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How to Ensure Your Email Outreach Is Effective

SendtoWin has spent over 15 years mastering personalized email outreach and has $1.6B in pipeline to show for it. So the Apollo team asked them: how do salespeople create eyecatching cold emails that get responses? Here’s what founders Martin and Samuel have to say.

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Martin Aguinis

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Samuel Shandler

UPDATED Mar 31, 2025

5Min Read

That cold email — the one just spent the last 20 minutes writing — is one of 121 messages vying for your prospect’s attention today. 

Buyer’s inboxes are completely inundated with spam and promotional content and making your email stand out remains a significant challenge.

But at SendtoWin, we've spent over 15 years mastering the art of cold email to help companies improve B2B email deliverability and generate significant pipeline revenue. After years of testing our approach, we've discovered that the key to increasing email response rates is building around sales cold email strategy around personalization. 

We've seen these personalization strategies amplified with AI-driven sales tools, turning what was once an arduous, manual process into a scalable system that delivers truly targeted outreach. 

The results? Higher open rates, more meaningful conversations, and a significantly stronger pipeline. Here’s how to replicate it.

How personalization turns cold emails into conversions 

For sales reps, 9% of lost deals stem from a lack of relationship or trust. Another 15% are lost because of customer indecision (according to research from Apollo’s recent survey).

Trust and a sense of relationship create a connection that makes customers actually want to buy from your brand. They also help fuel decision making. 

And personalization helps establish that much needed trust and connection. 

Take Samantha McKenna, for example — founder of #samsales and quite literally the master of email personalization.

Her campaigns boast as high as a 43% open rate because of her intense focus on properly personalizating the subject line and cold email introduction. Email personalization, eventually, led her to expand company vertifcal by 1,333% in less than two years.

When you craft emails that reference specific pain points, recent company milestones, or industry challenges unique to your prospect, you’re saying something powerful: “I see you as an individual, not just another contact in my database.”

This level of attention creates instant differentiation in a crowded inbox and dramatically increases your chances of starting a genuine conversation.

Much of our personalization philosophy is aligned with what Sam talks about in her Master Class on the Apollo Academy. Give it a watch here.

The 5 steps of persona-based personalization

To write interesting emails for your prospects, you have to understand them.

And to do that at scale, it can be helpful to bucket them in terms of your ideal customer profiles, or “personas.”

This way, you can better personalize your email communication to address their specific interests, challenges, and goals. This makes your outreach more relevant, which could lead to increased email response rates and more engaged prospects. You can also speak to the pain your prospects might feel — setting the scene for what we call a Pain Value Credibility (PVC) email framework. 

A persona-based PVC framework breaks through the noise, captures the recipient's interest, and encourages them to take the desired action. Here’s a step-by-step look at building your own.

Step 1: Segment your target market

Start by identifying the key segments of your target audience. Gather data through market research, customer interviews, and analysis of your current customer base to build detailed personas. Each persona should include information such as:

  • Job title and role
  • Industry and company size
  • Demographic details
  • Key challenges and pain points
  • Goals and aspirations

Defining these attributes above sets you up to quickly hone in on qualified sales leads within Apollo without applying a lot of manual filters. 

Step 2: Identify your prospects’ biggest pains

Mentioning specific pain points automatically make it a personalized interaction rather than a generic sales pitch. 

But uncovering pain points specific to each prospect takes tons of time. 

With the right prompts though, AI tools like Apollo's AI Power-ups can do the heavy lifting during pain point research. By asking AI to analyze recent company news, earnings reports, press releases, and more, you can reduce hours of manual research. In some cases, using AI can even 10x productivity during the research phase. 

Try it: Use this AI prompt template in Apollo to identify company pain points and challenges your product can solve.

Step 3: Highlight the value your service provides

A clearly communicated value proposition — that probes those pain points — motivates prospects to act. 

By focusing on the value your service offers to them, you shift the conversation from selling to helping. This can change the dynamic of your interaction, making the prospect see you as a partner rather than just another vendor — enhancing trust and creating the foundation for a budding relationship.

Clearly articulating the benefits of your service also helps differentiate your offering from competitors. It's important to communicate how your solution is unique and why it's the best fit for their specific needs.

Step 4: Establish the credibility of your company

In a famous experiment, 65% of participants agreed to get administered shocks simply because the person who was giving them instructions was wearing a lab coat.

This isn’t exactly applicable to cold emailing but the idea is this: people trust those they perceive as experts or authorities.

Which is why establishing credibility is such a critical factor in any business relationship, especially in cold outreach where there's no prior relationship. 

Put on your “lab coat” by highlighting testimonials, case studies, or notable achievements of your services. Demonstrating your company's expertise and authority in the field reassures prospects that they're dealing with knowledgeable professionals who understand their industry and challenges.

Step 5: Get your timing right 

Timing can significantly impact the effectiveness of your cold email outreach. Paraform co-founder John Kim agrees that timing is everything. 

When I reply to cold emails, it's not because the copy is stellar. It's when the timing is right, when I need that product right then.

- John Kim, Founder at Paraform

Not only should you consider when a prospect needs a product, you should also consider when’s the best time to send the email — whether it’s simply touching on a specific pain point or providing right-on-time product information.  

Research suggests that emails sent on Tuesday, Wednesday, or Thursday, particularly around mid-morning (10 AM to 11 AM), tend to have higher open rates. However, the best time can vary based on your target audience's habits and preferences, so consider A/B testing different send times to find what works best for your prospects.

Building a personalized cold email piece-by-piece

While we use several software providers and partners, Apollo stands out as one of our favorites. Specifically leveraging Apollo's cutting-edge AI tools. More specifically, Apollo's AI sequence builder and cold email AI generators help us craft personalized narratives that not only reach inboxes but resonate well with prospects.

AI can reduce manual work and enhance customer engagement — which is likely why 61% of sales professionals have found AI has positively impacted their ability to close deals. And why 57% of sales teams plan to further integrate AI and automation into their sales process in the future. (Again, from Apollo’s recent state of sales survey 👀)

Here are some of the ways we’re already using Apollo, across each element of our email copy, to improve B2B email deliverability and make our cold emails get noticed.

Subject Line: Use Apollo's A/B testing feature to determine which subject lines resonate most with your audience. Keep it relevant and personalized, possibly hinting at a solution to a known challenge or an opportunity for improvement.

Example: "Boosting {{CompanyName}}'s Q3 Sales Performance: A Strategic Approach"

Opener/Hook: Mention a recent achievement, news about the prospect's company, or a mutual connection to grab their attention. Apollo's AI email generator can automatically write a personalized opening line that will give you a headstart.

Example: "Congratulations on {{ProspectCompany}}'s recent product launch—impressive work in such a competitive space!"

Pain Point: Address a specific challenge you know the prospect is facing, using insights from industry trends or similar companies.

Example: "Like many in {{Industry}}, you might be experiencing longer sales cycles and increased customer acquisition costs."

Value Proposition: Clearly articulate how your solution can address the pain point. Use Apollo to segment your audience and tailor your value proposition to each segment's unique needs.

Example: "Our targeted email campaigns are designed to shorten sales cycles and reduce acquisition costs by engaging high-intent leads."

Credibility: Share success stories or case studies relevant to the prospect's industry or role. Highlight your team's expertise and notable achievements. 

Example: "Our approach has helped companies like {{SimilarCompany1}} and {{SimilarCompany2}} achieve a 30% reduction in sales cycle length."

Call to Action (CTA): End with a clear, compelling CTA that encourages the prospect to take the next step. Make it easy for them to engage further, whether it's scheduling a call, signing up for a demo, or downloading a case study.

Example: "Would you be open to a brief call to discuss how we can achieve similar results for {{ProspectCompany}}?"

Putting it all together

Here's how a complete email might look:

Hi {{first_name}},

Congratulations on {{company_names}}'s recent product launch—impressive work in such a competitive space!

Like many in {{industry}}, you might be experiencing longer sales cycles and increased customer acquisition costs. Our targeted email campaigns are designed to shorten sales cycles and reduce acquisition costs by engaging high-intent leads.

Our approach has helped companies like [insert similar company] and [insert another similar company] achieve a 30% reduction in sales cycle length. Would you be open to a brief call to discuss how we can achieve similar results for {{company_name}}?

Best,  

{{sender_first_name}}

By focusing on personalization, addressing real pain points, and clearly communicating your value, your cold emails will leave prospects curious to learn more about how you can solve their challenges. Start using these email outreach best practices and show your future customers you understand them. 

After all, landing your next big deal could all start with one well-crafted email. 

If you are a B2B company interested in boosting your pipeline, you can reach out to us at SendtoWin.com.

About SendtoWin

SendtoWin is a B2B lead generation service that has driven over $1.6 billion in pipeline and $100 million in revenue for their clients, using the strategies that built success at top-tier companies and supercharged them with AI and industry best practices to help businesses globally. Their expert team is made up of executives from Google, Databricks, and Oracle as well as Stanford MBAs and Forbes honorees that specialize in crafting high-performing cold email and LinkedIn campaigns. From Fortune 500 enterprises to fast-growing startups backed by leading investors like Sequoia, Menlo Ventures, Fidelity, Fine Structure Ventures, Raptor Group, and Y Combinator—we empower businesses to grow faster and smarter.


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