty years ago, requiring each PGP user to have a publicly known encryption key and a private key known only to that user. Messages are encoded using a recipient’s public key, and then decoded using the recipient’s private key. This method, although highly, secure can have several limitations due to its design.


Here are 10 challenges that limit the effectiveness of PGP technology when deployed at enterprises:


1. PGP keys maintenance can be an administrative nightmare - each public and private key has its own expiration date that needs to be maintained.  In the event there is a technical failure resulting in a lost key, all the data that was encrypted with that key is lost forever. To maintain enterprise grade keys management, organizations are required to deploy a keys backup system requiring IT time and resources.


2. Organizations cannot secure large files using PGP - in most cases, email messages with file attachments that are larger than 10MB may double in size to 20MB after PGP encryption, exceeding the maximum allowed message size by the enterprise email gateway or the centralized PGP server.


3. Enterprises can share emails securely only with other organizations that use PGP -  if the recipient isn’t using PGP and does not have a public key, an encrypted message can’t be sent, therefore ad-hoc users cannot receive secure emails


4. No email receipt confirmation with PGP - the sender of a PGP based encrypted email does not receive a confirmation from the recipient that the email was successfully delivered and decrypted.


5. Cannot scan incoming PGP email with  anti-virus - in order for a message to be decoded it must go directly to the recipient without the email or the attachment being scanned by an anti-virus. To overcome this threat, organizations are required to deploy a decryption gateway server, which results in an additional costs and IT staff efforts.


6. Sensitive data stored in the DMZ - enterprises that choose to deploy a centralized decryption gateway server often deploy the server at the DMZ where emails and the attachments are decrypted before being sent to a data scanner tool. This creates an opportunity for attackers to gain access to sensitive data that is stored insecurely in the DMZ and is a significant blind spot in the organization’s data security.


7. Limits access to additional security tools - regardless of whether the PGP deployment is utilizing a centralized decryption gateway server, it cannot be integrated into a secure business workflow that makes use of additional tools such as DLP that can process/manipulate the emails and their attachments before sending them out of the organization.


8. Uncontrolled Access to email after delivery - the sender of a PGP encrypted email cannot set an expiration date for the message and its attachments, or limit the number of email views and limit the number of attachments downloads. This means that an organization’s sensitive data can be viewed insecurely by additional recipients in an uncontrolled manner.


9. Cost of maintaining client software -  cause by the fact that in most PGP based email implementations, the enterprise chooses to install a client for each one of its email users. Even if the enterprise deploys a centralized gateway server there are additional IT costs.


10. Maintenance costs of PGP based encrypted emails are high -  these costs include the cost of dedicated hardware, real estate, software licensing, service, support and user training.


By integrating a secure mail solution with a file synchronization and sharing solution, organizations can eliminate the need for complicated key maintenance and additional IT costs while benefiting from additional security features.


Once sent, the encrypted email and the attachments are stored in the virtual safe of the sending organization.  The recipient receives an email that contains only a link to the stored email at the sender’s organization, plus a one-time password. Emails can be secure after delivery including the ability to limit making the email view-only, limiting the number of attachments downloads and setting an expiry date for the email.


There is no need for systems to manage private and public keys, the sensitive data does not reside in the DMZ, and additional security measures such as DLP and data scanning and work uninterrupted.  As a result, the organizations’ sensitive data is more secure with lower maintenance and operations costs than comparable PGP solutions.


More Messages, More Problems: How Businesses Can Send Fewer, Better Messages


1) Consumers suffer from message overload — and a lot of the messages we get are annoying and irrelevant.

2) This is not just a problem for consumers to deal with — it’s a problem for businesses. The more they annoy customers, the less likely people are to stick around.

3) Consumers keep adding new inboxes-email, SMS, push, social. For every channel, businesses have to add a new piece of message infrastructure.

4) But as businesses layer on new ways of sending messages, the new tools don’t coordinate with the old ones. This leads to crowded inboxes and a poor experience for customers.

5) The next generation of communication companies will do for businesses what designers did for webpages: cut down on the quantity of information, creating whitespace so that messages actually get noticed. This is what Outbound is building.


Inboxes are like Tetris

Think about your inbox. What comes to mind? For me, the image is a marathon game of Tetris. I can find better ways to deal with the inflow-I can install Mailbox, do some filtering, be disciplined about touching every message only once-but it just keeps coming. What would it take to replace Tetris with a different image?

The short answer is that businesses need to start thinking about messages as extensions of their product instead of one-off blasts. The end-result would be fewer, higher-quality messages-and a lot more whitespace around key information. We need to do this for the inbox:

In order to understand how this would work, let’s take a step back and look at how businesses send messages now.


Why the messages just keep coming

The mold was set with email, which has become the universal channel. We get messages from mom alongside flight details and promos from The Gap. As long as there are 1-to-1 messages from people we know waiting for us, we’re not going to stop checking our inbox, and that makes it a very attractive channel for businesses. As a result, the 1-to-1 messages that draw us to email in the first place make up a smaller and smaller portion of our inbox, and we spend more time sorting and less time consuming information that matters.

But that was only round one. Just as email became ubiquitous and started to reach a saturation point, we all got mobile phones. We started off texting our friends, but it wasn’t long before businesses realized that by collecting our mobile number they gained a new channel-inbox number two. We soon upgraded to smartphones with app stores, and we added a third inbox for push notifications.

As each of these channels approaches saturation, it doesn’t go away. New channels just get stacked on the preexisting channels and find new ways to compete for our attention (I’m looking at you, badge app icon!)

Our inboxes didn’t fill up on their own-it took several generations of new infrastructure to enable businesses and nonprofits to message us so steadily and efficiently. Here’s how it got so easy to send messages:


Generation 1: Age of the email service provider

It used to be that when you wanted to email a group of people, you had to type a lot of email addresses into the “To” field. Sure, you could set up a listserv, but that was the domain of the webmaster/admin technical guru, not a task for the common man. And even the listserv was a pretty basic tool. But when Constant Contact, MailChimp, and a dozen other email service providers (ESPs) came along, they not only democratized the listserv, but also made it a lot more powerful by adding open and click analytics, scheduled messages, unsubscribe tools and list segmentation.

Over the past fifteen years, at least six ESPs have grown up to be worth more than $100 million by making these features accessible. These companies opened up the playing field by allowing anyone to do email marketing. As ESPs grew, the best ones realized that they needed to protect end-users as well as serve their customers. The leading ESPs enforce strict opt-in and unsubscribe policies and spend a lot of time educating customers about the right way to do email marketing. MailChimp leads the market (folks on Quora estimate that MailChimp may be worth as much as $1 billion) in large part because of its attention to the kind of email experience its customers are creating for their contacts.

But even ESPs that respect our inboxes can’t manage the new flood of messages from the product across email, text and push.


Generation 2: Rise of the transactional message

As the market for ESPs matured, transactional message providers like SendGrid began offering tools that let developers outsource some of the email drudgery involved in delivering transactional email. Developers still had to define the business logic to trigger receipts, invoices, app content (like new comments) and other product-based emails, but they no longer had to worry about delivery.

Easier delivery seems like an incremental improvement, but it opened up a flood of transactional email: last year SendGrid reported that “web applications are sending an average of 631,000 emails per month, and nearly 50 percent of user actions in web applications trigger an email alert.”

And that’s just email. Twilio is building an empire around SMS and voice delivery, and Urban Airship is doing the same for push notifications. Both of these companies tout better engagement compared to increasingly lackluster email open rates. But as these channels saturate, their engagement rates will erode the same way that email has.


Where does that leave us?

Businesses are sending more messages using more channels than ever before in an effort to capture our attention. Consumers battle a constant flow of messages coming at us across channels, constantly sorting and skimming to separate the signal from the rising noise. We’re all stuck playing a frantic game of Tetris with our messages.


The next generation of message tools will create… whitespace

How did we move past cluttered websites toward beautiful pages with abundant whitespace and intuitive user experiences? We did it by stepping away from our keyboards long enough to listen to users. What do they think of the page? Where do we lose them?

Message tools need to create whitespace around the messages businesses send in order to help people stop and pay attention. Here are some ways to achieve this:

Begin with the user’s context, not the channel. Most businesses start by deciding which channels they will use to send messages, then gradually fill those with messages to push content out. Instead, start with the context: where and when will this person receive the message? Is the call to action (even if it’s just to absorb information) reasonable given this context? A lot of this involves A/B testing-quick iterations through trial and error-but some of it is common sense.

Pay attention to the relationship. If you’re barraging customers with messages or leaving them in the dark, it doesn’t matter how interesting the content is; those people are probably too annoyed to pay attention. A single, unified view of all the messages going to each user across channels and departments allows you to see when you are over- (or under) whelming people.

Give users a say. Analyzing user data helps address both of the points above, but you’re never going to get the full picture of a user from analyzing her data. Just as user testing and feedback often yield surprising insights about how to make a webpage better, we need to gather feedback on messages that is much more fine-grained than an on/off unsubscribe button.


Where to start?

In small companies, these principles produce slight differences in messaging, but over time those differences multiply as message volume and organizational complexity grows. It will take time to build really good solutions to these problems. My company, Outbound, has begun with three simple innovations:

1) We separate message content from channel so that any information can be sent, using any channel, based on the actions that users take. That leaves your options open depending on the context for your message.

2) We log all outbound messages in one place, providing a unified view-the same view your user has of her inboxes.

3) We make automated messages code-free because it’s impossible to iterate quickly based on trial and error if the person who is writing the messages is always waiting for engineering to make edits or change business logic.

This just scratches the surface of what we need to help businesses create fewer, higher-quality messages. But that’s why we’re so excited about this space. Imagine if instead of optimizing for more clicks, companies had a tool that optimized to make you totally satisfied-and kept changing their message mix until you signaled that you were happy. That’s the inbox I want.