The Prospecting Masterclass. Ep.16

Hi there Croners! We’re back with the 16th episode of “The Prospecting Masterclass”, we’ve come a long way, haven’t we?

Today’s guest is a force of nature, with an incredible job experience in some of the biggest and best companies in the field. His quick rise in the business didn’t stop him from gaining consciousness of both technology and human interaction.

We’re excited to have with us Alessandro Raponi, Co-Founder @ We Deal Saas and much much more who will be sharing his amazing journey across Europe and current projects.

Find his interview below. Thanks Alessandro!

Let’s dive right into this fresh interview, enjoy reading!

1) Hi Alessandro, can you tell us about yourself and your experience in B2B Sales?

Sales is the only profession I have ever done. I started my career in B2B sales 10 years ago when I joined Rocket Internet in Berlin as Global Venture Developer for one of its startups. After failing the interview process at Google (probably for the best) I still managed to move to Dublin joining the FutureForce program of Salesforce, moving up the sales ladder quickly. Salesforce is the best sales school there is out there. There is no other tech company that can match its sales operations and efficient processes.

After surviving 6 years of monthly targets, a very competitive environment and one President Club, I moved back to Milan entering the Cybersecurity space with Splunk to then circle back to Google where I managed the GTM for Google Cloud’s Security portfolio in Italy.

In 2023 I decided to quit the corporate world and now I lead my own project with We Deal SaaS where I help companies buy software consciously. At the same time, I’m launching one of the first European Sales Agencies: Raascals, whose aim is the accelerating penetration of new markets in the EU for tech companies who are looking to scale up.


2) How would you describe yourself if you could only use 5 words?

I could actually use an acronym: KaaS = Kindness as a Service

3) What are the most difficult challenges you have faced regarding Prospecting and Outbound Sales in your past and current professional experiences? How did you solve them?

The hardest part of a sales job is doing outbound. No one is mentally prepared for receiving so many NOs

Back in the day, Cold Calling was the main way to go, I remember spending days calling companies and fighting gatekeepers in order to get to speak with the right person in the company or testing business emails with MailTester. 

What made the difference back then were 2 key attributes: resilience and positive attitude.

4) How do you see B2B outbound sales changing in the next 12 months? What challenges and trends do you anticipate?

Today, the challenges I faced don’t exist anymore. There are no more gatekeepers as people are increasingly working remotely and, frankly, calling the office is useless. Now the rise of new prospecting technologies like Lusha, Lemlist or Apollo, to name a few, gets you access to the right email and phone number with 1 click, which makes it very easy to reach your ideal target. 

However, now you have to learn how to stand out among the hundreds of emails/calls that a CXO gets daily and that’s not an easy task. Personalization is key. AI is helping and there are tools like that help you personalize at scale. 

But as AI is becoming mainstream, soon that won’t be enough anymore. The speed at which technology is disrupting every profession, sales included, makes it hard for salespeople to stay relevant and be heard. Creativity will be the key to success.

5) What advice would you give to someone starting today as an SDR?

Have patience, don’t rush it. Put yourself out there in creative ways and don’t be afraid of making mistakes. Prioritize delivery and execution over a polished and perfect message. Be resilient. And enjoy the journey, learning from every interaction you make along the way.

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