A Playbook for Cloud Enterprise Sales Professionals


Paul Melchiorre
Reading Time: 4 minutes



A Playbook for Cloud Enterprise Sales Professionals

Aurelien Mottier

CEO at Operatix

Paul Melchiorre

Operating Partner at Stripes

What does it take to be successful in Cloud Enterprise Sales?

How will the enterprise cloud sales market look like the next 5 to 10 years?

Recently on B2B Revenue Acceleration, we spoke with Paul Melchiorre, Operating Partner at Stripes and coauthor of the book Selling the Cloud, about the qualities of successful cloud sales professionals and the future of the market.

When Paul began his 25+ year career in the 1990s, systems applications and data processing was barely even a concept. He worked in numerous exciting companies, and by the dot-com era in the 2000s, Paul had already gotten swept up in a Silicon Valley startup that went public. 

After a stint as president of an operating company, Paul finally landed back in private equity, where he is now.

Let’s dive in!

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This is early stages of a much more rapid acceleration into enterprise cloud software, so it’s a great time to be in our business for sure.

Paul Melchiorre – Operating Partner at Stripes

Becoming a first-time author

Paul and his coauthor Mark Petruzzi recently launched ‘Selling the Cloud: A Playbook for Success in Cloud Software and Enterprise Sales.’

The motivation to begin writing grew out of Paul’s experiences of operating in different global venues with various large companies. 

Paul kept a notebook for key topics he thought might make it into a book someday.

Paul and Mark spend time on planning how to differentiate the book, to set it apart from the thousands of other sales process strategy books out there.


“We wanted to look at the key topics that can appeal to a very large audience, those that would be very new to sales or somebody who’s a 30+ year veteran like myself,” Paul said.

‘Selling the Cloud’ became a holistic playbook that everyone could get value from — not tactical or specialist, but the soft concepts that everyone needs.

Key topics in the book:

  • What are the characteristics of a successful sales professional?
  • Is sales a profession?
  • Mindset and trust — These are the things that make up this ideal sales professional. Are you good at these things? 
  • Could you be better at some of these topic areas?

Sales is a very broad profession, but when you get into enterprise, (especially cloud-based selling), it is a different level, like the Champions League in American football – it would be top tier.

You can’t specifically study enterprise selling at a university, unfortunately. The book is aimed at equipping this new set of salespeople who want to jumpstart into enterprise. 

“If we can accelerate that time to value, it makes a big impact on these companies, especially these small mid-sized companies that are really trying to grow,” Paul said. “This playbook is just so critical at this time.”

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Sales is a very broad profession, but when you get into enterprise, especially cloud-based selling, it just is a different level, kind of like the Champions League in football.

Paul Melchiorre – Operating Partner at Stripes

Essential traits of a cloud enterprise sales professional

Empathy, authenticity, creativity, and resilience: You can learn, refine, and perfect these elements to grow yourself and your success in cloud enterprise sales.As long as you have these characteristics and work to perfect them you can become a great salesperson.


You have to put yourself in your customers’ mindset in order to be effective. 

Even today when we aren’t selling face-to-face, you can still have empathy for the individual you’re selling to.

Pro tip: The individuals you sell to will move from company to company, so selling to an individual will connect you to numerous companies and contacts.


Authenticity is so important in this day and age, because the buyer is so much more advanced than they were years ago. 

Salespeople tend to understestimate the buyers, who through experience, have grown immensely in how effectively they operate.

A decade or so ago, the salesperson was a source of information to the client. Now, potential buyers may do more research online about your company than you do as the seller. Authenticity here is key.


Even with playbooks like Selling the Cloud, a sales professional still needs to be creative. 

Each company is different, the way they buy is unique, and the people in these different environments are separate individuals.

Regardless of sales methodologies and playbooks, you need a high EQ and to be creative for success in the complex world of selling.


Sales is not a nine-to-five job. That mindset will not lead you to any success in selling.

Sales can be challenging, and sometimes depressing in fact, you work every day but you don’t have success every day. 

Resilience differentiates the winners from the losers, especially in today’s sales climate.

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Resilience…If you think sales is a nine-to-five job, then you’re probably not going to be successful in any kind of selling.

Paul Melchiorre – Operating Partner at Stripes

The enterprise cloud sales market in the next 5 years

Let’s think first about the last 5 to 10 years, which 2020 just served to accelerate.

Everyone was heading online, some with more focus or urgency than others. 

In the business environment, large financial institutions, corporate companies, and global enterprises were moving on from their on-premise systems and transitioning into Cloud-based software, usually a division at a time.

The result of 2020 meant that we had more acceleration within 5 months than in the past 5 years. 

“This acceleration that was happening over the past decade or so, not only is going to happen over the next 5 or 10 years, but I believe that transition will bring a lot more opportunities to cloud-based companies,” Paul said.

Shortages will get worse if the supply side of supply and demand is fractured, and if the demand side also increases.

Education for enterprise sales people helps prepare a better supply in a market – especially where demand is going to continue to accelerate. The next 5 years will be dramatically more productive for cloud-based technology companies, AI and machine learning companies, data companies, security companies, and communication companies.

Big data, data integrity, data security, artificial intelligence, machine learning — all of which are on legacy applications will be disrupted by new cloud offerings coming in and taking over. 

“This is early stages of a much more rapid acceleration into enterprise cloud software, so it’s a great time to be in our business for sure,” Paul said.

Get in touch with Paul by email at paul@stripes.co, or learn from him in Selling the Cloud.

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About Operatix

Operatix is a Sales Acceleration company specialized in supporting B2B Software vendors to identify new revenue streams, increase qualified sales pipeline, and accelerate channel development across Europe and North America. Operatix has a wealth of experience in working with the biggest tech players worldwide as well as a multitude of emerging software vendors.

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