How to Automate LinkedIn Messaging in 2025? Hands-on Guide

Here at Reply, we’re big believers in sales outreach as an effective way to build a reliable pipeline and grow your business. Yet, its success depends mostly on the three key factors: targeting, channels in use, and your ability to scale it.

If targeting is pretty obvious – the days of the “spray and pray” approach to cold outreach are long gone! – the choice of outreach channels and strategies to ramp up the whole process might still be the topic of discussion. 

Whether you firmly believe in email-only outreach or choose to smile and dial, both channels can be automated to increase your reach. But what if you want to get ahead of the competition and adopt LinkedIn as your sales engagement channel? Automation doesn’t seem so easy in this case. Yet, it’s still possible.

In this article, we’ll talk about how to automate LinkedIn messages and help you choose the best tool for the job.

Why automate LinkedIn? (including LinkedIn message automation)

So, why should you even consider using LinkedIn automation? Surely, it’s all about working smarter, not harder, to make the most of this powerful networking platform.

1. Efficiency and time-saving

First off, let’s talk about efficiency.

LinkedIn can be a bit of a time-sink, right? Manually sending connection requests, writing messages, and posting content can eat up hours of your day.

With automation tools like Reply, you can schedule posts, send connection requests, and even set up follow-up messages. This frees up your time to focus on what really matters – like having meaningful conversations and building genuine relationships.

Source: Exploding topics

2. Enhancing your reach and engagement

Automation can significantly boost your reach and engagement. Imagine having a tool that helps you connect with hundreds of people in your industry every week, or one that ensures your content gets posted at the optimal times for maximum visibility.

These tools can help you stay active on LinkedIn without having to be glued to your screen all day.

The result? More visibility, more engagement, and ultimately, more opportunities.

3. Consistent content posting

Consistency is key on LinkedIn. Regular posting keeps you on your network’s radar and positions you as an active member of the community.

But let’s face it, consistently coming up with and posting content can be tough. Automation tools let you plan and schedule your posts in advance. You can set it and forget it, knowing your content will go live at the perfect times, keeping your profile active and engaging without daily effort.

4. Better analytics and insights

Many LinkedIn automation tools come with built-in analytics.

This means you can track what’s working and what’s not, giving you valuable insights into your audience’s behavior. Are your posts getting more engagement in the morning or evening? Which types of posts get the most likes and shares?

With this data, you can tweak your strategy for even better results.

5. Scalability

As your network grows, managing it manually becomes almost impossible.

Automation allows you to scale your LinkedIn activities effortlessly. You can handle a larger number of connections, messages, and posts without feeling overwhelmed. This scalability is crucial for anyone looking to grow their professional network rapidly and efficiently.

And before we dive into ‘how to automate LinkedIn messages,’ let’s discover why LinkedIn is so important in the sales engagement process.

Where is LinkedIn in sales engagement process?

Although emails and phone calls are considered the traditional business communication channels, sales prospecting can be performed using many other tools. Depending on the specifics of your audience, this can be anything from text messages to snail mail.

However, the social media here play by far the most vital part. And since outreach is usually applied in B2B sales, LinkedIn has already become the go-to platform for most SDRs.

Why is that, you ask? Let’s see…

• Vast pool of contacts. There are 1.03 billion on the platform, mostly business professionals 

Source: LinkedIn

• Active engagement. The platform saw a 55% increase in conversations among connections in 2021 with an average session length of 6:07 minutes, according to the reports. 
• Business-related audience. The data shows that nearly 62% of LinkedIn users worldwide are between the ages of 25 and 34 years old. Moreover, the platform claims to reach more than 1+ billion business decision-makers. 
• Convenient toolset. LinkedIn comes with additional features to help you find and engage your prospects, most free to use. Even its basic search gives you enough tools to sort out the perfect-fit prospects.

Source: LinkedIn

• Source of information. Prospects themselves turn to the platform for research and thought leadership on a variety of topics, which makes engagement on LinkedIn low-hanging fruit.

On the other hand, LinkedIn outreach definitely takes some time and grit to ace. Among the most important downsides of the platform are its strict usage policies and limitations. As a result, it’s difficult to automate LinkedIn messages (unlike email, for example).

Does LinkedIn send automated messages?

Well, it depends on what type of LinkedIn automated messaging we’re talking about.

In case you want to set up an autoresponder or make the messaging a bit more prompt, LinkedIn offers a set of solutions to facilitate that. This includes smart response suggestions for quick reply.

If you want to automate LinkedIn messaging at scale, i.e., send a large number of personalized messages to your contacts or connect with people outside of your network, consider using third-party tools to orchestrate the process.

We will get to the software recommendations and overall process explanation later. But first, let’s address the most burning question about LinkedIn message automation – it’s safety.

Is it safe to send automated LinkedIn messages?

There’s a lot of speculation when it comes to LinkedIn automation. Some say that it’s a sure way to get your account blocked. Others have been successfully using various tools for years without any consequences. 

Technically speaking, any form of automation falls into the don’ts of the platform’s User Agreement. This includes using “bots or other automated methods to access the Services, add or download contacts, send or redirect messages.”

Some sources even claim that there’s a list of such tools that have been officially banned by LinkedIn!

However, considering the abundance of LinkedIn automation tools out there, we can state that the policy isn’t so strict or it’s easy to bypass it. If you do your research on the subject, you can find a ton of information on how it works to make such tools safe to use. 

Without getting into too many technical details, it all depends on the platform limits. This may include the number of API calls that the tools make when running tasks on LinkedIn to automate certain tasks as well as more common limits, e.g., messages and connection requests sent. 

So, answering the initial question: Yes, sending automated LinkedIn messages can be safe if you use trusted tools and stay within the platform line to avoid setting off any alarms.

What do you need before automating LinkedIn messages?

Before you dive into “can you send automated messages on LinkedIn” and how to do it, there are a few things you need to have locked down. Think of it like preparing for a marathon; you wouldn’t just throw on some sneakers and start running. 

Let’s make sure you’re set up for success.

First, fix your LinkedIn profile

Your profile is your first impression, so it better look good. A half-hearted profile screams, “Don’t take me seriously.” 

Start with a killer headline that shows what you bring to the table. Polish your summary to highlight your expertise and achievements in a conversational tone. If you’re in sales, for instance, don’t just say “Sales Professional”—say something like, “Helping SaaS companies grow revenue through tailored sales strategies.”

Oh, and your photo? Make it professional but approachable. No blurry selfies, okay? Use tools like Canva to add a sleek banner to your profile for extra flair.

Have a game plan

Before you automate anything, get crystal clear on what you want to achieve. Are you connecting with potential clients, scouting for new hires, or just growing your network? 

Whatever the goal, know your audience.

Spend some time researching the people you want to connect with. LinkedIn’s search filters are your best friend here. Narrow down by job title, location, industry—whatever makes sense. And when it comes to your message, keep it short and to the point. Nobody has time for an essay in their inbox.

For example:

“Hi [Name], I noticed we share an interest in [Topic]. Would love to connect and exchange ideas!”

See? Simple, friendly, and relevant.

Pick the right automation tool

Not all tools are created equal, and some can get you booted off LinkedIn faster than you can say “Terms of Service.” Look for tools like Reply.io—these are designed to play nice with LinkedIn’s rules. The key features you need? Daily limits to keep your activity looking natural, analytics to track your performance, and personalization options to avoid sounding like a robot. The Reply LinkedIn automation feature has it all.

Start small. Test your messages with a handful of people before scaling up. If the response rate is low, tweak your approach.

Warm up your presence

If you’ve been a LinkedIn ghost, popping out of nowhere with automated messages isn’t going to land well. Spend a week or two warming up your account by engaging with your network. Comment on posts in your niche, share some insights of your own, or even just hit the like button.

This way, when you reach out, people are more likely to recognize your name and respond.

Personalize, even when automating

Automation doesn’t mean you spam the same message to everyone. The trick is to make your outreach feel personal, even at scale. 

Mention their recent activity or a shared interest. Tools can help you pull in details like names, job titles, or company names, but it’s on you to add that extra human touch.

If someone’s posted about a recent achievement, congratulate them. If their company just made the news, reference it. These small tweaks show you’re paying attention.

Be ready for things to go wrong

Automation isn’t foolproof. Maybe your tool glitches, or LinkedIn tightens its restrictions. 

Stay flexible. Monitor your inbox and jump in manually when needed. If you’re pushing too hard—sending too many requests or messages in a day—LinkedIn might flag your account. Keep it steady and natural.

Stay open to tweaks

The first version of your outreach probably won’t be perfect, and that’s okay. Treat it as a work in progress. Test different messages, experiment with tone, and track what gets the best results. 

Maybe a casual tone works better than a formal one, or a question sparks more responses than a statement. Keep refining until you find your sweet spot.

Get these essentials in place, and you’ll be ready to automate like a pro. LinkedIn automated messages are powerful, but only when you’re strategic about them. Nail the prep work, and you’ll be connecting with the right people in no time.

How do I create an automated message in LinkedIn?

Now, let’s get down to business and see how this works in practice. First of all, it’s worth noting that there are a few types of messages you can send via LinkedIn: 

• InMails that you can send to anyone (as a paid option) and
• direct messages that can be sent to your 1st degree connections (absolutely free of charge).

You can also include short, personalized notes into your connection requests using automation tools. Depending on the type of message you want LinkedIn to automate, the templates and certain details of the process might vary.

As mentioned earlier, you can only send automated messages on LinkedIn using dedicated third-party tools. So, the first step of the process would be to connect your LinkedIn account to that tool.

You can find detailed instructions on how to do that with Reply. 

After that, the process is pretty much the same, regardless of the software you use:

• Get a list of contacts you want to message. You can either research the matching prospects manually or import a ready-made list from a trusted data provider. Just make sure the list contains valid LinkedIn profiles. 
• Craft your template based on the type of message you will be sending. The most important element of any outreach message is personalization. Since you will be sending automated messages, you might want to use customization variables/snippets or advanced personalization options with images or video.
• Set up the sequence with automated LinkedIn messages. This involves the schedule – the number of messages you want to send to each prospect within the campaign and their frequency.

Once you’re set, you can launch the sequence and it will run on autopilot. If the prospect responds, most tools will stop sending automated messages immediately.

Pro tip: Amplify your LinkedIn messages with multichannel engagement

If you’re looking to get the most out of your outreach campaign, depending on just one channel isn’t the best strategy. Consider mixing a few channels and using various types of interactions instead. Consider using Reply for it.

For example, viewing a prospect’s profile or sending a connection request on LinkedIn prior to dialing them directly or reaching out via email can be a great way to break the ice. You can either refer to this in your introduction or use it as a read for outreach. This can also help you get your face and name in front of the prospect’s eyes so you don’t sound like a complete stranger.

The same logic can also be applied the other way around. A subtle LinkedIn touch can be a great follow-up strategy in case your previous email or call has been ignored.

What are the dos and don’ts of writing LinkedIn messages?

No matter if you’re manually typing or letting automation do the heavy lifting, there’s a fine line between being engaging and being annoying. You don’t want to be that person—the one whose messages get ignored or worse, reported.

Here’s a quick guide to help you nail it. And yes, we’ll keep it super-practical with a handy table to break it all down:

Do’s	Don’ts
Keep it short and to the point. Nobody has time for an essay. Aim for 3-5 sentences max.	Don’t write a wall of text. Long messages scream “I’m trying too hard” and will likely get ignored.
Personalize your message. Mention their name, job title, or something specific from their profile (e.g., a recent post).	Don’t copy-paste generic templates. “Hi, I see we have mutual connections. Let’s connect” isn’t cutting it anymore.
Focus on the recipient. Show interest in their goals, work, or achievements. Make it about them, not you.	Don’t launch straight into a sales pitch. No one wants to buy from a stranger five seconds after connecting.
Start with a friendly, warm tone. Treat it like a casual conversation, not a formal business email.	Don’t be overly formal or stiff. Phrases like “To whom it may concern” belong in the last century.
Include a clear call to action. End with a simple ask, like “Would you be open to a quick chat next week?”	Don’t make them guess. If your message lacks a purpose, they’ll ignore it.
Proofread before hitting send. Typos can kill your credibility, especially on LinkedIn.	Don’t spam multiple follow-ups. If they’re not interested, move on. No need to be pushy.
Offer value upfront. Share a resource, a tip, or a compliment—it’s a great icebreaker.	Don’t just ask for favors. Networking is a two-way street. Give before you ask.

Let’s also break down some examples

• Do this (because it’s personalized, short, and has a clear purpose):

“Hi [Name], I saw your recent post about [Topic], and it really resonated with me. I’d love to connect and exchange ideas on [Shared Interest]. Let me know if that sounds good!”

• Don’t do this (because it’s all about you, not them, and sounds salesy right off the bat):

“Hi, I noticed you work in [Industry]. I offer [Product/Service] that could really help your business. Let’s connect so I can tell you more!”

Also, remember: Not every message will land, and that’s okay. 

Experiment with your tone, the type of personalization you use, and even the timing of your outreach. For example, mornings or midweek tend to get higher response rates. Track what works, and refine your approach.

What are examples of high-performing LinkedIn outreach templates?

Now for the fun part—templates! The best outreach messages don’t feel like templates at all. They’re short, personal, and designed to start a genuine conversation. 

No matter if you’re connecting for business, networking, or something in between, here are 10 high-performing LinkedIn outreach templates you can adapt to fit your style.

The classic networking opener

Perfect for building your professional network without coming off as pushy.

The “I loved your post” hook

Use this when someone has posted something interesting recently.

The problem-solver pitch

Great for sales or B2B outreach, but keep it subtle.

The flattery + value combo

People love compliments, but keep them genuine.

The mutual connection mention

If you share a connection, leverage it to make your intro feel warmer.

The straight-to-the-point ask

Sometimes, simplicity wins.

The event follow-up

Use this after meeting someone at a webinar, conference, or networking event.

The resource sharer

Start by offering something valuable, like a tip, article, or resource.

The aspiring learner

Position yourself as someone eager to learn from their expertise.

The warm reconnect

Use this for people you’ve interacted with before but haven’t spoken to in a while.

Process automation solutions for LinkedIn

One of the emerging sales tech trends, LinkedIn automation has already become a battleground where dozens of tools compete with each other while trying to navigate the limitations set by the platform itself. And I’m definitely curious to see who will win!

At Reply, we’re always up for a challenge too. That is why we’ve built the automated LinkedIn touchpoints, including message sending, into our core sales engagement platform. Based on extensive research and in-depth technical understanding of the platform as well as the key aspects of cold outreach automation in general, this feature is fully operational and safe to use. And you’re welcome to try it out.

If you want to do your own research first, we have some useful tips you can use as a guidance. But first, let’s talk about all the LinkedIn activities you can automate using such tools (for now excluding how to automate LinkedIn messaging).

Can you automate other LinkedIn activities?

We’ve already talked about the automated LinkedIn messaging sending in detail, but there are more activities to streamline here. For example, automated LinkedIn prospecting might also include other types of touchpoints, like profile views, connection requests, content interactions, etc. 

Just as in the case of automated LinkedIn messages, the software of your choice will perfectly imitate your behavior performing those actions on your behalf. All you need to do is provide the access to your personal profile.

Speaking of the more general use case, not just direct outreach, there are also tools to automate content publication or even further interactions in the comments (via the so-called “engagement pods”). 

While having some help getting your posts out is generally ok, robotic interactions with the said content are known to be one of the worst practices for LinkedIn automation. The unnaturally high number of likes and generic comments may raise some red flags and get your account banned.

How to choose the best LinkedIn automation software?

With a few established leaders in the industry, new tools emerge every year (if not quarter), offering a more convenient, safer, or more integrated way to automate messages in LinkedIn and orchestrate other activities.

That said, there are a few criteria to pay attention to when shopping around for a suitable solution:

• Safety and limits. Of course, you should be aware of the existing platform limits and always keep them in mind. However, the tool you choose should provide additional safety nets so you don’t get carried away and violate the platform policies. 
• Types of touchpoints. With direct messages being a kind of must-have for automation, the ability to streamline profile views or connection requests is also a way to diversify your outreach and make it more effective.
• Personalization. There are many ways to make your messages feel warm at scale. This includes variables – merge fields in the message automatically populated with the relevant data – as well as visual elements like images, videos, or GIFs (typically via third-party integrations).
• Multichannel engagement. As mentioned above, LinkedIn outreach is great, but if used in combination with email, calls, and other channels, it could be a real game-changer.
• Integrations. Any software you add to your stack should work well with the rest of the tools, be it CRM, data sourcing and enrichment, etc.

Based on these parameters, Reply seems like the best LinkedIn automation software. 

We care about your safety, offer various types of touchpoints (all automated for your convenience), dynamic personalization variables you can use in your messages, extra channels to boost your performance, and a ton of integrations to make it an integral part of your sales stack. And the best part is that you can try it before you buy it with our free trial.

If you’re looking for more suggestions, there’s an exhaustive list of vetted tools in our Sales Tools Catalog.

How can you use LinkedIn automation effectively?

Alright, let’s get real about LinkedIn automation. When done right, it’s like having a superpower that saves you hours of manual work and helps you connect with the right people at scale. But if you go about it the wrong way, it can backfire—hard. Think spam complaints, account restrictions, and awkward conversations.

So, how do you use LinkedIn automation the right way? Let’s break it down step by step, keeping it practical and foolproof.

1. Start small and test the waters

Before you go all-in, run small-scale tests. Think of automation as experimenting with recipes—you want to see what works before serving it to the crowd.

Here is how to do it right:

Use your automation tool to send out a small batch of connection requests or messages (20-30 at first). Monitor the response rate. If people aren’t replying, tweak your message templates or targeting filters.

2. Stay within LinkedIn’s limits

LinkedIn has daily limits on connection requests and messages. Exceed them, and you risk getting flagged. The trick is to make your automated activity look as natural as possible.

Get it right this way:

Limit connection requests to 50-80 per day if your account is new or inactive.

Keep message volume low initially—around 20-40 messages per day.

Gradually increase your activity over time to “warm up” your account. Most automation tools, like Expandi or Zopto, let you set daily limits. Use these features.

3. Target the right people

Automation is only as good as the list you feed it. If you’re targeting the wrong audience, no amount of automation will help.

Your best bet:

Use LinkedIn’s advanced search filters to narrow down your audience. For example, filter by job title, industry, location, or even specific keywords. Once you’ve nailed your audience, feed that list into your automation tool.

4. Craft messages that feel personal

Even with automation, your messages should feel human. Nobody likes generic, robotic outreach.

How to do it right:

Use placeholders like {{FirstName}} or {{CompanyName}} to make your message feel personalized. But don’t stop there—add a personal touch. Reference their recent activity or something specific about their profile.

Example:

“Hi {{FirstName}}, I saw your post about [topic]—really insightful! I’d love to connect and learn more about how you’re tackling [specific challenge].”

5. Engage before you automate

Automation works best when people recognize your name. If you’ve never engaged with someone before, your message might feel like it came out of nowhere.

How to make it work:

Spend a week or two liking, commenting on, or sharing posts from the people you plan to reach out to. Even a quick, thoughtful comment on their latest post can put you on their radar.

6. Track metrics and refine your approach

Automation isn’t a “set it and forget it” deal. You need to monitor how things are performing and adjust accordingly.

How to do it right:

Most tools offer analytics—use them! Track metrics like response rate, connection acceptance rate, and follow-up engagement. If something’s not working (e.g., people are ignoring your messages), experiment with different templates or adjust your targeting.

7. Don’t skip follow-ups

A lot of people won’t respond to your first message, and that’s fine. But a gentle follow-up can often nudge them into replying.

Here’s how you nail it:

Schedule an automated follow-up a week after your first message. Keep it light and friendly, like:

“Hi {{FirstName}}, just wanted to follow up on my last message. No pressure—let me know if this is something you’d be open to discussing!”

8. Blend automation with human interaction

Automation is a tool, not a replacement for real conversations. Use it to start connections, but be ready to step in manually when someone replies.

How to do it right:

Check your inbox daily and respond to messages personally. Automated responses can feel cold, so take the time to write thoughtful replies.

9. Stay compliant with LinkedIn rules

Automation is awesome, but LinkedIn doesn’t love it. To stay safe, don’t go overboard.

How to make it work:

Avoid sending spammy or irrelevant messages.

Use tools that stick to LinkedIn’s guidelines, like Expandi or MeetAlfred, rather than risky browser plugins.

Stay under the radar by mixing in manual activity, like posting content and engaging with your network.

What metrics should you track for LinkedIn messaging campaigns?

Alright, you’re running your LinkedIn messaging campaign, but how do you know if it’s actually working? That’s where tracking the right metrics comes in. Don’t worry—it’s not rocket science. I’ll walk you through the key numbers to keep an eye on, how to calculate them, and what they tell you. 

Plus, there’s a handy table at the end to tie it all together.

Metric	What it tracks	Formula	Good benchmark
Connection request acceptance rate	% of accepted connection requests	(Sent requests / Accepted requests​)×100	30%-50%+
Response rate	% of people who reply	(Messages sent / Replies​)×100	20%-40%+
Follow-up success rate	% of replies from follow-ups	(Follow-ups sent / Follow-up replies​)×100	20%-30%+
Click-through rate (CTR)	% of link clicks	(Messages with links sent / Clicks​)×100	10%-20%+
Conversion rate	% of desired actions taken	(Total sent / Conversions​)×100	5%-15%+
Bounce rate	% of failed requests/messages	(Total sent / Bounces​)×100	Under 5%-10%
Engagement rate	Overall interaction %	(Messages sent / Total interactions​)×100	25%-35%+

When you’re tracking the right numbers, LinkedIn messaging goes from guesswork to a data-driven strategy. Keep it simple, check your metrics regularly, and tweak your approach based on what’s working.

That’s how you turn campaigns into results!

Final word

The world’s most popular business networking platform, LinkedIn is a powerhouse that drives traffic, engages prospects, builds your reputation, and sells. It offers a ton of opportunities for SDRs and salespeople. 

The key here is to know how to use them to your best advantage. That is why you should consider LinkedIn automation messaging and know how to automate messages on LinkedIn clearly to avoid roadblocks.

Automating your LinkedIn touchpoints, including messages, can make a big difference when it comes to sales development and prospecting. Essentially, it allows you to spend less time contacting prospects manually, and more time building rapport, nurturing relationships, and closing deals.