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10 Cold Call Lessons from Sheriff Shahen

(after making >100k Cold Calls)

Chris Ritson

15 Dec 2023

3 mins

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There aren’t many people who have made over 100k cold calls in the world. 

But I’m delighted to be introducing everyone to Sheriff Shahen, Enterprise SDR @ Deel (the fastest growing tech startup ever going from $50M ARR to $100M in 3 months). 

Sheriff has built a personal brand on the back of his Cold Calling expertise and I thought his learnings would be helpful to share with everyone here this week. 

In this newsletter, I’ll tell you Sheriffs story and give you his top 10 lessons from 7 years in sales and making >100k Cold Calls. 

Lets dive in. 

His Story:
  • 7 years ago, Sheriff started as a telemarketer, doing 200-300 cold calls a day selling lottery tickets. 

  • Studied Sales and got himself a bachelor’s degree in International Sales & Marketing. 

  • Has made over 100,000 cold calls for the past 7 years selling into both B2C & B2B worlds. 

  • He has never left Sales and is currently an Enterprise SDR for Deel, the fastest growing SaaS company in the world.

Lesson #1: 

❌ Mastery in cold calling is a talent. 

✅ Mastery in cold calling is developed. 

No-one is born with the natural ability to cold call, it’s learnt over time so commit to learning the skill. The results will follow. 

Lesson #2: 

❌ Know the product features very well. 

✅ Know the problems you solve better. 

Product knowledge is great and all but prospects care about their problems first and foremost so double down on learning them deeply. If you’re onboarding programme doesn’t double down on problems it’s not fit for purpose. 

Lesson #3: 

❌ Be polite, ask if you’re interrupting with your call.

✅ You’re always interrupting, let them quickly know why..

Don’t ask ‘is now a good time? Instead, say ‘the reason I’m calling is X’. Be concise and don’t waste anytime getting to the point of why you’re on the other end of the phone. 

Lesson #4: 

❌ Silence is very awkward. 

✅ Silence is a powerful tool. 

You will naturally feel awkward when no-one is saying anything and want to fill in the gaps by monologuing. It’s okay to wait it out and see how your prospect responds. 

Lesson #5: 

❌ Cold Call success is booking a meeting. 

✅ Cold Call success is having a conversation. 

If you call someone out of the blue, interrupt their busy day and manage to have a conversation, that’s a success in itself. Booking a meeting is different as this comes down to whether there is a fit or not. Simply put, you need to start the conversation first - win. Then if you book the meeting afterwards that’s another win. 

Lesson #6: 

❌ Read your script word for word every time. 

✅ Have a talk-track and adapt to your prospects. 

Knowing your talk track is very important at the top of calls so you can focus on tonality but you will have to adapt the problems you are speaking to from persona to persona. For example a Head of HR (if that’s who you sell to) will care about different things to a CHRO. You need to slightly adapt the words you use to that which is why knowing their problems deeply is important. 

Lesson #7: 

❌ Rejections are personal. 

✅ Rejections are an inevitable part of the process. 

The people you call do NOT know you, therefore they do NOT trust you. Striving to win every time is important but accepting you can’t win every time is also part of the process to mastery. 

Lesson #8: 

❌ Use industry jargon to sound knowledgeable. 

✅ Adapt your language to your prospects. 

Buzzwords are not helpful for prospects. Using words like ‘synergy, optimise, scale’ confuses your prospects as they don’t know what you really mean. Be very prescriptive and ‘‘dumb down’’ your language so it’s very easy to understand. 

Lesson #9: 

❌ My pitch needs to be perfect. 

✅ My tonality needs to be perfect. 

Tone accounts for >80% of communication on the telephone. Words (aka your pitch) accounts for the rest. Lean into your tone and what makes the biggest difference. 

Lesson #10: 

❌ ABC (Always be Closing). 

✅ ABQ (Always be Qualifying). 

The job isn’t to force the next step to happen against your prospects will. It’s to work out if you can help them with a problem they have. Only when you’ve found a challenge you can help with should you be booking a meeting. 

So there you are folks, 10 lessons from >100k dials. You can follow Sheriff on LinkedIn or you can book him for 1:1 Cold Calling sessions, just message him for more details. 


Well, thats everything this week, I hope you liked the episode, I will be doing more featured articles of peoples stories as this newsletter evolves in 2024. 

If there is anyone you would specifically like me to interview let me know by responding to this email. 

PS. Please forward this newsletter to your teammates if they also Cold Call. 

Good luck folks!!

New Product Update: 

Here’s a sneak peak at what I’ve been working on this week and will be launching in January….(yes, its a digital course).

Weekly Send-Off:

I hope you all have a great weekend, here’s my tweet of the week:

Until next Friday at 1.05pm, au revoir from me, Bridge, and Isaac 🙂

Whenever you’re ready, here are 2 ways I can help you (both go on sale next week): 

The next leader bootcamp starts in January. Join 50+ others and save your seat here

The next bootcamp starts January 22nd. Join 80+ others and save your seat here.

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© 2024 Chris Ritson. All right reserved.

© 2024 Chris Ritson. All right reserved.