Selecting a Salesforce Email Integration

Sync Salesforce With Outlook or Gmail

Effective Sales Management Depends on Keeping Salesforce Data Current and Accurate.

This starts with the right salesforce email integration.

Salesforce™ has revolutionized the way sales teams operate.

It has become the central database of information that sales reps rely on to do their jobs effectively. Sales leaders also rely on this critical data in order to make precise sales management decisions.

However, if the data being entered into Salesforce is incomplete or inaccurate, management becomes challenging and forecasts become unpredictable and inconsistent, at best.


The benefits of having accurate sales data are clear:


Your sales reps always know how to prioritize their pipeline


Managers know where to focus to improve team performance


Sales leaders can easily see the data they need to optimize strategies and goals

Unfortunately, keeping Salesforce data accurate and up-to-date is an uphill battle.

The process of manually entering sales activity and customer data into Salesforce is often extremely tedious and frustrating, decreasing the chances that your sales reps will actually take the time to do it.


While getting sales reps to enter accurate and thorough data is an ongoing struggle, you simply can’t afford to not have this data.

The only real solution is to find a way to eliminate manual data entry entirely and make the whole process automatic.

Ideally, your sales reps would never have to even open Salesforce. They could perform their work as they normally do, and all of their sales activity and customer data would be synced from their email inbox and calendar to Salesforce automatically.

Fortunately, many products in recent years have been developed to enable this capability. In fact, there are now so many options for integrating email with Salesforce that it has become difficult for many sales teams to decide which one is the best fit for their specific needs.

In this guide, we’ll cover the 5 most important criteria sales teams must use to evaluate Salesforce email integration systems so you can make the most informed decision possible.

In addition you will have access to a breakdown of the differences, strengths, and weaknesses of the top Salesforce email integration tools that you can use for reference in your research.

Selecting a Salesforce Email Integration For Gmail & Outlook: Criteria


In 2018, Steve Roch and his team conducted an independent study of the top Salesforce email integration tools.

Steve is a CRM expert with 14 years as a Chief Information Officer for a software firm which relied heavily on CRM and email integration before founding a highly successful CRM practice, CRMCulture for 8 years.

Over the course of 6 months, Steve and his teams installed each application to test user stories, performance, and usability. They identified 5 main criteria to evaluate the performance of Salesforce Email integration solutions.

They found that this same criteria can be used when selecting an email-Salesforce integration for your organization:

Email-Salesforce integration

Email Environments Supported

Especially when evaluating Microsoft Outlook solutions this category is important because even if a vendor does support the particular version/environment one is looking for, the total breadth of version support is an important indicator of how that vendor will support future versions.

Performance & Stability
Basic Salesforce Integration
Advanced Features
Security and Storage

Let’s explore each criterion in more detail.

Email Environments Supported


There are many variables to consider when integrating email and calendar with Salesforce as there are various email clients in the market – Outlook being the most complex as it comes in a variety of versions for Windows, Mac, Web and Mobile.

Adding further complexity, depending on the version of Microsoft Outlook or Exchange Server you use, only certain methods of providing a sidebar (aka side panel, plug-in or extension) will be able to support your needs through the available API’s from Microsoft.



Email, Calendar and Mobile Integration with Salesforce Workflows

Although every organization will have different needs with different priorities some of the most common email tasks you will want to evaluate are:

Most Common Email Tasks

The ease of linking of inbound/outbound email and calendar items to the Salesforce contacts/leads with special attention to multiple contacts on the To/Cc

Evaluate how good of a job is the system you are evaluating at handling multiple contacts on the To/Cc line. Does the system pull information for the multiple contacts in their initial side panel?

Ease and completeness of linking inbound/outbound email/calendar to opportunities and custom objects
Creation of new Salesforce records; leads, contacts, accounts, opportunities and custom objects
Completeness of the side panel as a fully working Salesforce environment, including interacting with related lists and having a side panel for the calendar
Navigating, searching and updating Salesforce without leaving the native email or calendar interface
Linking documents/attachments
Mobile Phone Clients

Email Clients Supported

Email Clients Supported

Another important criteria is simply the number of email clients supported. Beyond just looking at whether or not they support your particular email client, support for a large variety of clients is a predictor of the future stability, performance, and innovation capabilities of a vendor.

In fact, most Salesforce consulting partners and their customers prefer not to navigate through these complexities and would prefer a single vendor who can support their integration requirements regardless of email environment as email clients and services are upgraded or migrated.

Email clients supported may include:

  • Outlook Desktop 2016
  • Outlook Desktop 2013
  • Outlook Desktop 2010
  • Outlook 2007
  • Office 365 Web Client
  • Outlook for Mac
  • Gmail
  • Mobile clients

Outlook Desktop, Office 365, and Outlook for Mac 2016

When comparing Outlook support, you need to look at mainly two factors:

  1. Outlook Client Support (Desktop and Web)
  2. Outlook Support with Exchange Server, Terminal/Citrix Server, or Published Desktops

Additional Outlook criteria to consider:



If your organization relies on Google’s email and calendar apps, there are a few criteria you will want to keep in mind when making your evaluation:

Chrome Extension
Linking Activity to Salesforce Contacts
Interface and Features
Calendar Sidebar
Refresh Rate
Caching Issues

Mobile Support

In addition to providing a side panel (or plug-in) for email systems, check if your vendor also provides a mobile phone version of their product offering a similar experience to that of their Side Panel and delivered via both Android and iOS.

The main evaluation criteria for mobile options are:

Support for both iOS and Android devices
Outlook Add-In
A fully functional email client
Ability to capture email to the associated Salesforce records
Ability to select contacts on To/Cc/From lines and view Salesforce data
Ability to search for and initiate new email to existing Salesforce contacts/leads

Performance, Stability, and Implementation


Performance and stability are perhaps the most important features to consider for an application as it needs to be fast and stable otherwise its features won’t really matter.

It’s also important to gauge the amount of technical support that may be required. Most larger orgs will sacrifice features for stability to ease their implementation and support burden.


Performance, Stability, and Implementation Criteria


Refresh Rate: How fast is the system at retrieving and pushing data to/from Salesforce?

Caching: Does the sidebar experience caching issues when navigating through emails quickly, or performing certain actions and then moving on to another email? Does the side-panel refresh properly when the user is rapidly spinning through emails and when linking an email to a 2nd contact (this is a common problem with browser-only technology)?

Stability: Does the sidebar disconnect or log the user out after a period of inactivity? Does the sidebar ever disappear or fail to load?

Ease of Implementation / handling of custom objects: Is there any special configuration required to expose Custom Objects and Fields? Some products require the use of a configuration tool to turn on Custom Objects on a per-user basis, which is an extremely time-consuming task for large enterprises.

Customizations: Does the product allow you to hide certain fields on a per-user basis? Can you hide the Opportunities section (if you don’t use it)? Can you redefine the values displayed in the related lists? Are changes to the sidebar layout propogated to all users, or do you have to export the changes and import them individually for all other users?

Basic Salesforce Integration


When it comes to integrating email/calendar with Salesforce, what you have to consider is whether the user will be able to have some control, or if the solution is fully-automated.

Generally the former is preferred because fully-automated solutions that link emails and calendar items automatically, without any user interaction, are prone to creating a lot of duplicate and junk data in Salesforce.


Side Panel Evaluation

Be sure to evaluate the ease of use and completeness of the side panel as a fully working Salesforce environment, including interacting with related lists, and having a side panel for the calendar.

In general, side panel apps can be categorized into two distinct approaches in their initial view of the side panel:

  1. List of all Contacts: Those that initially show all the contacts on the To/Cc/From line in a list and then allow one to drill into specific contacts to see more detail.
  2. Single Contact: Those that show the detail of the first contact found on the To/Cc/From.

Most users find that it is much more important to see the list of contacts/accounts/opportunities (known and unknown to Salesforce).

In particular, the 2nd approach often causes users to miss key contacts, accounts, and opportunities otherwise shown in the first approach.

Additionally, the first approach is superior for the task of quickly linking the email. Vendors that use the list approach make it simple to link the email to all of the various contacts and other Salesforce objects


Basic Salesforce Integration Criteria

You will want to evaluate products according to the following most common tasks and workflows a typical sales user performs as part of their day-to-day email and Salesforce work:

Most Common Tasks and Workflows

Salesforce Search/Edit

How well does the product handle navigating, searching and updating Salesforce records, without leaving the native email or calendar interface?

Record Editing/Creation
Contacts View
Detail and Related Lists
Linking Process
Opportunity Display/Linking
Attachment Handling

Advanced Features


The research revealed a high degree of variation amongst the vendors for advanced features.

When evaluating products, keep the following categories of Advanced Features in mind:

Sales Enablement & Acceleration

Sales enablement and acceleration features are the collection of features such as:

  • Email Templates & Short Cut Text
  • Send Later or Scheduled Email
  • Remind me if no response
  • Batch Email

Calendar Availability Tools

Calendar Booking Tools are now critical in the sales workflow and most of the vendors now offer options for making the users availability known to the customer and also allow the customer to then book a meeting, without all the back and forth emails.

There are two approaches that the vendors take, each with their own pros and cons:


The Fully-Available Calendar as a link


The absolute best customer experience. Empowers the customer to pick a time that is convenient for them.

Embedding the pnk in your signature “Book a Meeting” is a one-time only event.

The customer is more pkely to find a time that works for them and ultimately the meeting is more pkely to get booked than pushing them for a certain day/time.

Well suited for early lead development when getting the meeting is more important than a big push for a specific date/time.



The user needs to keep their calendar accurate and block out times that they don’t want to meet. However, we find that it’s not a big deal once the meeting is booked to change the time, 99% of the time the customer accepts the new time.

A calendar with a lot of open meeting slots can give the customer the impression that you aren’t very busy and therefore not in demand.

With most products, the meetings generated are named with generic subjects requiring the user to then update the Outlook Meeting to something meaningful after it has been created.

The Time-Picking or Choose Availability method.

Sales user picks specific time slots and those are offered as buttons in the email.


Sales users surveyed initially preferred to pick the times rather than offering a wide-open calendar. They believe that it’s the job of the salesman to drive the customer to do what they want to do and on their timeline.

However, we mostly found this was just an insecurity in having the full calendar published even though no details are shown.



This often provides a poor customer experience, as you are pushing the customer into timeslots that may not work for them, or when they get around to picking the slot, the time slot is no longer available.

If the sales user doesn’t offer up a suitable time slot, it’s back to the same old game of emailing back and forth for a mutual time.

This method is considerably more time consuming for the user to pick time slots.

Often, the times chosen are no longer available when the customer eventually gets around to booking the meeting. Most vendors handle this scenario well, though, and do not allow double-booked meetings, but it is indeed frustrating to the customer.


Automatic Email/Calendar Sync to Salesforce

Many customers and specific industries require every email interaction and calendar item to be captured in Salesforce. Not many vendors offer the capability to do this automatically.

A few vendors offer a solution both on the email side (where emails automatically link to opportunities) and on the Calendar, where they make a distinction between meetings with and without attendees (so that if desired one can disable sync for calendar items that aren’t customer related, i.e. Doctor’s Appointments, Job Interviews, etc).

If your organization needs to capture email interactions and calendar items in Salesforce, make sure that the product you’re considering offers the ability to sync these activities automatically.


Marketing Automation

Very few solutions offer any sort of Marketing Automation type features, but here are a few to keep in mind:

Intuitive Batch Email: An intuitive batch email feature utilizes email templates to send batch emails to multiple contacts at once.

Automated Email Campaigns: This feature allows users to place contacts onto an email campaign that automatically executes pre-determined emails at specific intervals, similar to more robust marketing automation solutions.



Many vendors offer Email Open tracking or notifications, as well as Link tracking features. Here are some criteria to consider when evaluating products with Analytics capabilities:

False Positives: Does the product create a special code as to not report false positives (such as opening your own sent mail)?

Aggregate Reporting Per Contact Does the product provide aggregate reporting per contact? Or, can you only see analytics when re-opening the same email?

Security and Storage


Integrating your email and calendar with Salesforce poses the risk of creating security vulnerabilities, especially if the integration tool requires access to your company’s Exchange server credentials in the cloud.

Some products require global impersonation, giving admins unlimited access to every single mailbox on your company’s Exchange mail server. This kind of direct server access is inadvisable, as it could potentially expose your network to unauthorized individuals.

Make sure that the product you’re considering provides enterprise-level security, where connection paths of data are completely configurable and secured with single sign-on (SSO).


Single Sign-On (SSO)

According to OneLogin, single sign-on (SSO) is “a system that enables users to securely authenticate with multiple applications and websites by logging in only once—with just one set of credentials (username and password). With SSO, the application or website that the user is trying to access relies on a trusted third party to verify that users are who they say they are. Authentication requests and information are passed using standard, secure protocols, such as SAML or OAuth.”

A common example of SSO is a website, service, or application that allows you to sign in using your existing Google or Facebook account, rather than having to create an entirely new account.

According to Salesforce, there are many benefits to using SSO:

Reduced administrative costs: With SSO, users memorize a single password to access network resources and external apps. With fewer passwords to manage, system admins receive fewer requests to reset forgotten passwords.

Time savings: On average, users take 5–20 seconds to log in to an online app. It can take longer if they mistype their username or password and are prompted to re-enter them. With SSO in place, manually logging in to an application is avoided. These saved seconds reduce frustration and add up to increased productivity.

Increased user adoption: Due to the convenience of not having to log in, users are more likely to use the application regularly.

Increased security: All password policies that you’ve established for your corporate network are in effect for the application as well. Sending an authentication credential that’s only valid for a single time also increases security for users who have access to sensitive data.

In particular, check to see if the vendor you are evaluating provides SSO, and allows you to sign into your account using your Salesforce credentials, instead of creating specific credentials for their product.


Additional Security Considerations

You will want to evaluate products according to the following security considerations:

Data Encryption: Is all data fully encrypted both at rest, and in transit? In particular, check for Transparent Data Encryption (TDE). TDE is a technology employed by Microsoft, IBM and Oracle that encrypts the data within the physical files of the database; the “data at rest”.

Dynamic Data Masking (DDM): Is exposure to sensitive data limited by masking it to non-privileged users?

OWASP Compliance: Is the product compliant with the OWSAP’s best practices and guidelines for application security?


Data Storage Considerations

You will also want to evaluate how the vendor handles data storage. Ideally, the product should store the bare minimum amount of data possible to provide the feature. In order to ensure the security and privacy of your data, make sure to ask about the following:

Integrating your email and calendar with Salesforce can help achieve several related objectives in your organization:

  • Does the vendor’s sidebar store your Salesforce data?
  • Does the vendor’s email sync feature store the body and attachments of your emails, or just the meta-data?
  • Does the vendor’s email and web visitor tracking store these records, or just the meta-data?
  • Does the vendor’s calendar scheduling tool store these records, or just the meta-data?
  • Does the vendor’s mobile app store your email and Salesforce records, or just the meta-data?



Integrating your email and calendar with Salesforce can help achieve several related objectives in your organization:

  1. Increase data quality:  With more complete and accurate sales activity data, you are able to increase sales capacity, validate forecasts, and make better decisions overall. However, consider what it takes to get this data. Data quality will not improve by asking sales reps to enter more data into the CRM. Whatever solution you choose needs to be transparent for the sales reps and do the work of automatically capturing this data for them.
  2. Improve the performance of reps: Better data means better customer engagement insight for reps, which helps them prioritize their daily work. By bringing Salesforce to the inbox, and adding automation functionality, sales reps will have better insight into every customer, and will be able to focus their efforts on those customers with the higher probability to close.
  3. Eliminate non-selling time: By eliminating data-entry and admin activities, you can put that time back towards selling. This alone can increase sales capacity by 33% or more.
  4. Manage sales based on data: Sales activity is the best predictor of sales success, and as such, having complete and accurate data for sales to optimize their territories and manage sales rep performance is critical for optimizing sales capacity.

As you evaluate solutions, look beyond the vision and promises of each vendor, and use this guide to determine their true ability to provide you with a seamless solution that isn’t hindered by performance or security issues.

We hope that this ultimate guide helps you see past the hype and sales pitches, and helps you understand the true strengths and weaknesses of each solution.

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