The sales department has, arguably, one of the most deadline-driven and stressful jobs in the entire business. Owing to their packed schedule of multiple new business pitches, call reports, sales meetings, product demos, and client presentations there is very little time left to manually sort through their emails and manage the sales pipeline. This is a pain-point that Yesware, a Boston-built suite of email productivity solutions, caters to. Founded in September 2010, by Matthew Bellows and Cashman Andrus, Yesware does so by making it easier for sales teams to record and analyze essential data and thus close more deals, faster.

In August 2018, Yesware announced $15M in a new round of funding, led by Foundry Group. The company plans to deploy the invested capital in accelerating product innovation and development. Additionally, the announcement also included an update about co-founder Matthew Bellows stepping down from his role as CEO of Yesware. He was replaced by Joel Stevenson, e-commerce veteran and erstwhile COO of this promising startup. Bellows will continue as Chairman of the Board of Directors in addition to assuming a full-time role involving partnership management and spreading the word of Yesware’s product vision across the world.

On Top of Every Sales Email with Yesware

Suppose the sales team wants to see which leads are warm and which have read the emailed pitch presentation. This GDPR complaint software, lets users track which emails are open or read, attachments are download, and links clicked on. The service also offers in-depth reports categorized basis individual, location, and even device type. This is only one of Yesware’s many functionalities.

A veteran sales manager, Bellows realized, some 5 years ago, there was a need for something like Salesforce but with the ability to extract the data on sales activities and share it with the rest of the organization. That there wasn’t yet a good enough software that could improve the productivity of his peers by removing the time-consuming data entry quotient.

In the company blog post, Bellows writes, “Five years ago I felt pain, and I smelled opportunity. The pain I felt was from salespeople struggling to make their number, close that last deal, make club, and reach their goals.”

So, he thought up an idea of an email productivity software that could help solve this issue. And along with his former business partner, Andrus, he brought this business to life in September 2012.

The solution they devised, Yesware, integrates with Gmail, Microsoft Outlook, Office 365, and Salesforce to deliver value-added services such as real-time email tracking and analytics, customizable sales email templates with A/B testing, and personalized email campaigns.

It even has a CRM integration feature which ensures that sales managers are aware of every step of the sales process. Previously, salespeople needed to manually type updates into customer relations systems. But Yesware has automated this process to improve productivity. Bellows believes that salespersons are ‘not paid to do data entry; they’re paid to close deals.’ Therefore, Yesware links email content, meetings and attachments to the company CRM program (such as Salesforce) which gives teams complete and accurate data to guide your sales strategy.

Nate Castro, Head of Global Services Practice at General Assembly, claims that the engagement insights they receive from Yesware have shortened the sales cycle by at least 20%.

Yesware improves the email productivity of the entire team. It delivers actionable data to salespersons on how to engage with prospects while providing managers with a regularly updated and holistic view of the sales pipeline.

Users have access to all this information via the dashboard of their email account, making the service very user-friendly. This enables the team to stay focused on selling without being distracted by the effort needed to learn a new email productivity software.

The company claims to service 10,000+ companies including Zendesk, Groupon, Square, General Assembly, and New Relic.

Journey From Freemium to Paid

Matthew Bellows, Chairman of Yesware

Bellows, an experienced entrepreneur and manager, initially struggled to get seed money for his Yesware dream, even after pitching it to around 45 different investors.

During this period, he already had in place an 80% functional prototype that was Perl-based. But following a conversation with venture capitalists from Foundry Group, in 2011, he recognized that real value was in a product that was easy to use and would help salespeople sell more, by extracting knowledge from their email data. So he trashed the existing prototype and focused efforts on building a simple Gmail plug-in to do the same job more efficiently.

The product strategy revamp worked like magic. In September 2011, Yesware secured $1M in seed funding, from Google Ventures and Foundry Group, among others. This was shortly followed by another $4M raised in April 2012. With this capital, the company hired world-class engineers who then went on to build Yesware’s beta version.

Initially, Yesware offered basic services free of charge while more advanced features came at varying prices ranging from $10 to $1000. This free to download model, released in September 2012, swiftly attracted 120,000+ users. They even got some positive reviews, word-of-mouth referrals and signed on Groupon as a client. But Yesware’s journey from a freemium to paid pricing model was a tumultuous journey.  

By early 2013, even with a growing internal sales team, Yesware was unable to meet its sales targets and had yet to turn a profit. So, raising the next round of funding was also getting difficult. A certified meditation instructor and a true believer in bringing mindfulness into the workplace, Bellows tried to seek out the root cause of the problem by taking a more thoughtful approach.

This is when Bellows realized that he was too close to the problem and had to make some disruptive decisions to turnaround the company’s future. Therefore, he promoted his best salesperson to director of sales and got him to manage the sales-team reboot. He also hired and tasked a V.P. of sales to improve the team’s performance. By June 2014, the company beat its $4,000-per-person monthly sales quota by 163%. And by October that year, they closed a $15M in funding and another $13.3M was raised in June 2015.

Today, Yesware offers a 28-day free trial followed by the option to pick from three rental plans (Pro, Premium and Enterprise). Ranging from $12 to $55 per month, each offers different combinations of software services tailored to fit the needs of busy professionals and data-driven team.

In April 2016, Yesware along with HubSpot Sales, SalesLoft, ToutApp, and ClearSlide were named leaders in G2 Crowd’s Email Tracking Software Grid report, by, for strong customer satisfaction scores and large market presence.

Over the last 18 months, the SaaS brand has grown significantly in revenue. According to a company announcement, Yesware even achieved its first cash flow positive quarter in Q2 2018, while serving 60,000+ active users.

“In the past year, we’ve doubled the size of our product team, our design team, and our support team. We now plan to double the size of our engineering team to deliver on our product vision. I’m excited to assume this new role as we continue to innovate our product in new and diverse ways to improve our customers’ sales productivity,” said Joel Stevenson, on talking on the new role at Yesware, to CNBC.