Introduction
First and foremost, I want to emphasize that this is an excellent idea—one that has significant potential for success. The main reason it stands out is that larger companies struggle with executing hyper-local, personalized initiatives like this at scale. They lack the agility to form personal relationships with decision-makers in the way a smaller, more locally focused business can. This gives you an immediate and powerful advantage over big competitors.
However, the success of your outreach will largely depend on execution. Writing a great letter is just one component of a multi-touch outreach strategy. A well-crafted letter alone isn’t enough; it has to be supported by personalization, follow-ups, and direct engagement.
1. Keep It Concise and Impactful
One of the biggest mistakes people make when reaching out to high-level executives is being too wordy. Decision-makers don’t have time to read long letters. If your message isn’t clear and concise, it won’t be read at all.
Think about it from their perspective: Their inboxes and desks are filled with letters, proposals, and marketing materials every day. If your message is too long or feels generic, it will be discarded before they finish the first paragraph.
Instead, your letter should be direct and to the point:
- First sentence: Capture their attention.
- Second sentence: Clearly state the reason for writing.
- Third sentence: Provide immediate value or relevance.
- Closing sentence: Include a compelling call to action.
The goal is to spark their interest and get them to engage, not to overload them with information.
2. The Power of a Strong First Line
The opening line is arguably the most important part of the letter because it determines whether they continue reading. If it doesn’t immediately hook their interest, they will skim or discard it.
A weak opening would be something like:“I’m reaching out to introduce myself and my company.”
This is boring and generic—it sounds like every other sales pitch.
Instead, you need a strong and personalized hook:
- Mention a mutual connection or previous interaction:
- “I recently spoke with [Name] at your [Location] branch, and they suggested I reach out to you personally.”
- Ask a question related to their pain points or goals:
- “Have you ever considered how [solution] could help improve [specific metric] at your location?”
- Use a compelling fact or statistic:
- “Hotels that implement [your solution] have seen a [X]% increase in [key benefit] within six months.”
By making the first sentence engaging, relevant, and personalized, you increase the likelihood that they will continue reading.
3. Personalization Is Key
One of the biggest barriers in reaching executives is getting past their assistants or gatekeepers. Their job is to filter out anything that looks like a cold sales pitch or mass email.
If your letter is generic, templated, or impersonal, it will never reach the intended person. That’s why personalization is critical.
Here are a few strategies to make your letter stand out as personal and authentic:
- Always use their name. Never address it to a title like “General Manager” or “CEO of [Company].” Instead, do your research and find their actual name via LinkedIn, the company website, or by calling and asking.
- Reference something specific about their company. Mention their location, recent news about their business, or something you observed in your interactions.
- Include details from previous conversations. If you’ve spoken with someone from their team, mention their name and what they said.
For example:“I recently visited your [Hotel Name] and spoke with your manager, Stacy. She mentioned that you’re always looking for ways to improve guest satisfaction, which is why I wanted to personally reach out to you with an idea that could help.”
This level of personalization makes it impossible to ignore and distinguishes your letter from a generic template.
4. Multi-Channel Outreach: Don’t Rely on Just the Letter
While a well-written letter is a great starting point, you should never rely solely on written communication to reach decision-makers.
Instead, think of it as part of a multi-touch strategy where you:
- Identify the right contact – Find their email, phone number, and LinkedIn profile.
- Call first – Introduce yourself and let them know you’ll be sending a letter.
- Send the letter – Use it as a follow-up to reinforce your initial contact.
- Send a follow-up email – Reference the letter and ask if they had a chance to review it.
- Make a second call – If no response, follow up with another call.
This combination of direct contact, written communication, and follow-up increases the likelihood of success.
5. Avoid the “Salesy” Tone
Most executives and managers have a strong aversion to anything that sounds like a cold sales pitch. Their assistants are trained to filter out sales letters before they even reach them.
To avoid getting screened out, make the letter feel like a warm introduction, not a solicitation.
Instead of:“I’d love to set up a meeting to discuss how my company can help.”
Try:“I recently spoke with [Name] at your location, and they thought it would be valuable for us to connect. I’d love to get your thoughts on how we might be able to help with [specific challenge].”
This makes it feel more like a natural conversation rather than a hard sales pitch.
6. Make the Offer Clear and Compelling
Your letter should quickly communicate why they should care.
- Clearly state the benefit.
- Offer something of value with no pressure.
- Make it easy for them to respond.
For example:
Bad Example:“We offer high-quality internet solutions that can benefit your business. Let me know if you’re interested in learning more.”
Good Example:“I’d love to set up a time to stop by and offer a free trial at no cost or obligation. If you’re open to it, let’s schedule a time for me to show you how this works.”
A strong offer increases engagement and makes it harder for them to ignore.
7. Scaling the Outreach for Maximum Impact
Once you perfect the approach, the next step is scaling it efficiently.
- Create a flexible letter template that allows for quick customization.
- Build a list of targets using LinkedIn and online business directories.
- Dedicate time each week to outreach – set a goal for how many contacts you’ll reach out to.
- Track responses and follow-ups in a simple CRM or spreadsheet.
If it takes one day to craft the perfect message, it should only take an hour to customize it for the next recipient. Over a 40-hour workweek, you could easily reach 40+ prospects.
Let’s say one-third respond and half of those become clients—that’s a few new customers every single week.
By refining and scaling your outreach, you can turn this strategy into a repeatable process that drives consistent results.
Final Thoughts
This approach is a highly strategic way to get your foot in the door with decision-makers. The key takeaways are:
Make it personal – Find names, reference real conversations.
Keep it brief – Executives won’t read long pitches.
Use multiple channels – Combine calls, emails, and letters.
Avoid the salesy tone – Make it sound like an introduction, not a pitch.
Make the offer enticing – Provide value upfront with no pressure.
Scale efficiently – Systematize the process for maximum impact.
If executed properly, this strategy can be a game-changer for your business. Best of luck—I believe you’re onto something great! 