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David Perry: Game of Sales; Lessons Learned Working at Adobe, Amazon, Google and IBM

Sales as profession

I soon realized that companies of all types and sizes in all industries are on the sales table. It’s a profession that provides ultimate marketability.

A career in sales means much more than having a highly marketable skillset. It also means that you’re going to have access to some of the most incredible experiences the world has to offer, especially if you choose to work in enterprise technology sales.

Top enterprise salespeople are teammates, consultants, analysts, product experts, project managers and leaders. How do you stack up in these areas?

Getting a handle on the industry landscape is one of the most important things you can do to take your sales career to the next level. Technology is another key aspect of your knowledge arsenal. It’s eating the world, as we know it.

IBM provided me with an incredible education into one of the most complex and matrixed organizations in the world. I saw, firsthand, how a consulting and systems integration company could implement a tip of the arrow approach to the addressable market and increase opportunity size.

One of the ways this works is a consulting team identifies a major opportunity and passes it along to the most appropriate, capable sales team or business unit within the organization. That team then assembles the ideal bundle of products and services (referred to as the solution) to meet the specific needs of the client early in the sales process. The solution is then supported by a full assessment, business case and implementation plan. The tip of the arrow in such a scenario refers to the strategy consulting team that kicked off the process. They engage the client at senior levels to provide an entry point for the company to form a partnership with them.

IBM, Google, Amazon and Adobe

My IBM experience showed me how there are always multiple decision makers within large organizations that you need to win over to get a deal done.

Unlike Google, Amazon creates the future around their core tenants and/or beliefs about things that won’t change.

Google, Amazon and IBM are names that are immediately recognizable as having a massive technological impact. Don’t underestimate the impact of Adobe, however, in your efforts to ramp up on technological trends and industry influence. Adobe’s lesser-known division called Digital Experience covers everything from digital analytics, to advertising and commerce, to campaign orchestration. They covered the spectrum of Adobe’s industry groups — retail, travel and hospitality, media and entertainment, education, financial services and other key strategic verticals.

Adobe’s values are to be genuine, exceptional, innovative and involved. Those four principles guide the behaviors and expectations of everyone working at the company. As such, Adobe’s team members, in all areas of business, live and breathe those values every day.

Looking at a company’s acquisition history is a valuable piece of information for any salesperson because it helps you to understand what their future bets are and in which direction the business is going.

Sales approaches and tools

At least until 2008 and maybe a bit beyond, sales organizations were hard-pressed to integrate data from spreadsheets into Customer Relationship Management (CRM) tools.

It accentuated my belief in caring as an irreplaceable intangible in the salesperson’s make-up and mindset. Obviously, if you don’t have the right technology or price point, you’ll be facing an uphill battle to close any deal. But if those things are equal, caring can be the key differentiating factor, and you can do that with no experience at all.

The Digital Age has given today’s clients a nearly infinite level of information at their fingertips and created buyers who are much more sophisticated than ever before.

Reviewing static product documents and specifications is not as memorable or useful without seeing how products come to life for your customers.

Caring is not a sales methodology. Therefore, it should not be thought of as a selling style on which to base your actions.

I needed a system to build pipeline, categorize deals and qualify leads. More importantly, I needed a system with which I could develop automatic persistence. Perhaps the most magical thing about sales — in my opinion — is that the amount of time invested has nothing to do with the outcome. The ideal pipeline should extend through several quarters and include the right mix of small and large deals. Smaller deals are the ones you should be able to close with a standard go-to market strategy.

After you’ve zeroed in on an individual client, you should visualize what the endgame looks like. You need to know the various terms of a typical contract at your company, so you can start to plan for what an ideal match between your offer and your client will look like at the end of a sales cycle.

The last thing any salesperson wants to do is waste time chasing deals that aren’t doable. The most artful way to establish your system is to find the right balance between pipeline build and execution.

Sales frameworks

The Flywheel is an overarching framework for Amazon’s business that makes management and strategic decisions much more consistent. Providing an excellent customer experience is where the Flywheel — or as some at Amazon call it, the Virtuous Cycle — begins, ends and continues (hence, the analogy to a cycle or wheel). By customers consistently engaging in positive interactions with Amazon, the company organically generates growth, which leads to lower costs and lower prices, which only enhances the customer experience, and on goes the cycle again and again.

Strategy consultants at McKinsey use a different one called the Minto Pyramid Principle (MPP), which was detailed in a book by Barbara Minto in 1978. MPP is orchestrated just the way it sounds. Start with a main idea or the solution to a problem. Group supporting arguments in three buckets beneath that initial solution. And finally, list additional supporting ideas beneath each of those.

Frameworks and systematic approaches can seem unnatural and appear difficult to apply at first. You need to resist any urge to ignore them, however, because they can increase your problem-solving ability by epic proportions.

At its core, ValueSelling® is a mathematical formula that focuses on minimizing risk to get deals done.

The formula states that the Qualified Prospect® equals the Vision Match Differentiated times Value times Power times Plan.

If you don’t have a clear Business Issue, it will be nearly impossible to maximize value for your client and gain the support of senior management. Other initiatives that are connected to the core business issue will end up coming before your solution.

To apply project management to your sales cycle, I suggest you first determine how many different activity streams, such as sourcing, legal, procurement, etc., you can operate at the same time. The more of these items you’re able to parallel process without overwhelming your to-do list, the faster you’ll accelerate the sales cycle.

The last framework that’s worthy to mention is the Time Horizon, which is a mental model I use to make sure my client conversations aren’t too focused on the short-term.

Dark side of sales

Occasionally, if you have an unusually good year, the company may choose to put a cap on your earnings. To make this challenge more difficult to deal with, a cap could be accompanied by an increased quota, a decreased territory or both. If that happens, there’s only one word I can say, which is … Congratulations! A cap means you had a year of stellar performance and that’s never a bad thing.

If you find yourself committing errors you don’t ordinarily make, take it as a signal to buckle down, prioritize, and get back to your routine.

Acquisitions and reorganizations are a “certain uncertainty” in the business world. They’re certain to happen, but it’s uncertain when and how it will all settle. Acquisitions and reorganizations are going to happen many times throughout your career, and there’s nothing you can do about it. There’s no point in wasting too much of your time worrying and speculating about it. Over time, you’ll notice that those who expend their energies in that way either don’t stick around or are asked to leave. If you value the vision of your company, focus on helping the team to deliver it. Pour your energy into becoming an example of what your company aspires to be.

You could also find yourself in a situation where internal teams have conflicting financial incentives. A little internal competition is healthy and fun but not to the point where the team suffers.

Tough conversations

It may seem uncomfortable — even unnatural — to steer toward tough conversations, but when circumstances call for it, you’re far better off initiating them than avoiding them.

Once you’re thoroughly prepared, I suggest following a simple, three-step process for engaging in tough conversations. This process enables you to express empathy because you’ll be identifying with the situation and confirming it with the other party. By following this process, you’ll demonstrate a willingness to partner on a mutually agreeable solution, rather than acting as an adversary getting ready for confrontation:

  • Confirm the situation
  • Explore options
  • Define actions

Sometimes, an entire client relationship hangs in the balance of one conversation.

Ensure you have the necessary internal executive buy-in to support the alternative solutions you design. Senior management may have the ability to create special terms for pricing, services or other parameters that you don’t have the authority to approve.

If the only thing a client does during your meeting is politely nod their head up and down while saying, “Yes”, you should rethink your approach. Don’t mistake a lack of pushback in your initial client interactions for an earnest desire to move forward.

If you’re not telling them anything new, they will not see a need to change their current situation. Inaction will seem to be the best option to them.

There are many ways to educate your clients. One way is to tell them an insightful story around a new economic reality that’s been created from the evolving technological landscape.

A lot of clients work through a bewildering array of inefficient services and ineffective technologies weighing down their operations. In severe cases, ongoing operations can become unmanageably expensive to maintain due to an abundance of external service providers that end up preventing the company’s employees from taking ownership of their systems, data flows and ability to directly execute on their overarching business goals.


Mastering risk is essential to taking your sales career to the next level, which is why I recommend tackling it head on rather than taking a passive approach, as if it might go away by ignoring it.

Value selling, project management, initiating tough conversations, learning from horrible meetings — they’re all general sales practices to attack risk, directly or indirectly.

Happy ears is a condition that allows risk to creep into a deal and can cause salespeople to think their deals are larger and more of a sure thing than they actually are.

If you’re attacking risk correctly, you may get accused of being somewhat paranoid. That’s okay, because what some people interpret as a form of neurosis, more experienced sales leaders will see as due diligence.

Attacking risk is critical to managing the sales cycle effectively.


Many paths to success exist in the game of sales.

The first person that comes to mind when I think of sales role models is Steve Fay. He has such deep knowledge of Adobe’s products that he could easily transition to any role on any deal team. Michael Lacy always pinpoints exactly what the ideal path needs to be to get the deal done as quickly as possible, and in the way that provides the best results for all parties. Bill Sellers is another prime example of what a great team leader looks like. He places an emphasis on trusting the team to get the job done. His forte is in finding the various strengths within his team, putting faith in them and ensuring they have all the same deep client knowledge that he has.

The importance of team leadership becomes especially clear when you realize how it forms and shapes your immediate team. You can control some things in the sales cycle, but others you have no power to manage. Team assembly is likely one aspect you do not have complete control over. It’s still your responsibility, however, to bring everyone on the team up to speed.

Having a specialist or solution consultant on the team who can go deep on the technology you are selling is key.

Subject matter experts also offer a unique perspective to evaluating risk and sources of potential value, because they might be able to advise on nuanced ways to leverage the technology and / or integrate applications of which you may not have otherwise been aware.

Successful teams usually develop multiple client stakeholders in pursuit of a deal, rather than relying on a single-threaded approach where the team is funneled through one point of contact with the client.

Some people keep too much information to themselves, rather than sharing knowledge that could improve the team’s chances to excel.

Poor internal selling usually results in a deal not getting the support it needs regarding resources, contract support, legal support or validation of the deal structure.


The following is a generic list of value:

  • Additional Revenue
  • Cost Savings
  • Time Savings
  • Risk Reduction
  • Regulatory Change
  • Corporate Transactions
  • Partnerships
  • Personal Interest
  • Training
  • Access
  • Resource Alignment

Capturing hidden value involves not only a prioritized list of potential sources, but also requires the mentality to analyze, brainstorm and discuss various ways to track down value for all your clients.

When explaining value to the client, use their language and metrics.

I like to call this growing the pie because bigger deals come from not taking a bigger piece of the same-sized pie, but by making a bigger pie for everyone involved.

Going outside your role and product are two key actions that will grow the pie and expand your prioritized list of hidden value.

Shun the idea of staying in your lane. Instead, look holistically at the organization for which you’re working. That wide-angle lens could provide an opportunity for you to make a big difference internally, which can only improve your ability to close bigger and better deals more often.

Large deals

Identifying an exceptionally large deal is similar to capturing hidden value because the mega deal is invisible at the beginning of the process. You need to be looking for the opportunity to create one.

A solid offer includes most of the following items: Contract, Technology, People, Plan, Value you’ve defined, The unique vision that only you, your company and partners can deliver.

You want to start your thinking not at the transactional level, but at the transformational level. Think big at the start.

  • Transformational deals require a tremendous effort, teamwork and can account for millions of dollars.
  • The next tier from the top are still large deals that require considerable focus, but they’re not quite as complex or time consuming.
  • Level three deals are less creative and mostly standard, go-to-market opportunities.
  • Transactional deals are usually in the tens of thousands of dollars or low six figures.

Sales success can be achieved with many different approaches by many different personality types.

You may also like
Thomas H. Davenport, Jeanne G. Harris: Competing on Analytics; The New Science of Winning
James W. Cortada: The Rise and Fall and Reinvention of a Global Icon
Introducing AI through ladder approach (Rob Thomas – IBM, published by O’Reilly media)
James Vlahos: Talk to me; Amazon, Goodle, Apple and the Race for Voice-Controled AI

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