How to Automate Email Prospecting Without Losing Your Soul

How to Automate Email Prospecting Without Losing Your Soul

In this post, I will walk you through how to shorten your sales cycles effectively, nurture leads better, and generate more conversions for your business.

When thinking about the work that salespeople do, many imagine the Mad Men era when representatives would go to clubs or make a phone call to introduce themselves to a prospect. 

But as you know from experience, that's not the reality anymore. You don't just spend your days sweet-talking to potential clients until they shake your hand and give you their account. In fact, the average salesperson spends less than 15% of their time selling and engaging with customers. The rest is dedicated to manual, repetitive, and (sometimes) boring administrative-style tasks like prospecting. 

Thankfully, you can save yourself the trouble of manually sending hundreds of emails or following up with each prospect by automating your prospecting process.

This post will walk you through how to shorten your sales cycles effectively, nurture leads better, and generate more conversions for your business.

Email prospecting automation benefits

Prospecting is the fuel that keeps your sales process burning. When you find, qualify, and target the right prospects with your message, you increase your chances of turning them into sales-ready leads and growing your revenue.

You want to ensure you send out high-quality emails to capture your prospect's attention while leaving an adequate amount of time between messages to avoid coming across as pushy and annoying. You also need to switch up the content of your emails, so you're not repeating the same message repeatedly.

This might not seem like much work if you only pursue one or two prospects simultaneously. However, when you're juggling multiple prospects, email prospecting can be an immensely time-consuming task.

It can take away from the time you should be spending on other important activities like engaging leads and customers, building relationships, quantifying opportunities, and developing and proposing specific solutions for their needs.


Source: Intercom

This is where email prospecting automation proves valuable. It helps you save time and increase productivity — which means more money for your business. According to Hubspot's 2021 Sales Enablement Report, 61% of businesses leveraging automation exceeded their revenue targets in 2020.

Other advantages of automating your email prospecting process include:

1. Better motivated sales reps

You hired your salespeople because you wanted to leverage creativity and intelligence to sell to customers and boost your company's revenue.

But with all the energy and time they will expend on crafting and sending email messages, then following up with prospects, they might lose interest in the best part of their job: having interesting and persuasive conversations with prospects. Automating the process can boost morale by allowing salespeople to focus on selling.

2. Scalable marketing strategies

With manual email prospecting, there's a limit to how many people your business' sales team can reach and sell to. This means you won't be able to keep up with servicing your prospects and leads if the number increases beyond that limit. 

You can integrate email marketing with other digital tools and track touchpoints with sales automation. This way, every time someone performs a set action, your platform will send them a corresponding message without needing a salesperson to intervene or use up any additional resources.

3. Personalized customer experiences

72% of customers only engage with personalized messaging, and 90% find personalized content to be very or somewhat appealing. Automating your emails can positively impact your ecommerce marketing or lead to nurturing efforts and building stronger relationships with prospects by targeting and appealing to their specific traits, needs, and interests.

4. Refined lead flow and qualification

By automating certain touchpoints and creating predetermined workflows triggered by a set of actions, your emails can double as a screening tool, making it easier for you to qualify leads and move them through your pipeline without resistance.

Automation + email prospecting: how to do it step-by-step

So how do you take the stress of email prospecting off your shoulders with the help of automation? It's not rocket science; you must know and implement the right formulas to get your automated prospecting system up and running effectively.

Step 1. Select automation software

The first thing you need to do is create a strong foundation for your automated prospecting activities, so it's important to select an email automation tool that's aligned with your business goals and structure. It should also set customers up for success.

Many email automation software options exist, such as AnyLeads, Leadfuze, MailChimp, Moosend, Versium Reach, and Hubspot Marketing Automation. Finding the right automation tool for your business can be tricky, but looking out for the following core features can help you separate the wheat from the chaff:

  • Personalization capabilities — You want your software to help you create personalized messages and experiences for your prospects, leads, or customers and nurture your relationship with them, so it needs to integrate seamlessly with your Customer Relationship Management (CRM) software.
  • A level of automation — The point of automated email prospecting is to enable you to automatically send messages and follow-ups based on customizable triggers or the touchpoints you've set. Any email automation tool that doesn't include this vital function is not worth your time.
  • Ease of use and customization — Automating your emails helps to save valuable time that can be better spent building personal connections with your customers. Opt for an easy-to-use tool with beautifully designed premade templates that you can easily customize to suit various use cases to maximize time savings.
  • Comprehensive analytics — A great automation tool tracks as much data as possible to determine what's working and whether you're meeting your goals and making a Return on Investment (ROI).
  • Mobile responsiveness — Since most people tend to check emails on their mobile phones, you need to pick an automation tool that prioritizes mobile optimization in its user experience. 
  • Dynamic list segmentation — Your personalization efforts can be hindered or helped by your email list segmentation, which should factor in each prospect or subscriber's essential and distinctive characteristics. If these characteristics aren't defined and separated, there will be nothing for the automation tool to personalize from. This is why choosing a tool capable of building and segmenting dynamic email lists is important.

Step 2. Come up with an aesthetically-pleasing design 

One of the quickest ways to annoy prospects and get them to stop reading your emails is by sending poorly designed emails. You want your emails to stand out, capture attention, and keep your prospects engaged from start to finish, so your design needs to be easy on the eyes.

Think about the user experience you want prospects to have when reading your emails, and organize your layout with that in mind. You don't want your messages to look disorganized, cluttered, or overwhelming so make ample use of white space.

Your email design should be responsive and evolve to enable optimal and easy viewing on any screen or device, whether a tablet, desktop, or mobile phone. Cross-device accessibility can help boost your email engagement and retention rates.

Step 3. Write your email's content

The content of your emails matters a lot because they will decide whether the prospect makes it to the end of each message. Rather than writing long paragraphs about your product's features or your company's value proposition, focus on the prospect and express how your product or service can improve their lives or solve their problems.

Brevity is key here. You'll have plenty of opportunities in the future to tell the prospect more about your brand and offerings if you play your cards right. So don't try to cram it all in there at once.

At each point in your funnel, your goal is to feed prospects short, sweet, and interesting content that pushes them to the next step without demanding too much of their time and attention. For example: 

cold email template

Source: Close

You can test out different tones in your emails to see which works best for your target personas. In the meantime, casual and friendly is always a good tone.

Keep in mind that you should tailor the Call-To-Action (CTA) and content of your messages to the phase of the customer journey that each prospect is in to ensure they stay relevant and targeted. For example, you can include a link to a landing page with videos, webinars, and other educational information about your products for prospects that don't know much about your business.

Prospects who are already familiar with your brand and offerings can be offered white papers, case studies, or a calendar link to schedule a conversation with a rep that will provide more details and answer any questions they might have.

Step 4. Test your email and tweak where needed

The only way to know if your prospecting efforts are paying off or if your strategy needs to be modified by keeping track of your campaigns. 

When you pay attention to your data, you will begin to uncover trends regarding engagement and customer behavior and develop insights that help you serve prospects better. When prospects feel seen, understood, and valued, they keep opening your messages and engaging with your CTAs until they finally convert. 

Some vital metrics that you cannot sidestep when measuring the effectiveness of your email prospecting campaigns include:

  • Open rate — This is the percentage at which people open each email you send. Low percentage points to problems with your sender information, subject line, first sentence, and email send times. Testing different variations of these and ensuring you're communicating with someone equipped with the power to make purchasing decisions can help boost your open rates.
  • Response rate — Your response rate is the percentage of people who replied to your emails. Little or no responses mean your messages aren't hitting the right notes. Positive responses indicate you're targeting the right people with the right message, while negative responses say the opposite.
  • Click-Through Rate (CTR) — What percentage of the emails you sent had at least one link clicked? That's your CTR. Whether you're trying to get prospects to visit a landing page, book a demo, download a case study or set up a meeting, you have to make sure they're clicking the links in your email. You can improve your CTR by repeating your links multiple times throughout the email and crafting more compelling messages, CTAs, and anchor text.

Four tips for maximizing success with email prospecting

Capturing, retaining, and converting your prospect's interest into sales for your business requires you to construct your emails thoughtfully. Here are some strategies that can help you accomplish this and increase the effectiveness of your cold email campaigns:

1. Choose your subject line carefully

Subject lines can be disastrous or highly impactful to your sales emails for something that only eats up a few words. If your subject line isn't interesting enough, it won't compel the prospect to open your email and see what you have to say.

Devote yourself to crafting a subject line that's simple, attention-grabbing, and doesn't sound to sales. Avoid making grammatical errors or using overly dramatic or clickbaity subject lines that could make your emails spam.

Nobody will be tempted to open an email with a subject line riddled with mistakes like extra spacing, brackets with form field labels, or even the wrong name because it shows that you don't care enough to pay attention to details. 

Write like you're addressing your email to someone you have a cordial relationship with without sounding overly familiar. Creating a sense of exclusivity or phrasing your subject line as a question can also help pique attention and dramatically increase open rates. For example, which of the emails below would you click on?

phrasing subject line

2. Personalize your emails 

Even though the prospect knows they are not the only one you're writing to, they will not appreciate seeing proof of that — so generic emails are an absolute no-no. You need to make your automated emails feel like they were written specifically for each prospect.

Start by using personalization tokens like their first name, company, title, and other distinguishing details. Then match each prospect to a customer persona based on demographics, interests, lead source, and pain points. Create a different set of automated messages for each persona that will be relevant to them.

CEO of CB Insights Anand Sanwal's analysis of 147 cold emails he received over two weeks revealed that 76% of the emails showed a lack of familiarity with his business. Naturally, he rejected them. His research shows that if you want to boost response rates, you need to research each prospect and find something interesting or unique about them or their business that you can weave into emails to personalize your messages further.

Visuals tend to be far more eye-catching, engaging, and easily recollected than words, so including them in your automated emails can aid in grabbing the prospect's attention.

Instead of writing a long explanation about a subject that may scare the recipient away, you can distill the key information into an infographic and let it explain and convey. Alternatively, you can drop a link to a video or landing page with educational resources that can shed more light on the topic or offer. 

You can also create animations online in a photo or video format and use them to demonstrate parts of your message. Or incorporate humorous images and GIFs in your emails to help relieve tension and make your emails feel more relaxed and comfortable. 

4. Add a professional signature. 

When crafting a sales pitch, the bulk of attention is usually given to nailing the perfect subject lines and opening. However, how you close your emails matters greatly, and if you mess it up, it can ruin all the amazing work you did initially. 

The end part of your email should always include a CTA that tells the prospect what you want them to do next after reading it. It's also a good place to include questions that can spark conversation by pushing the recipient to respond.

Finally, you must include a signature in your emails to avoid being unprofessional. Your signature should share important information about you, such as your name, company, and title.

You can even take things up a notch by adding a link to your website, a recent blog post, social media profiles, accolades you've received, or a free tool/resource from your company. 

Fast track your sales cycle 

Automating email prospecting can save you a lot of time, productivity, and resources that you can sew into parts of your business where human effort is needed for optimal performance. 

It's important to remember that email prospecting and automation are not one-and-done activities. You must keep experimenting and optimizing your strategies to improve outcomes and maximize sales.

Mark Quadros is a SaaS content marketer that helps brands create and distribute rad content. On a similar note, Mark loves content and contributes to several authoritative blogs like HubSpot, CoSchedule, Foundr, etc. Connect with him via LinkedIn or twitter.

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