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Why You Fail At LinkedIn Cold Outreach And How To Fix It

linkedin cold outreach

Go from 0 to $100,000 MRR using only LinkedIn cold outreach

Generating B2B leads is time-consuming and draining. Anyone who tells you otherwise either has an established industry track record already or has not done lead generation themselves. 

68% of marketers still struggle with lead generation (CSO Insights) Furthermore, only 7% of salespeople surveyed by Hubspot said leads they received from marketing were very high quality. 

If you are a B2B marketer in the software or even Crypto industry, you may face one or a few of these challenges

  • You generate many leads, but only a small percentage of them convert
  • You have no other reliable source of lead generation aside from running digital ads
  • The cost of acquiring quality leads is high, as it involves sponsoring expensive conferences or writing reports
  • If you work in a startup, potential customers rather work with well-known competitors instead  
  • The marketing budget is small, as it is difficult (or almost impossible) to justify the returns from your marketing spend

The great news is that many marketers face the same problems as you. The bad news? If you continue in this direction, you will never stand out from the rest. 

Before we get into what you can do to generate quality leads at a low cost, let us dive into why you and many marketing professionals face the same issues. 

“Best marketing practices” likely do not apply to you 

We can find answers to almost any question we have on the internet. However, this does not mean that every or any of these answers fit your particular set of circumstances. 

This is especially so when it comes to marketing tech products. Take the classic marketing advice of “Content is King”. Your competitor is a company with ten times your marketing budget and can write hundred high-quality, search-friendly blog posts in six months. Their inbound marketing leads increased by five times over the past year.

In comparison, your marketing budget only allows you to write twelve blog posts in the same time period. Assuming both companies write blog posts of similar quality with the same distribution channels, your inbound marketing leads only increase by 20%. 

Does this mean that content marketing is not an effective lead generation tactic? Absolutely not. In this case, it only means that following marketing best practices without any changes to fit your context is ineffective.   

Create A Marketing Strategy That Only Applies To You Right Now

Marketing best practices do not work most of the time, as no two companies or products are ever the same. So what can you do and where do you start? Before we get started on lead generation, we need to have a crystal clear answer to this question. 

If you have tried various marketing channels and activities with little success, you are likely to have a foundational problem. Often, we see results when we spend enough on digital marketing. This leads us to focus on getting short-term results to hit our KPIs, without thinking of a marketing strategy, where each marketing action builds on the last one.

While there is no one size fits all approach, these are what you need to build a marketing strategy that fits your company right now, taking into account the resources at your disposal. 

Start With A Marketing Audit 

Look at your previous marketing efforts from a macro perspective. This involves doing a SWOT and 4Ps analysis of your product against your competitors. It may sound a little too simplistic in today’s complex business environment, but it gives us a good start.

More importantly, when doing a SWOT analysis, be brutal in challenging the inherent assumptions you make. Focus on the “Weakness” and “Threats” portion of the analysis, as that is where you get the most value. 

Some common assumptions that startups make when doing a SWOT analysis

  • “We are innovative”-> How are your products and processes different from your competitors? More importantly, do these differences matter to your customers?
  • “Our people are the best in the industry”-> Do you have a way to benchmark this?
  • “Product feature xx solves many of customer’s problems”-> Do customers really come back for that particular product feature, or do they use your product in another way   

Prove or disprove these assumptions by interviewing your team, current prospects and customers for a rock-solid understanding of your company’s position. It will be tedious and time-consuming, but well worth it when you generate your first 100 B2B leads.

Draft a sales playbook to get everyone aligned 

Everyone on the sales and marketing team needs to know exactly who they are selling to, what pain points the customer has and the selling point of the product relative to competitors. This may seem obvious, but misalignment between sales and marketing happens more often than we think. 

b2b sales playbook

When the marketing team generates leads that the sales team does not agree with, it is a recipe for disaster. To effectively generate quality leads, the marketing team needs to draft a sales playbook, which should minimally consist of the following.

Buyer Persona 

A buyer persona is a detailed outline of your ideal customer, someone who is willing and able to buy your product. You can get this information by interviewing current customers or even from your daily interactions with them. 

Some key information that needs to be included in the buyer persona 

  • Size of the company-> Are we targeting MNCs or SMEs?
  • Job title of the prospect
  • Their KPIs-> What will make them miss their KPIs and how does your product help them?
  • Daily work responsibilities 
  • Where do they go to find answers when they meet problems in their role?

Sales Value Proposition  

Your prospect must be clear on what makes you different from your competitors. Otherwise, they will not buy from you, as you have not answered the “Why us” and “Why now” questions. 

If you are a startup, these are some common differentiators you can offer 

  • Customization: “We customize our offerings just for you, as we can give you more attention than bigger competitors in the market” 
  • The disruptor in the market: “As big companies become complacent, we see many problems in the industry that can be solved with our solution” 
  • Best solution in a particular niche: “We solve only one problem and we do it the best”

Create a cheat sheet outlining the company’s value proposition and share it internally. Repurpose the content for different selling situations, such as an elevator pitch and what your sales representatives can post on LinkedIn. 

Objection Handling Sheet

You and your team will always face objections. There will always be some objections that get raised more often than others. Preparing for these objections before each meeting will give you a better chance of closing the deal.

Map out the common objections by persona and each stage of the sales cycle. Test the responses for each common objection and measure the effectiveness. 

An example of a common objection will be the prospect’s lack of budget. Prepare a few different responses similar to the image above that your sales team can use when faced with this objection. 

Successful Case Studies Build Trust

Last but not least, build different case studies where you have successfully helped customers solve their problems. This can be in the form of a one-pager, “testimonial” page on your website or even video interviews of your customers. 

Social proof will always be one of the most effective methods to close any prospect.

LinkedIn Cold Outreach Still Works (If Done Properly)

You have built a solid marketing strategy and laid the foundation for long-term lead generation success. However, you are only halfway there! Choosing the right channel and methods to execute will make or break your lead generation results.

Unless you have a giant marketing budget, you should always start with LinkedIn cold outreach as your first lead generation channel. Contrary to some belief, LinkedIn cold outreach is still very much a viable lead generation option and it gives a predictable and reliable stream of leads if executed properly. 

Create a list of qualified contacts

After you have created your buyer personas, now is the time to find their contact details and reach out to them with the messaging you have prepared for each profile.

To save time, scrap the relevant list of LinkedIn contacts using software such as Phantombuster.  Filter the LinkedIn search results according to your buyer persona and export the list of contacts into an excel sheet.  

For example, if you are selling software that helps with lead generation, marketing managers may be one of your buyer personas. Simply search “marketing manager” on LinkedIn and filter the specific companies you want to reach out to. 

Linkedin lead generation

Paste the URL of this search result into Phantombuster (or any scraper you use) and export the contacts into an excel spreadsheet. 

At this point, many LinkedIn cold outreach guides will ask you to create a standard messaging template to use on all contacts and automate your outreach, by having the software send your messages for you. 

Do not do this, especially if you are serious about generating solid leads for your business. 

Think about it- how will you feel if someone sends you a message the second you accept their connection request? Or if you receive a generic message that has little to no relevance to your profile and has clearly been used on other prospects as well? 

This is what it feels when someone sends you an automated message. 

Balancing between building relationships and scaling

While personalizing and manually sending out connection requests brings the best results, it is too time-consuming to scale. To achieve this balance, create different messaging templates for each buyer persona, based on the pain points they experience. 

Before sending out a connection request, add a line or two to your messaging template that shows you actually read the person’s profile. 

Agree with an article she just posted? Give an opinion on it! Both of you worked at the same company before? Let her know! This is how the other party knows she is more than a stepping stone for you to hit your sales target.

When you know that someone actually took the time to learn about you before prospecting, you are more inclined to respond to them, even if you are not ready to buy. 

Getting from the first message to a sales call 

In my opinion, the marketing team is doing its job for lead generation when a prospect from the buyer persona agrees to take a sales call. Ideally, the prospect knows about the company’s offering and the problems they are looking to solve before the call. 

That’s all the marketing team should be doing to generate leads. Nothing more, nothing less. 

Assuming a prospect has not heard of your company before, a typical lead generation process will look like this. 

  1. You send a connection request with a note
  2. Your connection request is accepted and you send an introductory message 
  3. Ask if your prospect would like to have a call 
  4. If your prospect declines, ask if you can send some materials for future reference to his email
  5. Follow-up where appropriate

Let’s go through each step in detail 

Sending the connection request

The only goal at this step is for your prospect to accept your connection request. You are not making a sale at this point, nor are you introducing yourself and your company. 

At this step, simply share that you are sending a connection request because your prospect is in the same industry. Even better if you can comment one or two sentences on a recent post from your prospect in your note. 

Crafting an introductory message after your request is accepted 

Congrats! Your connection request has been accepted! However, this does not mean you should send a sales message yet. Most sales representatives start to copy and paste from a template and ask a prospect to book their time via their calendly link. 

That is a HUGE turn-off. 

Linkedin cold outreach
Actual pitches I received from the same person

Remember: No one wants to feel that they are just a number for you to hit your sales target. To get a more favorable response, all you need to do is to focus on introducing yourself and your company in the clearest and most concise way in your first message.  

There are many ways to craft the introductory message depending on your style, but your message should contain the following 

  • Why you are reaching out to your prospect specifically (what are the pain points based on the buyer persona?)
  • The solution you are offering and how it relates to their pain point, in 2-3 sentences
  • Ask if this is something they are interested in exploring right now

There is no exact format for this, but if you have no idea where to start, a standard template will be as follows

Hi [prospect],

Thanks for connecting!

I am reaching out to you specifically as I think that [pain point #1] and [pain point #2] are key aspects of your role in [company + job title]

At [Your company name + website] we offer [solution + unique selling point}

Would using [solution to solve pain point] be something you are looking at?


[Your Name]

Asking for an introductory call 

At this point, you are unlikely to receive a straight “yes” from your prospect and that’s perfectly normal! Rather, you will most likely (or have already) received these responses

  • “Can you please share more information”
  • “Not interested, thank you” 
  • “We have our own solution already”
  • “We are using (competitor name) currently”
  • No response after reading your message 

Use your objection handling sheet to give the best reply. Your objective is to give your prospect a reason to jump on a call with you. 

Pro-tip: Do not ask your prospect to book a time with you via your calendly link. There is a good chance that they will forget to book a time slot or ghost you. 

Handle Rejection The Right Way

Getting rejected is the norm, especially when doing Linkedin cold outreach. While some people may advise you to keep following up until you get an answer, I do not advocate that. 

There are three groups of people who you will reach out to. First, the prospects actively searching for a solution similar to your offering. As they are already 90% sold, you will not have any issues with them. 

The second group involves the prospects who will never buy from you, even if they fit your buyer persona. Either the company has already built the product in-house or they just do not believe in your product. No matter how good a discount you give them or how great a marketing campaign you run, they will never be sold.

This then leaves us with the last group, people who are still on the fence. You should be spending time and effort handling the objections from this group, without closing the door on future opportunities. 

What does this mean in practice? In short, know when to follow up, when to settle for a “smaller win” like adding a contact to your newsletter and when to stop following up completely. Badgering a prospect who is on the fence with multiple follow-ups, despite no replies, almost guarantees losing the sale. 

As these follow-ups are more of an art than a science, there is no “best practice” template for what smaller wins to ask for and when to stop following up completely. You will need to rely on your own intuition for this.   

Scaling From 0 To 100 B2B Leads Through LinkedIn Cold Outreach

So far, we have covered how you can create a marketing strategy that works for you at the current stage of your business. We then went into detail on how exactly you can do LinkedIn cold outreach effectively. Similar to your marketing strategy, your approach to each phase of lead generation will be different.

Laying Out The Assumptions

No two companies are ever the same. Generating 100 B2B leads may take one company just a month and another company a full year if not more. Before we go into the specific actions you can take for each phase of your lead generation, let us lay out the assumptions below

  • We define a “Lead” as a prospect that meets your buyer persona and has agreed to join you on a sales call 
  • We are selling a software product that costs between $10,000 – $100,000 a year, with only paid trials available. Prospects do not have the option of a free trials
  • As more leads are secured, more revenue will be put into the marketing budget for LinkedIn cold outreach. We start with a budget of zero  
  • You have crafted a marketing strategy based on what was shared above. The buyer persona, value proposition and objection handling have been crafted 
  • We set a target of generating 100 leads within 3 months 

With that out of the way, let’s get right into it!

Starting From Scratch 

The first 10 Leads will be the hardest to secure, especially if you do not have any reputation or contacts in your target industry. To get started, scrap the list of LinkedIn contacts that meet your buyer persona. 

Manually send out 75-100 connection requests a week (LinkedIn caps the number of connection requests to 100 a week) The key is to send the bulk of your connections at the start of the week, so that your follow-ups are more likely to get a response before the end of the week. 

Do not send connection requests on the weekends. Even if you do, your prospect will likely accept your connection request on a working day. 

Always send a message to prospects who accept your connection request within 24 hours. For prospects who do not reply to your follow-up message after reading it, only follow up 24-48 hours later with one message only. Do not badger your prospect with a chain of messages. Limit the number of follow-up messages to two. 

With time, you will secure your first 10 B2B leads.

Generating The Next 40 Leads

Congratulations! You have completed the hardest step of generating your first 10 leads. The next step is to secure 50 leads in total. To start scaling your outreach, you will need to tap on the network you built and start positioning yourself as a thought leader in your space. 

Reach out to your current prospects and ask if they know of anyone who will benefit from your solution. Give them a reason for helping you- it may be referring them to someone they may benefit from meeting or just an introduction to a resource. Often, prospects will know of contacts in their industry who have the same pain points as them. 

You will be surprised by how many contacts you can gather just by asking each prospect and their contact if they know of someone who will benefit from your solution! 

Next, start positioning yourself as a thought leader in your industry by posting useful commentary regularly. Some useful content can be your learnings from interacting with prospects in the industry or just commenting on the latest news from your industry. 

Post this content on all your social media accounts, industry forums, and even as guest posts on select publications! Remember our assumption about spending revenue earned from lead generation on marketing? Start outsourcing content creation and distribution to freelance writers so that you have the bandwidth to focus on your LinkedIn cold outreach.   

Providing useful commentary will give you the credibility for prospects to trust you. Contacts you have reached out to will see that you are a thought leader in your field when they research your profile.

Tapping on the network you built and positioning yourself as a thought leader will bring in the next 40 B2B leads. 

Getting To 100 B2B Leads

At this stage, you have a clear strategy for lead generation. You know exactly who will buy from you, the selling point of your solution and how to best communicate it to prospects. You have momentum by doing LinkedIn cold outreach each day and are starting to become a thought leader in your industry. 

To finally reach the goal of securing 100 B2B leads in 3 months, it is not enough to rely solely on yourself now. Start getting your team involved in the lead generation to really scale! 

Transfer knowledge from your winning LinkedIn cold outreach playbook to your team. Whether they are a software developer or product manager, everyone in your company should be able to sell the product.  

What if the team does not have enough time? Or what if there is strong resistance from colleagues outside of sales and marketing?

This is why internal marketing is so important and convincing management that involving the entire company in lead generation efforts is ironically the most efficient way to scale. Getting departments outside of marketing to help with lead generation does not need to be a huge task from the start. 

This can be in the form of outreach sprints once every bi-weekly or monthly, where your colleagues execute your sales playbook. 

Consider matching prospects based on your colleague’s functional role. For example, if your colleague is a software developer, provide him with a list of prospects who are tech leads, if they are in your buyer persona. This will help him better understand the pain points of customers and better pitch to the prospect from a technical perspective as well.  

If it is difficult to get buy-in for lead generation in your company, hire freelancers or a callout agency to run your sales playbook. This will get you to 100 B2B leads in 3 months.

How To Scale To 1,000 B2B Leads? 

I have just shared with you a proven and effective way to generate 100 B2B leads from LinkedIn cold outreach alone. However, why be satisfied with only 100 leads when you can capture 1,000 quality leads for your company?

Interested in finding out how? Let’s have a chat!

Contact me here or send an email to

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