Automate part of your sales plan without sacrificing personalization

Define the limits of machine-generated actions and know when to switch from “cyborg” to human

Omar Benseddik
9 min readFeb 1, 2019
A robot can write names on your behalf

If you work in sales, or if your role involves a sales component, you will quickly realize that mundane and repetitive tasks are not little in quantity.

Having worked in both B2C (Business-to-Consumer) and B2B (Business-to-Business), I have often wound up doing a “monkey” task where my fingers did not really require much brainpower, except for the mechanical stimulus.

To give you an example, reaching out to 100 people with customized messages would consume a few hours from my time while automating the same outreach to 100 people would only take 5 minutes.

In this short piece, we will explore the solution to such manual sales tasks. 🔧

From “Sales seems fun” to “Urgh, feels numb typing similar messages 50 times in a row”

Use robots to keep smooth fingers

Let’s use an example. You work at a startup and plan to reach out to 500 professionals to convince them to use your solution, eventually converting them as your clients (this is called outbound sales).

You set up your CRM (Customer Relationship Management) tool to keep track of all the activities (calls, messages) and promise yourself that this time you will be disciplined enough to record all your leads, add notes and update the system once in a while.

Heh, sure. Do this alone and you’ll soon be stuck with not only an incomplete CRM, but a Google Sheet, and if you are old school, a notebook.

You’ve now reached out to 500 leads, welcome to the whirlwind! Some showed interest, you’ve scheduled calls and demos and even managed to convert a few to actual clients (this is awesome, bravo to you).

Despite spending plenty of time researching ideal clients and drafting hundreds of personalized messages (you know generic approaches sucks), you decide to re-do what you’ve done, get another handful of clients and keep doing so until you accumulate a certain set of clients (hence, a certain amount of $).

Easy, huh? Nope, and here is why: once you get those clients, it does not mean you are done with the sale. You’ve in fact just scratched the surface once the contract is signed. 🔏

The clients you got still need you. They have questions, they need advice, they have doubts, they have remarks, they have suggestions and most importantly, they need to have someone to talk to. And that person is you.

But you, are busy trying to get new clients, yet, realize that you cannot let those clients hanging on. What then is the solution to keep reaching out to new prospects, and being able to manage your current clientele?

Automation. *holy voice chanting Auuu-toooo-maaa-tioooon*

“I’ll automate the mundane sales tasks” — know where to set limits for automation

Robots are your friends — think of fridges

I recall the time I challenged myself to contact 100 people on LinkedIn with a personal touch within a single day. I managed to complete this tedious challenge but was exhausted, felt that I had spent the day doing a dull task, and understood the need to robotize part of my workflow.

There are plenty of steps in sales: prospecting, reaching out, scheduling calls, taking the calls, respond to inquiries, negotiate with the relevant stakeholders, do a demo, and so on. The boring ones (and undeniably, time-consuming) are writing messages on LinkedIn, writing outreach e-mails, finding e-mail addresses, schedule calls, and tracking performance.

Clearly, automating the whole sales activity is not doable (yet) in early-stage SaaS (Software-as-a-Service)/B2B. Humans need other humans to communicate with, and emotional intelligence, negotiation skills, and personal touch are key elements to succeed in this context.

Writing 100 messages on LinkedIn just to perhaps grab the attention of a person, to perhaps get in a call, to perhaps schedule a demo, to perhaps close a deal, is a time-consuming activity.

You may be excited at the beginning, especially if you are new to it, and think that you will have the patience to keep grinding, but you’ll eventually be tired of the “rejection” (in fact, you need a really high tolerance towards that), and executing boring, repetitive and humdrum tasks.

All of these can be automated. And just because you automate, does not mean you have to be generic. You can keep your style, personalize your approach and still be laser-sharp precise when you reach out to potential clients.

How? By creating small buckets of potential clients, and separate those by industry or context, to reach out to them with relevant messages. For example, you could have a bucket of 10 clients in the education sector, a bucket with 8 clients in the cryptocurrency sector and a bucket of 10 companies that recently got funded. 💰

“Hello [Name]”, “Hello [Name]”, “Hello [Name]” and to infinity and beyond

A robot substitutes humans

Let’s use an example. A new ranking of the “top 50 startups to work for in Germany” made its appearance online, is being shared heavily on social media and creates a certain “buzz”. You skim through the list and realize that 30 out of those 50 startups are potential clients.

Here’s where automation comes into place. If you decide to reach out to these people on LinkedIn, you could use a tool such as Orca to automate messages. The first step would be to find those people on LinkedIn, copy their profile URLs on a Google Sheet or Excel, convert it to a CSV and upload it to the automation tool.

Moving on, you would write a short message opener that relates to the Top 50 Ranking and suggest to the message’s recipient to have a chat with you.

Did you see what we’ve just done? We’ve just written a very personalized message and managed to automate it.

To avoid coming out of the blue on LinkedIn, you could set up Orca to “look at the profile” a couple of times before sending that message. When you click on someone’s profile, that person receives a notification saying that you’ve seen their profile. That feature is interesting (and creepy) as it warms up your lead before you get in touch (unless they have anonymous settings, meaning no notification is sent when they see a profile, and no notification is received when their profile is seen).

Moving on, when someone accepts your LinkedIn invite, you’ll be more likely to appear on that person’s feed (compared to any other person).

Therefore, you should leverage that by writing meaningful posts (not one of those cheesy ones, even though it seems to work well) or share insightful content and comment on it. That way you will appear in their radar, improve the image you give of yourself and give them the opportunity to engage.

Though, it is important to understand that using such third-party tool can be risky. If you read LinkedIn’s End User Agreement, (Section 8, Subset 8.2 “Dont’s”, letter “m”) it clearly states:

“You agree that you will not use bots or other automated methods to access the Services, add or download contacts, send or redirect messages.)”

If LinkedIn catches you using the bot, your account may get suspended (see my edit at the end of the article). 😤

“Hello, I got in touch with you on LinkedIn but it seems like my message didn’t reach” — write that 300 times and your fingers will despise you

I still don’t know what GDPR is tbh 😂

Do we stop at LinkedIn? Nah. That is just the beginning. Once you reach out to someone, you can shift channels and start reaching out via e-mail.

Manually? Nah. Get the robot to do it for you this time again, and you’ll be able to schedule follow-ups (got to, if you want a response) and measure your performance (open rate, response rate, top subject lines, and so on).

Want a tool? Frankly, I am still thinking of which one to use. I am inclined to use Reply, but have recently discovered Snov, and I am evaluating both. At the end of the day, the idea is to use one of these tools to look for e-mails on your behalf, send e-mails and follow-ups, and measure your success rate.

If you are in Germany (or any other EU country), you have to make sure that what you are doing is GDPR-compliant, as you may face penalties. Also, use the right tools to achieve your goals. Do not use MailChimp to automate cold outreach e-mails, as they are not meant for that purpose. 🐒

“Is Monday 9:45 good for you?”, “Well, I’d rather do Tuesday 15:45”

A robot can decide on timing on your behalf

One very important aspect to highlight, in this strategy, is that once you have received a response, cut the robot part and interact humanly. However, that does not mean that automation stops absolutely.

Once you receive a response and you start to chat, you’ll probably end up having a call, and you’ll have to schedule it.

To avoid back-and-forth e-mails, use a tool such as Calendly, which synchronizes with your calendar and offers pre-validated time slots to your contact. 👩‍💻

Send “Hello Stefanie” and realize 0.2 seconds later that the person’s name is Mustapha

His name is not Stefanie, and you feel ashamed after sending the wrong name

Be careful with the goofs, there are many you might do with automation:

  • Inserting the code snippet instead of the name: you can add the recipient’s name with a code snippet. Be sure to test it to avoid sending hundreds of people “Hello &[(First_Name)]&”.
  • Contacting one of your current clients: let’s say Hussam from Cookies Munchies is your client. If he receives an automated message suggesting an intro chat, Hussam will probably be turned off by your lack of professionalism and attention to detail. 🍪
  • Contacting one of your warm leads: if one of your automated messages gets a lead to respond, that lead should no longer receive automated messages. Be wary if you use multiple channels (e.g. your lead responds on LinkedIn, yet will receive automated e-mails.)

“You automate tasks, so you don’t care about who you speak with.”

Using tools does not de-humanize the sales process

At this stage, you probably think I am some sort of sneaky villain who tries to maximize output with minimal effort and pre-meditated strategy.

The second part is true, but the first is not.

I feel sales has a bad connotation in the majority of people’s minds, and that is probably because of the stereotypical image of the salesperson in a suit who would be fine selling ice to an Eskimo (a great example of a non-existent value transaction from the buyer’s perspective).

I perceive sales as an enabling function where, if you have the luxury to work for a company that provides valuable products or services, improves the clients’ productivity and delivered value.

To sum it up, if you feel stuck doing manual sales tasks, automate them, don’t sacrifice your style and focus on more brain-intensive activities. 🧠

I consistently publish one article per month (for real, it’s not one of those New Year’s resolutions).

You can follow the Medium account to stay tuned. 🦏

Edit 2nd March 2019: Hello reader. I have published this content on the 1st of February 2019. A month later, my LinkedIn account got restricted, but I got it back after submitting an ID. Be careful with the automation :) You don’t want to be left out of LinkedIn (unless you have $50m in your account, ofc).