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Email Secrets of the Sales All Stars

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As vital as email is, it can be difficult for salespeople to compete against the sheer number of messages that their prospects and customers receive. How do you know what’s working and what’s just a …

As vital as email is, it can be difficult for salespeople to compete against the sheer number of messages that their prospects and customers receive. How do you know what’s working and what’s just a waste of time? Drawing from recent Yesware data of more than 6,000 salespeople and 22M+ emails, this decks offers all new insights on how email habits impact sales performance. Learn how to increase your reply rates and ensure your emails are being read.

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  • This is me when I started Yesware with my CTO Cashman Andrus. I was younger, thinner and better looking. I was VP of Sales at a venture backed startup. I had been in sales for my whole career, with my own startup and while working for others. I was continually frustrated at my team’s productivity, and my inability to understand what they were doing. The 48 hours before a board meeting were the worst days of my life.
    Just like millions of other salespeople, we were using generic tools like email, calendars, spreadsheets and phones for a very specific, high value activity. CRM systems, which were suppose to help me understand what was going on, were plagued with the same old “garbage in, garbage out” problem we see so often with business systems.
    WIIFY – You know I’ve personally experienced this problem both as a salesperson and a sales manager.
  • We started by building a great free product. The freemium distribution approach is perfect for salespeople, because they aren’t interested in technology. But they are keenly interested in performance, success, and the social credibility that comes from sharing a great service with friends and colleagues.
  • As a salesperson uses Yesware, they create a stream of data about them, their prospect and their deal. This can be aggregated into manager reports and your CRM.
    So a manager can use Yesware to see who is working out, what’s happening with each deal. To get their team up and running faster, measure activity and share what’s working.
  • Open Rates:
    15 days between 12/8 and 12/23
    Recipients in 132 countries
    79,989 emails sent in total / 19,146 opened
    Looked at both averages and outlier performers
    Gmail/Chrome users – maybe atypical
  • This data doesn’t have the “don’t know don’t know” problem that the Open Rate data does.


  • 1. Email Secrets of Sales All Stars Matthew Bellows
  • 2. 2
  • 3. It’s MOVEMBER! mobro.co/matthewbellows
  • 4. Yesware for Gmail 4
  • 5. Yesware/Salesforce Sidebar Speeds Account Updates Instant Deployment Displays Account, Asset, Campaign, Case, Contract, Opportunity, Product, Solution, Task, Event, Contact, Lead Even if they’ve been customized Plus any custom object
  • 6. User Data Aggregated for Enterprise 6
  • 7. Yesware Market Position Prospect ExactTarget, Marketo, Hubspot SAP, Salesforce.com, SugarCRM, Dynamics. Qualification & Nurture Opportunity Tracking Deal Closing New Customer 7
  • 8. Total Users: 3x Growth this year Revenue: 17x year over year
  • 9. Recent Notable Deals
  • 10. Impact of Inside Sales at Yesware
  • 11. Data Collection Methodology Three Studies: Open rates: Open rates pulled anonymously from 6,000+ salespeople that use Yesware All Reply Rates: From August 2011 - August 2013 22,743,966 sent, 7,916,979 replied Benchmark: Same date range, one leading inside sales company - 1,090,464 sent, 423,765 replied Sprinkled Throughout: Tips and Sample Email Templates
  • 12. Overall – 23.9% Sales Email Open Rate • 24% underreports opens: no image load = no data • But we know a lot about that 24% (n=19,146 emails)
  • 13. Overall Reply Rate: 35%
  • 14. Getting Another Name Bumps Opens Opened email audiences Send to three if you can • Sending to 2+ increases your chance of opening • “Is there someone you want me to copy on this?”
  • 15. More Names = Higher Reply Rate
  • 16. Example: Mention Other Stakeholders Mention other stakeholders. Emails have higher open rates when sent to multiple people and get higher response rates when mentioning other stakeholders at the company. Subject: Get 100% Salesforce Compliance with Yesware [Jerry and Rahul], [Ali told me he's interested in getting Yesware for the sales team but that the XXX acquisition may stall conversations.] Customers like GoodData and Adroll told us that too often data in Salesforce is inaccurate and they need more transparency into their pipeline. That's why they chose Yesware to sync email and calendar activities automatically and build SFDC reports specific to their needs. Are you available [Friday at 10am] EST to discuss how Yesware can help the [XXX] sales team be more productive? currently at 33% reply rate
  • 17. Highest Open Rates on the Weekend Send your most important emails on Friday afternoon
  • 18. But Your Open Rate Mileage May Vary Track individual rates for benchmarking & performance
  • 19. Reply Rates Steady Thru Week Lower weekend sending volume not justified
  • 20. Opened by Time Since Sent Don’t waste days waiting for a reply…
  • 21. Same Story, Longer Timeframe ‘cause if the email doesn’t get opened soon, it’s done.
  • 22. Replies = Same Story. GIVE UP!
  • 23. Using Reminders For Contact Channel Reminders with No Message Activity Makes more sense to pick a different channel to reach out because the message I sent wasn't engaging enough to get them to open or click. Reminders: Opened or Link Clicked This reminder tells me they might be interested but maybe didn't have the time to respond. For the second reach out, I can send another email but target my messaging more about priority or a particular Yesware feature, especially if they clicked on a link about a particular Yesware feature.
  • 24. It’s a 24 hour Day for Business Email
  • 25. Example: Time Emails for Readers Think about the times when executives take time to read incoming emails. •Early (7:30 or 8am before meetings starts) •Late (after 5:30pm when meetings have ended) •Lunch •55-05 (This means, 5 minutes before the top of the hour, and 5 minutes after the top of the hour... when executives are likely to be at their desks in between meetings) I find this time is actually the best time to CALL if your cold calling in addition to sending emails :-)
  • 26. Yesware’s Send Later Feature Helps Compose a message now Send it when your prospect is likely to open it
  • 27. Shorter Subject Lines = More Opens
  • 28. Example Subject Lines The best subject lines should contain a powerful call-to-action. If you are emailing someone, you are indirectly asking for a their time - it's a commitment. Keep your subject lines to 20 characters or so as many recipients will be reading from a mobile device. Here are a few examples: •Yesware and XXX •10 mins on 11/3? •Schedule time to talk? •You're on my priority list •Drinks at Unconference?
  • 29. Example: In Person Meeting Request In person meetings have higher reply rates. If you're having trouble getting to a prospect ask for an in person meeting with yourself of one of your bosses. Even if they can't actually meet in person you have a better chance of getting a reply and finding a time that works. Subject: Can I come by the office next week? Hey [name]! I'll be in [San Francisco] next week meeting with customers and would love to visit your office too. There are already [x] Yesware users at [company] relying on Yesware to see who's reading their emails. I'd love to show you how you could also take advantage of features like team templates and our Salesforce integration with Gmail. Are you available [Tuesday afternoon or Wednesday] for me to come by your office? If not please let me know when works for a quick call. currently at 41% reply rate
  • 30. A Little ‘Humor’ Is Ok… Hey Tim, I haven’t heard back from you and that tells me one of three things: 1)You’ve already chosen a different company for this, and if that’s the case please let me know so I can stop bothering you. 2)You’re still interested but haven’t had the time to get back to me yet. 3)You’ve fallen and can’t get up – in that case let me know and I’ll call 911 Please let me know which one it is because I’m starting to worry… Thanks in advance and looking forward to hearing from you. Cheers, currently at 46% reply rate
  • 31. Example: Always End with CTA Make it a point to end every email with a pointed call to action. i.e. Buy or not buy? Meet or not meet? Interested or hold off? Subject: [x] messages not synced to Salesforce? [Karen], There are [47] Yesware users at [XXX] who last month sent [9370] emails and tracked [6034] with an average reply rate of [40]% and open rate of [67]%. We last left off discussing how we could implement Yesware Enterprise so all their email/ calendar activity is automatically logged in Salesforce and so you could share the dozens of templates they're already creating. Are you available to evaluate Yesware for your team [Monday at 2pm] EST? If not please let me know when's best. currently at 52% reply rate
  • 32. 5 Tips for Your Sales Emails 1. Sending to 2+ increases opens and replies • “Is there someone you want me to copy on this?” 2. Send emails on Friday afternoon • Weekend open rates are highest 3. But don’t wait days for a reply • After 24 hours, your email is all but done 4. Email reading happens 24x7 • Schedule your sends for very early in the morning
  • 33. 4 More Tips for Your Sales Emails 1. Track individual rates for benchmarking • Open rates vary widely by reps 2. Company name in your subject lines • Several leading openers do this 3. Shorter Subject Lines are Better • >3 words = below average opens 4. Promise to Add Value • “Free Boot Camp Marketing Ideas”
  • 34. please contact: Matthew Bellows matthew@yesware.com 617 331 0240