Chapter 8
Outbound E-Mailing and Messaging
This is a long but incredibly important chapter.
To recap where we are at this point in the sales process:
- You have your list of target companies.
- You cleaned them for duplicates.
- You know whom you want to reach at the companies.
- You have their contact information.
- You did your research.
- You have the lists properly segmented.
Now you'll learn:
- What types of messaging are effective in getting positive responses
- A/B testing and e-mail optimization
- What metrics to measure and how to use that information to take action
- How to set up a cadence and how often and for how long you should send e-mails
- The top tools in the B2B Sales space and how to use them
- How to turn negative responses into positive responses
You're ready to start activating your prospects, but before you send anything, you need to focus on your message. There are a lot of resources available that show you how to write cold e-mails.
For subject lines, check out fun and insightful articles from Copyblogger, HubSpot, Buffer, and Quick Sprout.
For the body of the e-mail, I recommend that you check out The Boron Letters and Neville Medhora for AIDA copywriting help. See SalesFolk.com and BreakthroughEmail.com for help on writing cold e-mails.
Additional suggested reading in the resources appear in “Resources and Programs” at the end of this book. For now, I am going to focus on the topic of outbound e-mailing. Check out the resources suggested above for sample e-mails.
The tools used for sales automation have changed the game for those who embrace science in sales. You can track, measure, and optimize like never before. You can see when, where, and how long someone is reading your e-mail. If you have a link or a presentation, that can also be tracked. The level of visibility you can get these days is incredible. However, what really matters is what you decide to do with this information.
A/B Testing and Optimizing E-mails
Before you create your campaign, it's best to understand the process. You'll want to test a few things:
- Opened or viewed rate—this is the strength of your subject line
- Click-through rate—this is the strength of your call-to-action
- Response rate—this is the strength of your message
- For response rates, I usually only count positive or lukewarm responses. Negative responses like “take me off your list” don't count, but they should be read for feedback purposes.
The best way to optimize for each of these is to A/B or multivariable test your e-mails and send them through one of the e-mail campaign tools so that you can get accurate metrics. The previous segmenting we did earlier was also helpful for the following reasons:
- Segmenting and results based on segmenting help you measure and optimize e-mail campaigns. Sometimes you'll just have a low-performing segment or list for one reason or another.
- It's easier to send batches of e-mails. I recommend sending 50–100 e-mails per day, per single e-mail address. When you send fewer than 50 e-mails, your sample size is too small and you're going too slowly. When you send more than 100 e-mails, you start to trigger spam filters in Gmail.
- Smaller lists allow you to personalize to your audience based on buyer persona. So, if your list is a vice president of marketing in a company that is based in Boston and is in the health care industry, you can tailor the message to that buyer persona and hit the entire list at once with a much more personalized message.
The first thing to start with is the subject line. Take a subset of your lists, at least 50–100 e-mails per test, and start sending the same e-mail, but with different subject lines. Do this four times. Then take the e-mail with the highest open rate, and use that one as the baseline in a new test with three other subject lines.
The appropriate person or introduction request subject lines from earlier in the book are my baseline e-mails to test against. These subject lines have been shared across the Internet, so I'm surprised they still work, but they still do, somehow. The goal is to get open rates at a minimum of 30 percent.
Keep testing until you get there, but don't stoop to low levels just to get high open rates. Using an artificial forward or reply is a way to trick someone, and the person will know that. If you play tricks, you'll abuse your prospects' trust before you ever get a chance to open a dialogue, and that's not going to bode well for you.
One thing to test is using the person's name or the company name in the subject lines. This makes the e-mail look more personal before the recipient even opens it.
Next, test different locations and languages for your call-to-action, using either links or attachments. Try to make sure your e-mails look like casual e-mails and not marketing e-mails when you do this.
Lastly, the body of the message should be short and to the point. Don't give too much information. Provide value for the recipients, feel their pain, talk about them—not yourself. If you have done your research and you are reaching out individually instead of mass e-mailing, then you should know what their initial problems might be.
Always go into this opening e-mail campaign with the goal of setting up the first call. Do not aim too high or ask for too much. Be strong, and lay out a certain time to speak. Don't ask.
Even though you are collecting information on open, click-through, and response rates, the only thing that you need to worry about in your pipeline is the number of meetings that you set up. You are using all of these e-mail metrics to make your e-mails better so that you can set up more meetings.
The numbers will vary by whom you ask and the type of business, but you'll want to aim for numbers like the following:
- Open rate: 30–50 percent
- Click-through rate: 20–35 percent
- Response rate: 15–30 percent
- Meeting set-up rate: 10–20 percent
There are many other variables at play here that could lead to skewed numbers. Some of these variables are the following:
- Poor performing lists
- Server or sending issues
- The sales rep who is sending the e-mails
- Time of day and/or the date
To counteract some of these variables, do research. According to the sales automation company Yesware, your e-mail has a very low chance of being opened if it hasn't been read within the first 24 hours.
Many experts advise sending e-mails at 9:00 AM local time on Tuesday and Wednesday. Some like to send e-mails from 3:00 to 6:00 PM local time on Tuesday and Wednesday to catch people as they're getting out of work. Others say that sending e-mails on weekends is best, since people don't get a lot of e-mails then, so yours will stand out more.
There are many different studies and justifications for timing e-mail campaigns. I recommend that you take advice from a few sources and see what works best for your audience. Again, you can always lean on your allies. Don't be afraid to ask what works for people in your product's space who aren't competitors. Save yourself some time.
Figure 8.1 Test, Measure, Optimize
Determining Your Perfect Cadence
Outbound sales campaigns also go by cadences or sequences and are run through e-mail automation software. A cadence is considered your outbound messaging rhythm in which you mix in various types of contacting, such as through e-mail, social media, and the phone, over a set period of time. Maybe you call on day 1, e-mail on day 2, and call and e-mail on day 5. This is a sample of a cadence that you can create for contacting potential buyers.
I'll go over the tools for doing this shortly, but, first, here are some high-level strategies to understand.
When you are setting up outbound sales campaigns, you'll need to pick a number of touches per lead and decide how to contact them.
Recently, HubSpot ran a study that said that, after nine touches, you've reached the point of diminishing returns. In the advertising world, they say that customers need to see your brand seven times before they can start to recognize it.
Tawheed Kader, the chief executive officer (CEO) at ToutApp, calls his cadence the “five by five” (five contacts, or touches, over five days). Kyle Porter, the CEO of SalesLoft, calls his cadence the “seven by seven” (seven contacts, or touches, over seven days).
According to Kevin Gaither, vice president (VP) of inside sales at ZipRecruiter,
Most outbound reps give up after one to three attempts to a lead, but statistics from www.InsideSales.com and Velocify show that you'll need six to nine touches to establish contact and qualify the lead. Once you've made your six to nine touches over a three-week period, only then should you put your lead into a Nurture Queue for follow up at a later date.
John Barrows, one of the leading sales trainers and sales development rep (SDR) trainers for Salesforce, Marketo, LinkedIn, Box, Zendesk, and others, says you should keep contacting potential customers until they give you a response or a definitive “no.” Then he recommends following up again in a few months.
I tend to agree with John. I think the best salespeople are very persistent. In sales, “no” is the second-best answer. “Yes” is the first, but a “maybe” or not receiving an answer at all are by far the worst. This seems to be something nobody in sales can agree on, but I think it's something that should be different for every business. It depends on deal size, pipeline, number of leads and active leads, and other factors. This is where you can play around and see what's best for you.
Here's where segmenting comes into play again. You'll have maybe two or three groupings of leads. The top group, your whales or low-hanging fruit Fortune 500 companies, would get phone calls built into your campaign. The next group would only get e-mails, but with a high personal touch (meaning, deeply segmented, or somewhat customized). The bottom group would get a standard outbound drip campaign from the salesperson until they responded.
I don't like calling everyone, but some salespeople do. I think you need to have extra resources for that to work well. If you're an individual sales rep with a territory at a big company, go ahead and call everyone. But if you're a cofounder or an early stage sales hire, you're probably spread too thin to call every single outbound lead.
I also don't like stopping a cadence, but some salespeople do. Only when people reply do they get taken off the list. If it's a hard “no,” you can reach out again in six to nine months to see if the timing is better. As the campaign goes on, time between e-mails should lengthen to a maximum of two weeks. Basically, if you're hitting the right person with the right message at the right time, you shouldn't stop until you have a hard “no.” The sales industry experts have very different opinions about this, but it depends on your company, process, value proposition, and personnel. I like to call the best leads first and then send e-mails to the less important leads until I set up a warm call.
The Services That Power Outbound Sales
Companies offering services that power outbound sales are my favorite because of how useful they are. Each one of these companies has the potential to be a billion-dollar company and the best friend of salespeople everywhere.
Users can build and optimize e-mail templates, and A/B test, track, and send e-mails to groups of prospects all at once. Some of the companies have much deeper analytics for managers, which we won't discuss very much in this book. Many integrate with Salesforce, Gmail, Outlook, and other customer relationship management (CRM) systems, so they should be able to handle whatever systems your company is built on.
The following tools are being used across organizations, not just in sales.
Cadence (from SalesLoft)
I went over SalesLoft's prospecting and lead-generating tool in Chapter 5, but recently SalesLoft has released a new product that allows you to take those leads and start prospecting. Its tool is built directly for both the outbound and inbound SDR, and helps them not only with e-mail contacting but also with phone contacting. For example, you can set up and run a campaign inside of Cadence that consists of e-mails and phone calls that looks like this:
- Day 1: E-mail.
- Day 2: Call in the morning.
- Day 3: Call in the morning without voicemail; call in the afternoon with voicemail.
Featured Use Case Study
Insightpool has dedicated its entire outbound sales process to the Cadence tool. Cadence is the application of record for the SDR team, helping the team create, maintain, and improve on the phone call and e-mail process. The system gives the sales reps a simple process to follow for creating e-mail templates, tracking and analytics, power phone call dialing with voice recording, notes storage, and syncing with a CRM system.
Check out SalesLoft's Top Secret SDR Playbook for guidance on setting up your Cadence.
Outreach.io
Outreach.io is a really strong new player in the outbound sales space, with a solid team and a sturdy product. The key difference between Cadence and Outreach.io is that, instead of firing a pixel, like all other e-mail tracking software companies, Outreach.io hooks into your SMTP (Simple Mail Transfer Protocol) server. RelateIQ did this in the CRM space and found that this gives you better and more accurate data on your replied rates. RelateIQ is also fairly intuitive. It filters out duplicate e-mails automatically and gives you recommendations on the best times to send your e-mails and how many e-mails to send.
Featured Use Case Study
The sales team at Datanyze was looking to automate cold outbound outreach and put it on cruise control. The sales team wanted to create a series of touchpoints that would stop upon a reply from a prospective customer.
The sales team at Datanyze had two requirements:
- Reply detection had to be bulletproof. Datanyze could not afford an e-mail going out to a prospect who had already engaged with sales.
- They needed to be able to easily A/B test their e-mails and change things on the fly. The sales team was extremely metrics driven and wanted to use testing as a way to improve conversion from current leads.
Since using Outreach.io for outbound sales, Datanyze has hit 50 percent reply rates for cold e-mails—a number that previously had been impossible to achieve.
Outreach.io also serves as the midfunnel sales touchpoint for inbound teams. SDR and marketing development rep (MDR) teams have the ability to reply to inbound leads with one-to-one personalized sales e-mails coming directly from the sales rep based on lead attributes.
Outreach.io integrates with Salesforce, Outlook, and Gmail.
ToutApp
ToutApp is designed to help sales and business development professionals manage, track, and gain insights from their e-mails. Over the last three years, ToutApp has been able to develop a very robust and invaluable sales tool that is now being used across entire organizations. ToutApp built an incredible team out of San Francisco that has done an amazing job in growing sales reps who have had little previous experience. Without much funding and only one full-time developer, ToutApp has come a long, long way.
Some of the more advanced features of ToutApp are the following:
- A live feed, so users can see in real time when an e-mail recipient opens the e-mail, clicks on a link, or opens an attachment, as well as what page of the attachment the recipient has read and what page of the user's website the recipient is viewing.
- Group e-mails that can easily be searched for all those who haven't responded so that a follow-up message can be sent to them.
- Visual tracking of prospects' engagement through their views, clicks, and replies.
- Scrapes contact information from any website and ensures that ToutApp and Salesforce are always up to date.
ToutApp plugs directly into both Gmail and Outlook, and it has a deep integration with Salesforce, so sales reps and managers can access ToutApp data and tools from anywhere they like. ToutApp also integrates with marketing automation platforms like Marketo so that sales and marketing reps can stay in sync and see what messaging is resonating the best with prospects to move them through the pipeline.
Featured Use Case Studies
By tracking with ToutApp, a director of hospitality sales at an NBA franchise was able to close two six-figure deals in one month, which he wouldn't have been able to close otherwise. With the first deal, he was able to see his e-mail being forwarded to multiple people at the prospective company and that the recipients were actively engaged and interested, so he gave them time to continue gathering information, and then he followed up at the right time.
With another prospect, the director was having a hard time getting in touch with someone whom he already knew would be interested in purchasing a suite. The prospect went dark, and there was no contact for several months, until the prospect popped up on the director's live feed one day. The director called the prospect while the prospect was looking at his e-mail and closed the deal on the same call.
Yesware
Yesware is an e-mail productivity service for salespeople and is another one of the major companies in the outbound sales space. It has only been around for a few short years but has created a great product for today's salesperson. Yesware has double the head count of ToutApp and has raised four times as much money. It is based in Boston and now has offices in San Francisco as well.
Some of the more advanced features of Yesware are the following:
- Yesware Mobile allows sales reps to send and track e-mails and to access e-mail templates through their mobile device. Activity is automatically synced with Salesforce data.
- Swipe-to-call allows a sales rep to call a prospect directly from an e-mail thread. Yesware's data shows that responding to a recently opened e-mail results in a 30 percent higher connection rate. This tool allows a salesperson to quickly reach out once an e-mail event takes place, even while the sales rep is on the go.
- Yesware's presentation tracking feature gives deep insight into how engaged a prospect is with any content that is being shared. Sales teams are able to see how many people were sent the presentation, how many views the presentation received, and the average time recipients spent viewing the presentation.
Significant use yields larger amounts of collected data, which builds a more complete picture for sales reps and managers when they are analyzing individual performance, team performance, best practices, progress over time, and so forth. In addition, Yesware provides actionable insights. For example, Yesware's data shows that Monday is not the best day to send an e-mail. The highest number of opened e-mails occurs on weekends.
Featured Use Case Study
Acquia took advantage of the e-mail-tracking feature in Yesware to collect data around various events, like e-mail opens, link clicks, and attachment views. This information allowed Acquia to take a great deal of the guesswork out of the sales process, resulting in fewer touches to move a deal through the pipeline. The information also made it easier for sales reps at Acquia to prioritize prospects and determine their next steps, including when they should call.
Sales reps who called a prospect immediately after the prospect opened an e-mail, clicked a link, or opened an attachment connected with that prospect over 34 percent of the time. Overall, Acquia's use of Yesware data to determine who and when to call improved the sales reps' overall call connection rate by 29 percent.
SalesforceIQ
In 2014, Salesforce acquired RelateIQ for a whopping $390 million, but the service just released and became a lot better. SalesforceIQ integrates very well with other services you're using, without the need for an external integration tool. The best integration is via your e-mail's SMTP server, similar to Outreach.io, and of course, to Salesforce. This allows SalesforceIQ to pull in information from your e-mail and calendar and to give you a clearer look at your data for each lead.
SalesforceIQ's filtering and its Gmail extension are probably its strongest assets. It's nice when you can use a CRM tool from Gmail without having to open new tabs. The CRM filtering was built in an intuitive way that allows you to sift through data both accurately and easily.
Cirrus Insight
Cirrus Insight is a plug-in for Gmail and Outlook that automatically updates Salesforce as you work. Some of my favorite features include the ability to track e-mail opens, to share available meeting times, to merge e-mail templates, and to sync e-mails and calendar events with Salesforce. The best part about it is that it allows sales reps to stay in one screen without the need to click around and get bogged down in tedious data entry tasks.
PersistIQ
PersistIQ is an outbound sales platform—an interesting up-and-comer in the SDR space. The product is well built, with key features such as the ability to de-duplicate e-mails and to show your previous conversations with a lead from Salesforce. The product is very similar to Outreach.io and Cadence.
Pouyan Selehi, CEO of PersistIQ, says that he built PersistIQ because:
We think reps should focus on the quality of your outbound sales instead of just quantity. This means take the time to think through and create prospect profiles and create targeted messages. Try different messages, wait different periods of time between touchpoints, and segment differently. Find what works for you.
LiveHive
LiveHive adds a bit of prediction on top of the e-mail automation process. With LiveHive, you get e-mail opens, link clicks, document downloads, page-by-page analytics, and can see the time you spend on each page of sales collateral. LiveHive then analyzes these behaviors to help prescribe the best course of action based on past results. The feature SmartPath allows you to set up e-mail sequences and add and remove leads on the fly.
Sidekick (from HubSpot)
HubSpot's Sidekick is a little different from the other Enterprise Players. HubSpot's claim to fame is that its product is made more for the sales rep than for the manager.
Brian Balfour, who leads growth for Sidekick at HubSpot, explains:
Sales reps need tools that make their day faster, more productive, and more efficient. We developed a tool with the sales rep in mind, growing adoption through the frontline sellers, and learning what their specific needs are.
Sidekick has an activity feed for sales reps so they can be notified about actions in real time. Obviously, Sidekick has deep integrations in HubSpot's marketing and CRM software, as well as in Salesforce. If you're already heavily reliant on HubSpot, this might be a good option for you.
A unique integration that I like is Sidekick's connection with Zapier. Sidekick syncs with the various tools and apps that are available through the Zapier app exchange. For example, sales reps can sync with Twitter and Sidekick to get customized tweet notifications in their Activity Stream, and Sidekick also syncs with Zendesk to get support case information.
Sales and Customer Success
The following tools were built for the sales organization, more specifically, SDR teams.
Sendbloom
Sendbloom is a sales-driven sales automation platform in the SDR space. Its goal is to allow you to more deeply segment your lists and to engage with the prospects at scale. Sendbloom's system actually builds in more data about your leads for you and then helps you figure out how to segment your lists and craft messages that will create action in that specific segment.
Sendbloom helps sales and marketing development teams nurture target accounts and stay on top of inbound leads. SDR teams need to know that there is no one-size-fits-all message. With Sendbloom, SDR teams can create conditional segments for their leads based on criteria like the prospect's title and analytics stack. The product is doing this research for them programmatically, and only the prospects that don't reply receive another message.
For testing how e-mails will look on different devices and on e-mail clients' servers and browsers, check out E-mail on Acid and Litmus.
Quick Tips on Messaging Psychology
Consider the following tips in order to communicate clearly and build rapport with your target customers through your outreach.
1. Pay Close Attention to the Words You Use
Think about this for a second. If we're partnering on a project, and I tell you that you're going to have a lot of responsibility, you'll see that as daunting and stressful. If I tell you that you'll have a lot of control, you'll see that as freeing, and you might be enthusiastic. They both mean the same thing, but because of the wording, each comes across differently to the other person.
There's a big difference in someone's mind when you use the word contract versus the word agreement. But often they mean the same thing.
When I left Udemy, I wrote messages to people in my personal network, asking them to introduce me to companies that needed a business development lead. I knew I wanted to stay at a small start-up, but I wanted to explore all of my options, and I didn't want to consider offers while I was still with Udemy.
One thing to know and never forget: it's not what you ask that's important; it's how you ask it. Instead of saying, “I just left my company. Do you know anyone who is hiring?” say, “I just left my company. If you know anyone looking for a skilled business development person, do them a favor and introduce them to me.” It completely flips the script. Whether it is written or relayed in verbal communication, a lot can be achieved in how you phrase things.
2. Keep It Short, and Dumb It Down
Nobody wants to hear your jargon- and abbreviation-riddled, multiparagraph sales pitch. Even worse are salespeople who use big words to sound smarter or more knowledgeable. In the end, you will lose potential customers because you're not making it easy enough on them.
Keep communication easily readable for your recipients so that they can digest the information quickly and take action. Imagine that your recipients are reading your message on their smartphone on a bus ride home after a long day at the office. You'll want to make sure that your message is short and easy to read. That's the only way they'll read it all the way through and take action.
Be sure to make the key points and preferred actions clear; you may even want to highlight them in bold.
Instead of using the word utilize, choose the simpler word use.
Don't use abbreviations unless they're universally well known in the industry, like CRM or ROI (return on investment). Acronyms such as Customer Life Time Value (CLTV), Customer Acquisition Cost (CAC), and Average Revenue Per Account (ARPA) are not used universally. Stay away from using words, phrases, and acronyms that the recipient may not understand.
Don't be afraid to go against the principles of writing in your e-mails. This isn't your high school honors English class; this is an important message to a busy potential buyer. Try adding more spacing in your e-mails—separate paragraphs every two sentences. Make it easy for readers to scan or read your e-mails quickly.
Make your message simple enough for an eight-year-old to understand.
3. Don't Be Afraid to Challenge People
When you are setting up an outbound messaging campaign or to make sales in general, you'll need to have a thick skin and sometimes a short memory. There will always be people with a poor attitude who reply to your messages. Just keep pushing, but do it the right way. You're just doing your job, and know that for every 1 person who responds negatively, you'll sign up 50 more.
Don't ignore the negative people, either. Sometimes a great way to reply is by challenging them.
At Udemy, we would sometimes get poor replies from experts. As we refined our sales process, we received fewer and fewer negative replies, but it still happened once in a while. If we read the situation well and knew a little bit about the recipients' background, sometimes we could flip them. Sometimes I would respond with a challenge. I would find two big-name experts in their space whom they knew, and I would reply in the following manner:
Hi [First name],
Sorry to have bothered you. I thought you were on the level of [expert 1] and [expert 2] who are both doing extremely well on Udemy. That's why I thought this would be perfect for you, but I guess I was mistaken.
I will make sure you do not receive another e-mail from us.
Again, I apologize.
Best,
Max
In this case, you're challenging them by saying that if they do not see the value of your service, they must not be such a big-name expert. Some people will call your bluff and not respond; others will respond with a simple “thanks.” But sometimes, and more often than not, you'll get a response such as, “Oh I didn't know [expert 1] and [expert 2] were at Udemy. Maybe I will have a few minutes to chat this week.”
4. Sell to the Individual, Then the Employee, Then the Company
The people on the other end of your messages are individuals, first and foremost—human beings with feelings, emotions, wants, and needs. Appeal to them as individuals first, making them feel like they'll be more special or important if they listen to you. Then appeal to their career goals, and explain how using your company's services will make them look good to their boss. Lastly, appeal to them by providing the tools they will need to sell the rest of the company on your product. For example, describe how using your services will make them look like a hero to their team and how their team will become more productive and generate more revenue—tell them how to sell your services to the key stakeholders.
Here are a few more things to note when you are conveying a message via e-mail, from cold e-mail expert and CEO of Salesfolk, Heather R. Morgan:
- Make your e-mail conversational and human. Don't write like a robot or be gimmicky like a marketer.
- Be persuasive. Try to evoke emotions.
- Talk about your product or service in terms of benefits instead of features. For example, say, “Use this process to triple your response rates” instead of “This feature helps with A/B testing to write better e-mail copy.”
- It's more convincing to show the benefits of using your services in the form of a case study sentence rather than simply telling them. Use a statistic, if possible. For example, say, “Our e-mail copy helped [Client] double their qualified leads in a month, which also doubled their sales team's quota.”
- Try to add value, evoke fear of loss, or play on people's competitive nature.
- Be focused, and don't try to cover too many tangential points in one e-mail.
- Develop a clear persona for each segment list.
- Introduce only one concept or idea per e-mail. If you have a lot of value propositions and ideas, relax, and save them for other touches in your campaign.
- Send six to eight e-mails for every person you're reaching out to.
- In some cases, you may actually get more responses by sending six to eight e-mails than any other touch point earlier in your campaign. Even if this isn't the case, it's still worth it to get the people who respond on e-mail six to eight that would have otherwise stayed cold.
- Test everything. Every persona and industry is different, so you need to test things to find out what works.
- Stay away from long sentences or long paragraphs.
- Don't be afraid to ask for things or demand things; just do it politely.
- The difference between being pushy and persistent is politeness.
- Try putting the company name in the subject line.
Visit www.SalesHacker.com/library for more guidance on cold outreach and outbound e-mail messaging campaigns.