4 factors that contributed to winning large & complex sales deals

4 factors that contributed to winning large & complex sales deals

Stepping into an account management or sales leadership role can be challenging, especially if your sales deals can take 12–24 months or longer to secure. Complexities show up throughout the purchasing cycle, from qualifying a new opportunity, engaging clients with presentations and sharing your solution’s capabilities to producing, presenting and negotiating a project contract to implement the solution. As a sales leader, how can you remain effective throughout such a lengthy process, especially when working on large, complex deals? How can you focus on your customer’s challenges and avoid becoming sidetracked? In this article, Markus O. Winzer, a former sales leader and current leadership, effectiveness and results coach, outlines the four factors that contributed to winning large, complex and difficult deals for him.


Feb 05, 2023

7 mins read

When you work in sales and a client is seeking a way to address their complex problem, the right solution often involves multiple components and may include people, process and technological elements. Examples range from implementing new CRM and software systems to systems transformation deals like migrating billing or operational systems. These types of sales deals can take 12–24 months or longer to secure and involve multiple complexities throughout the purchasing cycle. As a sales leader, how can you remain effective throughout such a lengthy process? In this article, I reveal the four key aspects that were instrumental to me winning some large, complex and difficult deals when I worked in sales, which you can leverage in your role. 

McKinsey & Company suggests “Understanding customer needs and product knowledge” as the most important quality during the purchasing process. This translates to understanding your client deeply and from all angles, including understanding the perspective of their clients, management team, board members, operations and teams. It also means appreciating the consequences, impact or cost to them of not addressing their need combined with your knowledge about every aspect of your company’s ideal solution. 

Challenges that can occur in the pursuit of winning large, complex sales deals

In pursuit of providing the most effective solution for the problems your clients face, many challenges and distractions can crop up, including (but not limited to):

  • Focusing on the things you don't have visibility into,
  • Realising your company’s solution is inferior to your competitor’s solution,
  • Becoming aware that your client is listening to a competitor who is prepared to offer a solution for a lower price,
  • Not knowing the list of priorities for the client at all levels: working level, management level, C-Level and board level,
  • Limited visibility of budgets, priorities and time requirements.

While there are many readily available solutions in the market to support new sales professionals, most focus on surface-level behaviours such as structuring winning customer presentations or tender response documents and improving persuasive skills. However, I would like to draw your attention to four key factors that go deeper and get to the root cause of the matter, beyond behaviour, based on my personal experience as a sales leader.

The challenge

In my journey as a sales leader, I – like most sales professionals – faced many challenging situations, especially when pursuing large and complex sales deals. I recall when our main competitor offered a client I had been working with for some time to deliver a project for a significantly lower price. I was faced with the decision to either lose the account or come up with a more valuable approach and response to our competitor’s offer. So what did I do? 

An ontological approach to winning large, complex & difficult sales deals

Looking at the challenge from an ontological perspective, I drew inspiration from what Ashkan Tashvir writes in his book, Human Being: “The ultimate goal is to work in real time and have the ability to predict a potential future scenario and be ready to act or respond appropriately”. So how does that apply to the sales conversation? The answer is that it takes a high level of awareness together with three other factors to respond appropriately.

Factor 1 – Awareness 

Ashkan describes awareness as “the state of being intentionally conscious of your consciousness. It is how you relate to what you know and understand as well as what you don’t know and don’t understand”. How does this relate to pursuing a large, complex sales opportunity? The answer is that it is critical to bring your awareness to everything you know and understand about the client and everything you don’t yet know and understand. For example, what is their need? Who in the organisation has the need? What is the cost to the organisation of not having the right solution? Who else could they rely on to provide a solution? With whom do the decision-makers have a relationship? In our case, through a conversation with my client, I became aware that our competitor had offered them a different and cheaper option. I was subsequently told our offer was no longer the best. 

Factor 2 – Care 

It takes a high level of care to understand and bring your attention to what your client needs. Care impacts how you relate to what matters to you (and others) and influences you in such a way that you ensure the matters and people you care about are supported, protected or dealt with in the best manner possible. Care leads you to address whatever is necessary to nurture the person or matter and dedicate the appropriate level of time, resources and attention to them.

As a sales leader, care is an essential quality throughout the buying process. For starters, caring about meeting your monthly or quarterly targets moves you towards action. Excellent sales leaders also care about making a difference for their clients. They are passionate about serving, and understanding and solving their clients’ problems. The best sales leaders also empower individuals throughout the buying journey in making decisions. 

In my case, I did not want to give up so easily. I cared deeply about my client and their challenge of meeting aggressive deadlines for providing their internal clients with the right technical capabilities. And I knew their clients preferred a low-risk approach and did not want to prioritise price over a lower-risk technological solution.

Factor 3 – Resourcefulness

Resourcefulness enables you to go beyond existing norms. It is living life from the viewpoint of abundance and being effective at finding or creating new ways of doing things and solving problems. When you are being resourceful, you will often look beyond pre-existing knowledge, tools, conventional systems and traditional methods to find solutions. When sales professionals and account managers are resourceful, they can look beyond the current state of the client’s organisation. They understand deeply what the individuals and the organisation want as a whole.

Imagine the following scenario. You are in contact with the leaders of an organisation’s technology, project management and operational departments. Each leader has different personal and organisational goals. As a resourceful sales leader, you can sometimes understand an organisation better than it can understand itself. When you have the end-to-end picture of where the organisation wants to go, you can provide a solution that meets both individual and organisational goals. 

In my case, I understood that my client’s organisation had various functions. For example, the operational unit’s internal goal was to release two functionalities in sequence, beginning with phase 1 technology enablement followed by phase 2 technology enablement. However, I knew a rollout like this would result in a six-month delay before they could reduce operational costs with the phase 2 technology enablement. I also knew we could not compete on price, meaning we needed to find more value. The big breakthrough came late one night when our technical teams found the answer we had been seeking: provide both technologies (phase 1+phase 2) simultaneously with a reduced scope. It was a technically more complex solution, which provided greater value earlier and enabled the operations unit to save costs six months sooner.

Factor 4: Partnership 

Partnership is living from the viewpoint of being in union with others, an entity, team or organisation in the pursuit and fulfilment of a common purpose. It is when you are available to join with others who may share the same values, goals or commitments to create a disproportionate outcome in comparison to what each of you could possibly achieve alone. 

While the traditional approach is to inauthentically ‘partner’ with a client while pursuing a sales deal, a more effective alternative is to build an authentic partnership with them so that 1+1=3. Let me explain what I mean by referring back to our example. By partnering with our client, we were able to provide a world-first complex technological solution and deliver it on time. This would not have been possible had we not decided to intentionally and authentically be in partnership with them. Partnership, as a Way of Being, not only transformed our relationship with the client but also with multiple delivery partners at the time. This became the basis for a multi-year partnership between our companies and teams, resulting in more follow-up projects and the delivery of several other world-first technical integrations.


If you are a sales leader who often faces challenging situations due to the complexity and size of the sales deals you are working on, I encourage you to focus on four key factors that get to the root cause of a matter beyond surface-level behaviours and techniques.

  • Awareness
  • Care
  • Resourcefulness
  • Partnership

When you combine your approach to continuously raise your awareness to respond to growing and changing environments for your clients, competitors and partners with your care to put your clients and their needs first, you can focus on what really matters. Being resourceful means going beyond existing norms to find a solution that may not have been tested and trialled before. And when partnership is central to developing solutions, especially between partners, clients and pre-sales teams, anything is possible.

As Margaret Heffernan puts it, “You cannot fix a problem that you refuse to acknowledge”. If you are curious to discover how to shift your effectiveness as a sales leader, especially when striving to win large, complex and difficult sales deals, I invite you to contact me to discover what’s possible.


Engenesis Platform - Personal growth, self development and human transformation.





Being Profile® Self-Discovery CourseVenture Foundations CourseBeing Framework™ Leadership FoundationsBrowse Events

Need Support?

+612 9188 0844

Follow Us

Copyright © Engenesis Platform 2024