What is Yesware?

Our Hypothesis

Pressure on salespeople is ever increasing, but the tools that most companies give them are crap. The software that salespeople use, especially Outlook, is not designed for the way they work. The services they use, especially CRM, were designed for management oversight, not sales productivity. Yesware will optimize email and CRM functionality, and add some special sauce, so salespeople can do more deals faster.

Background

Cashman and I started Yesware with the overall goal of improving the professional lives of salespeople. I’ve been in sales for most of my career, both at other peoples’ companies and as the revenue guy for our previous startup, WGR Media. So I know the responsibilities that salespeople feel towards their companies, and the pressures that we are under to make the numbers. If we could help a salesperson do her job better, contribute more to a conversation, keep up with a thread, communicate with just a few more clients, close a few more deals, their business would benefit, they would benefit, and we could build another company.

We are starting with email because it’s the most important communications medium for B2B salespeople right now. People send about 47 billion emails a day (Spambots send the other 200 billion) so even a small improvement in the email experience would make a big difference. We are building stuff that will make more than a small difference in the way salespeople use email. Moreover, although most salespeople hate CRM, there are aspects of it that are essential for their daily work. The two main problems with CRM are:

It’s designed for sales oversight, not revenue generation
It requires a huge amount of time-wasting data entry

Yesware is built from the start to serve the needs of salespeople – to minimize data entry, to automate conversation status and deal tracking, to simplify and standardize reporting, to research prospects proactively, and to inspire greater performance with goal setting mechanisms that work so well in video games.

People say that starting a company is difficult, stressful, hard – and I suppose it is. But we have been inspired and mentored by a lot of great people, with Yesware and our previous company. Building a company is fundamentally a creative process, and being creative at your job is pretty much the best thing anyone could want. We’d love to keep in touch with you. Please add us to your RSS feed, or follow Yesware on Twitter. If you’d like to join the Yesware beta test team, please give us your email here. Thanks for your interest!

All-in-one sales toolkitClose deals faster with Yesware

Yesware FAQs

1. What is Yesware?

Yesware is a sales engagement platform that integrates with Gmail and Outlook. It helps sales professionals track emails, schedule follow-ups, use templates, and gain insights into buyer engagement. The goal is to close deals faster with less manual work.

2. How does Yesware work?

Yesware works inside your inbox, providing email tracking, scheduling, and CRM integration without switching tools. It captures engagement data, automates routine tasks, and surfaces insights that help sales teams stay focused on selling rather than administrative work.

3. What is Yesware used for?

Yesware is used by sales teams to improve communication, track engagement, and streamline workflow. From monitoring who opens emails to sending personalized campaigns at scale, Yesware ensures sellers can prioritize the right leads and close deals more efficiently.

4. Do I need Yesware if I already have a CRM?

Yes. CRMs are great for record-keeping, but they aren’t designed for daily sales outreach. Yesware integrates with leading CRMs, automatically logging activity and eliminating manual data entry, so sales reps save time while keeping pipelines accurate.

5. How does Yesware help with email tracking?

Yesware provides real-time notifications when emails are opened, links are clicked, or attachments are viewed. This allows sales teams to follow up at the right moment, prioritize engaged prospects, and make data-driven decisions on how to move deals forward.

6. Can Yesware help me write better emails?

Yesware offers customizable email templates, mail merge campaigns, and engagement analytics to optimize messaging. Sales reps can test which emails perform best, share winning templates with teammates, and ensure every message is tailored yet efficient.

7. What makes Yesware different from other sales tools?

Unlike traditional CRM or email add-ons, Yesware is built for salespeople first. It combines email tracking, templates, reporting, and pipeline insights directly in Gmail or Outlook, reducing tool fatigue and giving sellers everything they need in one place.

8. Is Yesware easy to use for small sales teams?

Yes. Yesware is designed for individuals, SMBs, and enterprise teams alike. Setup is simple, and features like shared templates, reporting dashboards, and automated tracking scale with your team as you grow, without requiring heavy onboarding or IT resources.

9. How does Yesware integrate with Outlook and Gmail?

Yesware integrates seamlessly with both Outlook and Gmail, embedding its tools directly into the inbox. Users can track opens, schedule emails, and log activity to CRM without leaving their preferred email environment, making adoption frictionless.

10. Can Yesware improve my sales team’s productivity?

Yes. By eliminating repetitive tasks like manual logging and providing data-driven insights, Yesware frees up salespeople to spend more time selling. Teams report higher response rates, better pipeline visibility, and faster deal cycles using Yesware.

11. Does Yesware replace my CRM?

No, Yesware complements your CRM. It automates data entry, syncs activity, and provides insights into email engagement that most CRMs can’t capture. This ensures your CRM is accurate while empowering sales reps with actionable information in their inbox.

12. Who uses Yesware?

Yesware is used by sales reps, managers, and revenue teams across industries—from startups to Fortune 500 companies. It’s particularly valuable for teams that rely on email outreach and want to improve efficiency, engagement, and deal outcomes.