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Automated LinkedIn Messaging & the Pros and Cons

Updated: Mar 16, 2022

800 million! That’s the number of members on LinkedIn as of 2022. Impressive right?

It's been growing steadily as the must-have channel in any outbound sales strategy and so have the opportunities and technologies out there to optimize it. Want to know more about automated LinkedIn messaging? Stay tuned…

What is LinkedIn Automation?

The Pros and Cons of Automated LinkedIn Messaging with OneShot

Designed to mimic human behavior, LinkedIn automation refers to any technology or toolset that aims to automate repeatable tasks on LinkedIn that you would otherwise have to perform manually.

They can automate almost any action on the platform, from scheduling and publishing content to visiting profiles and sending out connection requests.

According to their core function, they can be divided into a few categories:

  • Publishing and analytics tools – allow you to schedule and publish content, as well as track success, get suggestions, and create reports.

  • Connection tools – automate the process of sending connection requests and building rapport with prospects.

  • Lead generation tools – help you find potential prospects within your ideal customer profile.

  • Extractor tools – help you extract data from LinkedIn groups, post reactions, post comments, etc.

  • Activity automation tools – manufactures engagement by automatically posting and liking things on your connections’ profiles.

Disclaimer: Many of them fit into more than one category, but hopefully, this categorization will help you understand what you can accomplish with LinkedIn automation.

Why use LinkedIn Automation Tools?

Your outbound efforts may benefit from LinkedIn automation. When used properly (major alert!!!), it enables you to reach out to more prospects in less time, fueling up your lead generation.

These LinkedIn tools can help you find relevant leads and engage with them, send follow-ups and track success rates. This will ultimately improve your productivity.

What Exactly is Automated LinkedIn Messaging?

It's the practice of automating LinkedIn messages you send to connections, including connection request messages, prospecting messages, a follow up message on LinkedIn and any other type of message you may want to send on LinkedIn.

They fall under the connection tools category and, when used correctly, they can be a good addition to your outreach sales strategy.

Is Automated LinkedIn Messaging safe?

LinkedIn terms and conditions and how it will effect automated LinkedIn messages

Well, it really depends on how you use it. Using a third-party tool can go against LinkedIn’s Terms of Service, so doing it is inherently risky. If your account activity is deemed suspicious, for example, if you send an inhuman amount of connection requests, you’ll get a temporary ban, so essential it’s to use automated LinkedIn messaging tools in the right way.

The Pros and Cons of Automated LinkedIn Messaging

Weighing up the pros and cons of LinkedIn automated messaging

The Pros of LinkedIn Automated Messaging

A great way to save time

Having to manually write hundreds of personalized connection notes every month and tracking thousands of follow-ups is one of the most time-consuming tasks on an SDR’s job description.

A good automated LinkedIn Messaging tool will help you create message templates and set up a sales cadence that automatically triggers engagement and follow-ups. This way, you’ll have more time to prepare for your meetings and sell, which is the ultimate goal.

Consistency is key

Engaging with your prospects on a regular basis helps build rapport and having consistent and significant follow-ups will help you be memorable.

LinkedIn message automation can replicate this for you by setting up a series of touchpoints (sequences) aligned with the prospect’s feedback, goals, and timeline.

Want to know how to successfully approach prospects and conduct follow-ups? Click here to find out!

Great opportunity to do A/B testing

Testing different types of messages manually will take time. By using this type of technology, you’ll be able to test different templates and send them out to your prospects, something that you otherwise wouldn't be able to do using the native LinkedIn platform.


Automated LinkedIn messaging tools can be included in a multichannel prospecting strategy and integrated into the rest of your sales stack, ensuring that your LinkedIn output doesn't sit in a silo.

The Cons of Linkedin Message Automation

Risk of being banned

As mentioned before, excessive usage of third-party tools may put your account at risk of going against LinkedIn’s Terms of Service, which is why you should use automated LinkedIn messaging with parsimony. LinkedIn flags spammy behavior so make sure you only send around 100 connection requests per week.

It’s important to remember that if you personalize the connection notes on 100 requests, you’re more likely to have a meaningful reply from your prospects when compared to sending 200 requests with a generalized first message.

You only get one chance of making a good first impression. Make every connection count!

Forced personalization

The right automated LinkedIn messaging tools can allow you to hyper personalize your outreach. However, if you’re not using an intelligent enough technology, your connection messages and follow-ups might sound bizarre. Make sure that the tool you’re going for allows a more extensive personalization that goes beyond name and company tags.

It can compromise quality

If you choose a LinkedIn automation tool for messaging, don’t compromise on quality over quantity. Choose a solution that focuses on the quality of messaging rather than the number of touchpoints you can push out, best results can and must be achieved through respecting LinkedIn's connection limits.

LinkedIn shouldn't be treated like email, it's not a volume game, it's a value game. Use the connection limits to your advantage and find the balance with personalization.

It’s pricey

Automated LinkedIn messaging tools usually have an associated cost, besides normally working better with LinkedIn’s Sales Navigator, which is also a paid service. They can put a strain on your budget, so you should analyze the pros and cons, and choose a tool that can integrate your outreach strategy without feeling the need to completely automate it.

How to Incorporate Automated LinkedIn Messaging in Your Outreach Strategy


LinkedIn automation has fast become a hot topic in lead generation and can be a great asset to your outbound efforts, but as with everything in life, it should be approached wisely.

The first thing you should consider is that you should only automate tasks that don’t benefit from a human touch.

How to do it? With automated LinkedIn messaging you should always keep in mind that solid connections and meaningful conversations are a good way to generate leads. This means that personalization is key, so the tool you choose should focus on that.

You can get super high response rates on LinkedIn, so don't waste that opportunity by spamming them with email-style formal messages. Choose a software that allows you to send messages at intervals that mimic human actions. 20-25 messages per day is our suggestion.

Why? Because focusing on message volume misses the point of how buyers expect to be engaged on social media. Besides, bulk messaging will flag your activity and LinkedIn will suspend your account.

Use the connection request limit to your advantage! Focus on the quality of the messages and automate the rest to your advantage, such as setting up touchpoint sequences so you don’t need to worry about when and who you need to contact or engage with.

Bonus tip: Tier your prospect lists as a tactical way of automating. This will allow you to spend more time personalizing the top tier and maybe apply automation on the lower tiers.

Effective outreach messages need personalization, we can’t stress this enough and the right automated LinkedIn messaging tool should help you do just that. Humanizing automation is the future for outbound sales.

The Future of Automated LinkedIn Messaging

Storyboard of the levels of automated LinkedIn messaging

Most LinkedIn automation tools are evolving to increase personalization and even hyper personalize their message automation. Faster prospecting without losing a personal touch that makes the difference.

LinkedIn and email are two very different things. LinkedIn has strict rules which ensure that their users aren’t spammed. An approach based on quantity will most likely result in a banned account and the loss of a precious network.

The future of automated LinkedIn messaging should work with LinkedIn’s policies instead of against them. The outreach on LinkedIn needs to be focused on personalization, so both sales rep and buyer have a natural and enriching experience.

Hyper personalization is that future.

It uses artificial intelligence (AI) and machine learning to do your research for you, enhancing the overall buyer experience. It looks for patterns and provides you with information that would take you a long time to analyze.

What kind of information? AI can quickly look for similarities between you and your prospects as well as common interests. It can also take useful info in your prospects’ profiles like skills, biography, and recommendations, and create a solid message that will resonate with them.

Out Thoughts on Using Automated LinkedIn Messaging

Using an automated LinkedIn messaging tool focused on hyper-personalization will potentially help you have


A good conversation with your prospects is possible and having a LinkedIn automation tool to help build a solid rapport with them might just be that extra push you need.

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Are you interested in leveling up your prospecting? Read all about Linkedin Prospecting!

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