The Ultimate Guide to Automating Email Prospecting Without Sounding Like a Robot

Email remains one of the most powerful channels for sales prospecting, yet many salespeople struggle to get results. Consider these eye-opening statistics:

• The average salesperson only makes 2 attempts to reach a prospect, but it takes an average of 8 touches to get a meeting booked (Brevet)
• 80% of prospects say "no" four times before they ultimately say "yes", but 92% of salespeople give up after hearing "no" four times (Marketing Donut)
• Only 23.9% of sales emails are opened (HubSpot)

Clearly, there‘s massive room for improvement in how most salespeople approach email outreach. The key is finding the right balance between personalization and productivity. You need to send tailored messages that resonate with each individual prospect, but you can‘t spend hours writing one-off emails that may never even get opened.

The solution? A strategic process for automating email prospecting – one that allows you to customize at scale while still sounding like a human, not a script-reading robot. Here‘s how to do it step-by-step:

Step 1: Lay the Groundwork

Effective email campaigns don‘t just materialize out of thin air – they require some upfront planning and preparation:
– Develop a set of buyer personas so you understand your target prospects‘ goals, challenges, and preferences
– Create a content library mapped to different personas and buying stages (e.g. blog posts, ebooks, case studies, product sheets, etc.)
– Write a master set of email templates and call scripts that can be mixed, matched, and modified
– Implement a CRM and sales engagement platform to track prospects and automate sequences

Step 2: Craft Click-Worthy Subject Lines

No matter how brilliant your email copy, it‘s all for naught if your message goes unopened. To maximize your chances of piquing a prospect‘s interest, try these subject line approaches:
– Personalize with the prospect‘s name or company
– Create a sense of exclusivity or timeliness (e.g. "Bob, your private invite inside")
– Ask an intriguing question (e.g. "Quick question about [prospect‘s goal]")
– Mention a mutual connection or interest
– Keep it concise – aim for 6-10 words

Here are a few examples:

• "[First Name], quick question for you"
• "We can help [Company] achieve [Goal]"
• "Idea for [Company]‘s [Project/Initiative]"
• "Exclusive invite for [First Name]"

Step 3: Personalize Your Message

With your foot now in the door thanks to a strong subject line, you have to quickly demonstrate your message is worth reading. Do this by customizing your email to show you‘ve done your homework:
– Use merge fields to dynamically insert prospect info like first name, company, title, industry, etc.
– Reference a piece of company news, recent social media post, or relevant trigger event
– Mention a mutual connection, if you have one
– Highlight a specific challenge they‘re likely facing based on your persona research

Check out this example:

Even though this message follows a template, these small personalized touches make it feel one-to-one. Aim to include at least 2-3 customized tidbits in each email.

Step 4: Keep It Concise and Conversational

Resist the urge to info-dump everything about your company and product in the first outreach. Instead:
– Get to the point quickly and focus on the prospect, not yourself
– Use short sentences and paragraphs
– Write like you speak – keep the tone casual and friendly
– Bold key phrases and use bullet points to aid scanning
– Cut any fluff – if a sentence isn‘t essential, delete it

Here‘s an example putting those tips into practice:

Step 5: Experiment with Eye-Catching Visuals

Adding a relevant image, gif, or video screenshot can spice up your message and make it more memorable. For example:
– A humorous gif to break the ice
– An educational infographic related to the prospect‘s industry
– A chart showing results you‘ve achieved for similar companies
– A headshot of yourself or your company‘s founder for a human touch

Just make sure the visual adds to your message rather than distracting from it.

Step 6: Drive Action with Content and CTAs

The goal of your email is to motivate the prospect to take the next step, whether that‘s booking a meeting, downloading content, or simply responding. To make it happen:
– Include 1-2 links to relevant content (blog post, case study, product page, etc.)
– Have one clear call-to-action button (Schedule a Call, Download Now, etc.)
– A/B test different CTAs to see which get the most clicks

Step 7: Scale with Automated Sequences

With your customizable templates locked and loaded, it‘s time to put your prospecting on autopilot. Using sequences in your sales engagement software:
– Create multi-touch campaigns for each buyer persona with 5-12 emails per sequence
– Schedule emails to deploy at set time intervals (e.g. Day 1, Day 3, Day 7, etc.)
– Mix up the content and CTAs in each email to add value before going for the ask
– Include if/then logic to stop sequences if a prospect opens, clicks, or replies
– Set tasks for yourself or team members to call or follow-up personally

Here‘s an example sequence for a demand generation persona:

By automating your email prospecting, you can drastically increase your activity levels while still tailoring your messaging. Monitor your open, click, and response rates to identify top-performing templates and optimize your sequences over time.

The Best Sales Email Automation Software

To execute this process efficiently, you need the right tools. Here are some of the best solutions for automating, personalizing, and tracking sales emails at scale:

1. HubSpot Sales Hub

• Email sequences with reporting and A/B testing
• Predictive lead scoring
• Meeting scheduling
• Inbound calling
• Conversation intelligence
• Automated data entry and task logging

Pricing: Starts at $45/month

2. SalesLoft

• Email, phone, and social outreach campaigns
• Live chat and inbound communications
• Automated Salesforce logging
• Engagement analytics
• Mobile app for on-the-go outreach

Pricing: Starts at $125/user/month

3. Outreach

• Multichannel sequences (email, phone, text, social)
• AI-powered conversation intelligence
• Advanced reporting and forecasting
• Seamless CRM integration
• GDPR-compliant

Pricing: Starts at $100/user/month

4. Reply

• Email sequences with if/then workflows
• Call recording and voice mail drops
• LinkedIn automation
• Zapier integrations
• Chrome extension

Pricing: Starts at $70/user/month

5. Mixmax

• Two-way email sync with Salesforce
• One-click meeting scheduling
• Attachment tracking
• Automated drip campaigns
• Team templates and reporting

Pricing: Starts at $24/user/month

6. Yesware

• Real-time email tracking
• Custom template library
• Link click detection
• Salesforce and LinkedIn integration
• Presentation tracking

Pricing: Starts at $15/user/month

Go Forth and Automate (Thoughtfully)

At the end of the day, email prospecting is both an art and a science. While automation is incredibly powerful, it‘s not a magic wand. Simply blasting prospects with generic messages is a quick way to end up in the spam folder.

The key is combining automated sequences with personalized touches to create the ideal prospect experience at scale. Invest the time upfront to research your buyers, craft compelling messaging, and set up your sequences. Then use technology to put your outreach efforts on cruise control.

By striking the right balance, you can fill your pipeline with more qualified leads in far less time. So what are you waiting for? Go automate your prospecting and close more deals!