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From Cold Calls to AI: A Sales Leader's Guide to Confidence, Connection, and Continual Learning -- Tom Bertrand, Reachdesk

November 7, 2023

Arjun Krisna


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In the world of sales, success often depends on a unique blend of resilience, curiosity, and adaptability.

Tom Bertrand, embodies these qualities and shares his insights in this candid interview.

His journey from overcoming sales anxiety to becoming a team lead at Reachdesk is a testament to the power of persistence and personal growth in this competitive field.

In this interview, Tom provides valuable advice, stories, and recommendations for anyone looking to thrive in the dynamic landscape of sales.

Also, don't forget to check out our previous blog, where we put together a list of 7 must-follow B2B sales leaders to nail your cold outreach.

Without any more delay, let's dive in.

What are some of the highlights of your career so far?

The highlights of my career have been overcoming the anxiety of being in sales, picking up the phone, and gaining the confidence to cold call. Joining Reachdesk and making my first commission has been a significant achievement.

If you could write a letter to yourself from now to the beginning of your sales career, what would it say?

The letter would emphasize trusting the sales process, having fun, not taking it too seriously, and being more human in interactions. It would encourage a positive and enjoyable approach to sales.

What is the most surprising thing that you've learned from a customer?

The most surprising thing has been how receptive people can be when you've done your research on the prospect. Demonstrating knowledge about their company and persona can lead to better and more productive conversations.

What's your most unforgettable behind-the-scenes sales story that no one knows?

The most unforgettable experiences involve being human in sales, having fun, and making the cold call process enjoyable for both the sales rep and the prospect. Adding humour and light-heartedness can lead to better connections.

If you could have a mega billboard and share just one sales tip with the world, what would it say?

The billboard would promote learning as much as possible. There is a wealth of knowledge available in podcasts, LinkedIn influencers, and other resources. Continuously educate yourself to improve your sales skills.

What is the role of AI in sales currently, and how do you think it'll evolve the role of a sales rep?

AI is transforming sales by improving personalization, speeding up tasks like email composition, and even assisting in call responses. It's expected to make sales more efficient and personalized, benefiting both sales reps and prospects.

What sales resources do you recommend for upcoming sellers?

I recommend podcasts like "The Diary Of A CEO" for mental stimulation and "33 CXOs" by John McMahon, especially if you want to make the jump into an AE role.

Tom's words offer a glimpse into the evolving world of sales, where embracing AI, personalization, and continuous learning are key to success.

We hope you've found his experiences and insights as valuable as we have.

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