Leader in Sales Email Tracking Expands Analytics with Prescriptive: Interview with Andrew Archer, VP of Marketing at Yesware

Emily Sue Tomac
December 8, 2015

Leader in Sales Email Tracking Expands Analytics with Prescriptive: Interview with Andrew Archer, VP of Marketing at Yesware

We talked to Andrew Archer, VP of Marketing at Yesware, about the developing Sales Enablement software space. Yesware combines email tracking, sales intelligence, analytics, and productivity features (such as email templates and click-to-call) into a tool that’s designed to service salespeople as well as managers/ops. A pioneer in the sales email tracking space, Yesware is expanding its core by building out more in-depth analytics and prescriptive recommendations, which Archer said will increase the actionability of Yesware’s data and help improve sales performance. He also gave us a view on upcoming product releases—including how Yesware’s development roadmap fits into larger trends in Sales software and best practices. In addition, Archer responded to reviewer feedback around Yesware pros and cons, explaining Yesware’s approach to common pain points compared to its closest competitors.  

Introduction to Yesware

Give us an introduction to Yesware—where do you see yourselves in the space, and what is your mission?

Our space is evolving rapidly, and it’s been called a couple of different names: Sales Enablement, Sales Acceleration, and Sales Productivity. All of these terms fall under a larger umbrella term—Sales Automation Software. We see Sales Automation as a macro category that contains CPQ software, sales content management tools, sales performance management platforms, and sales productivity solutions. We fit into that last bucket.

Yesware is a leader in the space. Our mission as a company is to increase the amount of time that salespeople spend actually selling their product. A recent study showed that salespeople only spend 35% of their time on sales.  We want to help them grow that percentage, and make more effective use of their time in order to close more deals faster.

What trends are you seeing in the Sales software space, and how do they play into your value proposition?

We’re seeing a larger trend around the consumerization of business technology, and it’s particularly prevalent in the Sales software industry. Software is designed to be very user-friendly, and to grow from the bottom up within an organization (as opposed to top-down adoption). So Yesware focuses on providing accessible, actionable data for the salespeople who are driving revenue.

Yesware’s value proposition is two-fold:

  1. We surface data for decision making to sales professionals and sales managers.
  2. We also provide them with the tools to take action on those insights.

Specifically, Yesware provides tracking information, so that a salesperson knows when a prospect is reading their emails, looking at presentation slides, etc. Yesware also tracks which individual slides a prospect spends the most time on. Then we provide productivity tools so that the salesperson can immediately act on that information—our click-to-call functionality, for example, or email templates that help reach a larger group of prospects more quickly.

Sales Productivity & Prescriptive Advice

Can you give us a more granular view of where Yesware fits into the Sales Enablement landscape?

I would say there are three main emerging subsets within Sales Acceleration or Sales Enablement: productivity, predictive insight, and prescriptive advice. At a granular level, we view ourselves as a productivity and prescriptive solution.

Yesware is pretty dominant in the sales productivity space, since we pioneered email tracking four years ago. Our template features and click-to-call both also fall under productivity.

But we are expanding into prescriptive advice, which is a major differentiator. It’s a newer piece of the Sales Enablement space. It’s great to have data, and there are several solutions out there that can help surface data in Salesforce. However, we see a gap in terms of actionability—software needs to empower users to do something with the data. Yesware is addressing this with prescriptive advice, by recommending specific actions and then providing the tools for salespeople to take action on their data and follow up with prospects. These are newer features that are coming out in the next few weeks. 

Do you offer prescriptive analytics based upon data surfaced within Yesware tracking, or does Yesware integrate with predictive analytics tools?

We process prescriptive internally. With all of the tracking at Yesware’s core, we’re able to see the email activity ourselves. We are able to see when a prospect opens an email, which links they click, which slides they spend time on, etc. We use that activity data to populate an Activity vs. Engagement Report. It will scatter plot all of your prospects, as well as their level of engagement based on these activities. Users can visualize what’s working and what’s not working, as well as determine which prospects might need a different tactical approach and which prospects might not be a good fit. That’s a specific example of how we can leverage activity data and recommend an action to sales reps. It’s all done internally using our own database.


Yesware Customer Base & Key Use Cases

Who is your target customer? What buckets do you see within your customer base?

Over 700,000 sales professionals are using Yesware today. Our customer base ranges widely, from sales individuals—like real estate agents, who operate completely independently—all the way to companies like Groupon, a multinational corporation that has its entire sales team using Yesware. It’s great to see that the value is there across a breadth of organizations.

What do the different use cases look like across your customer base?

There are two primary users of Yesware, which correlate with our different levels of product. Our lower tiers (Pro and Team plan) are excellent at serving SMBs, who may not be using Salesforce as a CRM, but are looking for extra tools to help make their sales teams more effective. That represents almost 70% of the Yesware customer base, in terms of overall volume. It’s a natural distribution since there are a lot more small businesses out there in the marketplace.

Our other customers are much larger organizations that need integration with Salesforce, so that reps can automatically track their activity data. We make sure all of their data is entered into Salesforce, and their sales operations teams can make better decisions based on that trusted data. Right now, this use case applies to about 30% of our customer base.

What is the user experience for Yesware data that is surfaced in Salesforce? Is it similar to the user experience for Yesware tracking in an email client?

Yesware lives within the user’s Gmail or Outlook interface, because that’s where salespeople primarily work—we find that salespeople don’t tend to like living in Salesforce as much. Activities are tracked within the user’s email client, including click to call (we have a phone product as well). Then all of that activity—calendars, calls, emails, link clicks, presentation engagement—automatically syncs into the Salesforce back end. The integration is out of the box; it requires no custom implementation. But users can customize and surface or manipulate that information in different ways, for example, if a sales operations team wants to report on it in a different way. It essentially populates activity into the contact history of the Salesforce contact.

Yesware vs. Marketing Automation Tools

What are the major differences between Yesware and email marketing or marketing automation tools?

Email tracking tools for marketers are designed around one-to-many interactions. Users want their emails to be as customized as possible, but the reality is that they’re communicating with a macro group of people because they want to reach as many prospects as they can. By contrast, salespeople are focused on one to one types of communication. That’s where the major differences lie.

Some metrics are important to both sets of users, such as open and reply rates. Marketers and salespeople both need to see which templates have the highest click-through, reply and engagement rates. Those features are similar between the two systems.

Where Yesware stands out for sales, in particular, is with the extra features around individual customization and ease of customization. For example, if you needed to reach out to a list of 100 prospects, you could upload list and then customize a message within mail merge for every single one of those people. Our goal is to provide that level of granularity quickly and easily, interfaced in pure email. Yesware enables salespeople to send custom messages in a very easy, effective fashion.


Does Yesware have automation around email sends and customization?

We do have a feature that allows users to create a multi-step email drip or nurture campaign, which will automatically stop when someone replies to the email chain. But the bulk of our philosophy is that sales reps need to steer personalized communication. We don’t automate the customization aspect.

We also have a new product that will be released in Q1, which will take customization a step further. It uses prescriptive analytics to make very, very specific customization recommendations. Yesware will say, “Here’s the recommended template, would you like to send it? Just click send.” This will leave ultimate control to the salesperson—basically, customization will be as automated as possible without actually automating the process—because we think it’s important to retain that human element.

Where do you see Yesware’s approach to personalized communication being most important?

It becomes more important for certain types of organizations than others. For example, a B2B software company is much more inclined to have salespeople engage prospects because their sales cycles involve more education and complexity. They need more unique sales interactions, because of the complexity of the product. For other companies with simpler products, the sales cycle might be more self-serve. That’s where I think marketing automation plays a larger role.

Those are the two ends of the spectrum, but there’s a huge gray area. Most of our customers use both tools. Where marketing automation ends, Yesware picks up—that’s how we think of our position in the technology stack.  We see the systems as different but complementary. Our information can be surfaced in Marketo via the Salesforce integration, and vice versa. The Marketing team uses marketing automation for demand generation, in order to capture leads based on some filtering criteria. Then they pass those leads to the Sales team, and at that point Yesware kicks in as the tool that sales reps will engage with to manage the leads they’ve been handed. We play nicely with marketing automation.

The Competitive Landscape

Who do you see as your competitors, and how would you describe the competitive landscape?

I see Yesware as a clear leader in email tracking, which we pioneered, and Sales Acceleration, since we combine sales productivity and prescriptive advice.

InsideSales is an example of a similar tool, although they are not a direct competitor. They’re more of an adjacent solution since they are rooted in phone calls, teamwork, and sales training.

In terms of direct competitors, we see a few smaller companies: Tout, SalesLoft, and Outreach. In the last year or two, they have started to build features that directly compete with Yesware. Each of these solutions has different strengths and focuses. For example, SalesLoft is focused on the prospecting side, whereas Yesware focuses on both prospecting and closing deals, and Yesware is designed for the full sales team, as opposed to just one section of it.

We used to see HubSpot’s Sidekick but their product development has put them on the path to really compete more with Salesforce. Their Sidekick product has become a CRM in and of itself, as a complement to their marketing platform, so we don’t see them as much as we did a year and a half ago.

How do you differentiate from your direct competitors?

We differentiate in a few areas:

  1. We are the leader, in terms of number of customers and our establishment in the marketplace. We’re on the innovating side, whereas I think our smaller competitors are on the catching up side, particularly with the tracking features.
  2. We are building a platform to service the full sales team, rather than just one sales use case. Historically, Yesware features have been around inside sales—the product worked for prospectors, closers, and even SDRs. Our new analytics product serves the sales manager by surfacing all of the combined sales activity. It makes recommendations on how they can coach their team. Yesware will be able to tell managers which reps have better engagement, templates, and reply rates at a team level. We also have a one on one report coming out, to help managers coach individual reps. In Q1, we’ll be releasing another product that can take that analytics data and marry it back into sales productivity.

Our robust features and product development roadmap differentiate us from the competition.

Is the enterprise space a growth area for Yesware?

Yes, absolutely. Enterprises tend to adopt new technologies a lot more slowly than smaller businesses. With the space as new as it is, more enterprises are just starting to become attracted to our technology. Google Apps enterprises, like Groupon and Zenefits, have been early adopters of Yesware and Yesware-like technology. I think we’ll see Yesware grow in the enterprise space as time continues.

A year and a half ago, Yesware launched an Outlook product extension that is more catered to the larger end of the market. Since we’ve launched Yesware for Outlook, enterprises are becoming intrigued. They are entering into conversations with us as they’re starting to adopt technologies to improve the sales process.

Responding to User Feedback: Strengths & Innovation

Tracking, your Salesforce connector, and your email templates were all mentioned as strengths in user reviews of Yesware on TrustRadius. From your perspective, how do these features of Yesware stand out?

A lot of tools do Salesforce synchronization, but there’s a wide spectrum of what that can mean—from basic fields to in-depth synchronization. Yesware developed one of the most robust Salesforce syncs on the market. We can import all fields around emails, as well as calendar syncing, which is a standout from our competitors. You can book something with a contact on your own Google Calendar, and it will sync to the Salesforce record. (There are also custom options that can be built in.) The Salesforce sync is bilateral. We have a Salesforce sidebar, which is an elective pop up within the email client, to bring back information from Salesforce within your email for easy reference. That’s another aspect of our Salesforce synchronization that really stands out.

I’ve spoken about tracking quite a bit during this conversation, but I’d like to highlight that tracking is about so much more than emails now. Yesware has the most substantial, nuanced tracking capabilities on the market, in terms of the range of situations that users can track and the accuracy of our data.

Beyond basic email tracking, we have link tracking and presentation tracking, which shows when a presentation was opened and which slides the viewer spent which amounts of time on. Salespeople can use this intel to make better presentations and tailor their future engagement strategies based on the individuals’ engagement patterns.

In terms of areas for improvement, in their reviews several users mentioned issues with availability and performance. How do you see this issue, and how is Yesware addressing this concern?

Uptime is really important for every product, email in particular. If it’s not sending, that’s a major problem for salespeople. The uptime of our tracking product is over 99%. It’s something we pride ourselves on at Yesware. We strive to ensure high quality sends.

One way in which Yesware is different from competitors is that we send users’ emails directly through their Gmail or Outlook email account. The emails don’t get sent to our server and then sent on users’ behalf (like some of our competitors, who use a third-party server). Otherwise, there is a risk with shared IP addresses and spam flagging, which can impact email deliverability.  Yesware is really against that approach. With Yesware, if Gmail or Outlook is up and running, your email will be sent. Our customers should have no email deliverability issues at all.

A few users mentioned that they would like to see improvements around follow-up tasks. What functionality does Yesware offer in terms of scheduling and reminders or alerts?

On any given email, users can schedule a time to remind themselves to resurface the email. Essentially, you resend it to yourself. Or, you can set up a “send later” if you know the contact checks their email at a certain time and you want to be at the top of their inbox. Those are two additional tools we have as part of our sales productivity suite. The future investment, from a product development perspective, will always be around improving the quality of our existing features, including those two.

As I mentioned earlier, the next few major developments will be around surfacing analytics, and early next year we’ll have some new robust interface and productivity features. I’ll share more on this as the release approaches and we’re able to lift the black veil.

Are there any other macro dynamics or trends impacting Yesware’s development plan?

One interesting thing is that I’ve been hearing some people identify a false trend, claiming that with the rise of messaging apps and internal communication systems, “Email is dead!” We’re not seeing it. Email usage is incredibly strong, even within companies. When we look at the usage data there is no trend downward on email usage. Especially in communications with individuals outside of the organization, email is by far the most used tool for salespeople.

How do you handle tracking (or not tracking) email recipients who are copied on an email? Do users have fine-grained control over which recipients are tracked, and how does this relate to internal email communications?

With Yesware, there isn’t a feature that will automatically detect an internal domain. But in each email there is a checkbox, so users can select whether they want it to be tracked or not. If you’re sending something internally that doesn’t need to be logged in Salesforce, you can un-check the box so that you won’t be flooded by notifications around that email. There are also settings within the tracking mechanism so that users can make sure they won’t be notified when they open the email themselves. So we do have some tracking settings that users can customize.

The Holy Grail is to be able to identify each individual within an email thread, even when an email is forwarded to someone else. No one has solved this perfectly yet. There are some instances when users can identify the individual, but this can become spotty when the email is sent to a group. Yesware tracking happens via a pixel included in the email, which fires generically. Users can identify recipients and their activity based on location—notifications tell you when and where the activity took place—but if the email was sent to three people in the same office, with the same IP address, this gets tricky.

Continual innovation on tracking is really important because we’re working with a complex system connected to other complex systems. Yesware has an advantage because we’ve been focused on tracking for longer than our competitors, and we’re out front leading the innovation.

To share your own user insights about Yesware, write a review on TrustRadius. For more information about pros, cons, use cases, and ROI, find and filter Yesware user reviews here. For more information about features and pricing, visit the vendor’s website http://www.yesware.com/.

About the Author

Emily Sue Tomac
Emily Sue Tomac is Senior Research Manager at TrustRadius, where she studies reviews, the technology buying and selling process, and buyers and vendors themselves. Her research aims to arm people with the tools and information they need to work better, smarter, and easier. She's on a mission to tell their stories, and drive change in how business technology is bought and sold. Prior to joining TrustRadius, Emily Sue worked on research in linguistics and the digital humanities.

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