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<\/a><\/p>\nWith enterprise-level selling, deals take time, patience, and a knack for navigating the labyrinth of stakeholders, pain points, and tailor-made solutions. That\u2019s why these deals, with their extended cycles and multifaceted conversations, earn the title of complex sales. After all, you call \u2018em how you see \u2018em, right?<\/p>\n
In this post, I\u2019ll dive into what makes complex selling so, well, complex \u2014 and how you can truly conquer the craft of closing these big-ticket deals without breaking a sweat. Let\u2019s unpack it together.<\/p>\n
Table of Contents:<\/strong><\/p>\n <\/a> <\/p>\n Overall, a complex sale is marked by three key elements:<\/p>\n Complex selling is so unique \u2014 and challenging \u2014 that it\u2019s less about \u201cpitching\u201d your product\/service. Instead, complex selling is all about positioning yourself as a credible advisor.<\/p>\n If you\u2019re dealing with a complex sale, be prepared to do a little more work and \u2014 depending on how you feel about going the extra mile \u2014 for your role to extend far beyond the title of \u201csales rep.\u201d Annnnd if that sentence just made you immediately stop reading \u2014 which I totally understand \u2014 check out a few statistics from this article I recently wrote<\/a> (ft. data from HubSpot\u2019s 2024 State of Sales Report<\/a>):<\/p>\n Clearly, the insights don\u2019t lie. Just as I mentioned above, complex selling isn\u2019t surface-level. It\u2019s all about building trust, navigating relationships, and, most importantly, delivering real value to your customers.<\/p>\n If you\u2019re still looking for clarity on what\u2019s involved in complex selling, have no fear. In the next section, I\u2019ll break down its foundational components, hopefully giving you a clearer understanding of the intricacies behind these high-stakes deals.<\/p>\n <\/a> <\/p>\n Unlike transactional sales, closing a complex deal means convincing multiple stakeholders. The number of stakeholders and their positions in the company can vary depending on the industry.<\/p>\n For example, suppose you\u2019re selling technical software to a business. The final decision-maker may be the company\u2019s Chief Engineering Officer, but that could quickly change to the People Operations Executive if you\u2019re selling a productivity service.<\/p>\n However, in this example, the chief executive is the last person you\u2019ll have to convince, and a series of people below the C-suite will likely be involved in the process. Gone are the days of persuading one person to buy your product. With complex selling, it might be five, potentially 10. It\u2019s also possible that you may never meet all the people involved in the buying process.<\/p>\n Another great thing about complex selling? It\u2019s full of surprises.<\/p>\n If you\u2019re handling a complex sale, be prepared for some commitment; if you\u2019re wondering why this is, here\u2019s your answer: A complex sales process is way longer than a transactional sale; it may last anywhere from six to 24 months.<\/p>\n Without going into too much detail, a longer sales cycle allows all engaged parties to take the time to understand the product and its benefits. While a longer sales cycle may sound daunting, when you\u2019re working with B2B deals, you learn to be grateful for the extra time.<\/p>\n Trust is the only currency in a complex sale that\u2019ll keep the deal moving forward.<\/p>\n Complex sales aren\u2019t won with flashy presentations or buzzwords. They\u2019re built on good ol\u2019 trust and reliability. This means proving to your prospects that you\u2019re not just trying to sell them something. Instead, you\u2019ve got to show them that you\u2019re genuinely invested in solving their problems. This may mean more rapport building on the front end, but when it comes time to close the deal, you\u2019ll be happy you did the brunt of the work in the first place.<\/p>\n If you have a textbook with cookie-cutter methodologies on how to approach a complex sale, throw it away. Right now. Complex selling calls for personalization at every part of the process, including the proposal stage, which means you\u2019ve got to put some elbow grease into ideating solutions for your clients. You\u2019ll need to dig deep into your discovery phase findings and tailor your pitch to speak directly to their pain points.<\/p>\n This isn\u2019t just about tweaking a PowerPoint; it\u2019s about showing them you \u201cget it\u201d and offering a solution that aligns perfectly with their unique needs. In short, customization isn\u2019t just a nice touch \u2014 it\u2019s the difference between a \u201cmaybe\u201d and a signed contract.<\/p>\n <\/a> <\/p>\n While complex sales typically fall under the B2B umbrella, no two deals look alike. The diversity of industries and challenges within the B2B space means every deal has its own set of puzzles to solve, players to please, and priorities to juggle.<\/p>\n For example, let\u2019s talk commercial insurance sales. They fall under the category of a complex sale because they require insurance salesfolks to really know their client inside and out, including key areas such as:<\/p>\n Additionally, as their client\u2019s business grows or pivots, its insurance needs may change, introducing another layer of nuance. As a result, insurance sales pros must be proactive and ready to share individualized policies that align with their client\u2019s current and future needs.<\/p>\n And in addition to all these factors, commercial insurance sales often involve negotiations with various collaborators, from HR teams to CFOs, which makes the sales cycle extra lengthy.<\/p>\n This intricate balancing act, full of moving parts, is what defines a complex sale. In the end, success in commercial insurance \u2014 or any complex sale \u2014 requires a mix of deep expertise, adaptability, and the ability to navigate relationships with finesse.<\/p>\n <\/a> <\/p>\n Despite their differences, the complex sales cycle mirrors typical sales cycle stages. The cycle includes four stages:<\/p>\n During this phase, you\u2019ll likely spend your time familiarizing yourself with the business you\u2019re selling to.<\/p>\n At this point in the complex selling process, consulting with the business you\u2019re working with will provide you with a baseline understanding of their pain points and expectations (so you can get a clear picture of how your tool can address those problems).<\/p>\n You should know something else about this stage: It\u2019s quite a research project. You\u2019ll use this stage to find out everything you can about the stakeholders and their relationships to the service you\u2019re selling. Expect this stage to be where you\u2019ll figure out stuff like:<\/p>\n Gathering as much detailed information as possible from your client during this stage will make it easier for you to be successful as you move through the complex sales process and, eventually, close the deal.<\/p>\n During this stage of complex selling, you\u2019ll use the information gathered during the discovery stage to diagnose your prospect\u2019s issues. Understanding your client\u2019s pain points and how your product can solve them will pay off significantly and clarify why your solution is the best option.<\/p>\n If you convince your prospect that not<\/em> addressing the diagnosis will negatively affect their future growth, they\u2019ll be more likely (and, hopefully, eager) to engage with your solutions. Remember: At this point in the game, it\u2019s all about presentation, my dear reader.<\/p>\n If you\u2019ve reached this point of a complex sale, anticipate using your diagnosis to present stakeholders with detailed examples of how your solution directly addresses and solves their pain points. To do this well, you may want to include things like:<\/p>\n At this point in the complex selling process, you want to a) <\/strong>be ultra-confident in your solutions and b) <\/strong>ensure that any involved stakeholders are assured of your understanding of their situation.<\/p>\n Since these deals include multiple layered solutions, providing them with a detailed plan accompanied by tons of other materials will give them a well-rounded view of your offer.<\/p>\n After you\u2019ve done the work to convince all stakeholders of the benefits of your service, you\u2019ll do what you\u2019ve been waiting for: Closing the deal.<\/p>\n The final contract, which addresses significantly more solutions, differentiates a complex sales closing stage from transactional sales. A regular contract may outline one or two solutions, but your complex deal may address ten.<\/p>\n Maintaining contact with the client and presenting yourself as a resource after the deal is finalized shows them you\u2019re eager to help them should any issues arise. If this deal is part of a contract, maintaining a relationship can ensure the contract is renewed.<\/p>\n <\/a> <\/p>\n While the sales cycle for complex selling may be pretty straightforward, there\u2019s still much to uncover about what it takes to excel at it. I recently sat down with Trav Simat,<\/a> a leading Enterprise Business Development Representative (BDR) at HubSpot, to discuss:<\/p>\n Here\u2019s what he had to share regarding how to improve your complex selling skills<\/a> (and ditch any outdated sales tactics<\/a> that simply aren\u2019t working anymore):<\/p>\n When I asked Trav about any specific strategies he swore by when navigating a tricky enterprise-level deal, he told me something I wasn\u2019t quite expecting to hear. I think you\u2019ll be surprised, too.<\/p>\n \u201cWith complex sales, you have to be a product expert in order to provide the correct guidance,\u201d Trav told me. He then continued, \u201cThere\u2019s no doubt about it. You\u2019ve also got to have a deep understanding of what the customer\u2019s current challenges are, could be, and how your tailored solution is going to be able to drive results or make their business more efficient.\u201d<\/p>\n Evidently, Trav\u2019s advice is a reminder that in complex selling, knowledge is your greatest asset. Whether it be about the product you\u2019re selling, the person you\u2019re talking to, or the business you\u2019re working with, the more you know, the more likely you are to go farther in your deal.<\/p>\n When it comes to finding the right fit for a complex sales deal, Trav goes back to the basics: identifying his target market, also known as an ICP.<\/p>\n \u201cYou need to understand your ICP and what businesses can actually benefit from your solution before any discovery even takes place,\u201d Trav admitted. \u201cFrom there, you have to slowly build relationships and try and go as wide as you can to have as many meaningful conversations with as many prospects as possible that have decision-making power at the company you\u2019re trying to work with.\u201d<\/p>\n Like Trav emphasized, complex sales aren\u2019t just about finding any deal \u2014 they\u2019re about finding the right<\/em> deal. By honing in on your ideal customer profile and focusing on meaningful, relationship-driven conversations with key decision-makers, you\u2019re not just selling a solution \u2014 you\u2019re building partnerships that last.<\/p>\n Pro Tip: <\/strong>You can use HubSpot\u2019s Sales Plan Template<\/a> to outline your target market, amongst other things (like your prospecting strategy and overall sales goals), to make B2B selling effortless and stress-free.<\/p>\n When it comes to securing a complex sale success, Trav says that you\u2019ve got to occasionally abandon ship, especially when the prospect doesn\u2019t seem worth your time.<\/p>\n \u201cI\u2019ve also noticed over the years that the best salespeople can qualify and disqualify their products as quickly as possible in order not to waste anyone\u2019s time,\u201d Trav explained. \u201cA lot of people make forced deals that aren\u2019t there when they really should do a better job at disqualifying the deal and moving onto better opportunities that actually have a chance at closing. That\u2019s what truly separates the champions from the rest.\u201d<\/p>\n Knowing when to walk away is just as important as knowing when to push forward. The best salespeople don\u2019t chase every lead. Instead, they prioritize their time and energy on opportunities that have real potential.<\/p>\n <\/a> <\/p>\n Alright. We\u2019ve reached the end of the road. If you walk away from this post having learned anything from this post, I hope it\u2019s the following:<\/p>\n Complex sales aren\u2019t about landing the deal but delivering real, measurable value. When you approach each stage with care and intention, you set yourself up to close confidently.<\/p>\n So, take a deep breath, double-check your pitch, and dive in. You\u2019ve got this, my dear reader. After all, big deals don\u2019t just build themselves, and you\u2019re the person who knows exactly how to make them happen.<\/p>\n Editor’s note: This post was originally published in September 2020 and has been updated for comprehensiveness.<\/em><\/p>\n \u00a0<\/p>\n If you\u2019re like most sales folks, you already know that selling isn\u2019t one-size-fits-all. And, if you\u2019ve ever closed a deal, you know that your playbook changes depending on who\u2019s sitting on the other side of…<\/p>\n\n
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Key Elements of Complex Selling<\/h2>\n
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<\/p>\n1. Dealing with multiple stakeholders.<\/h3>\n
2. Managing a longer sales cycle.<\/h3>\n
3. Building trust and demonstrating value.<\/h3>\n
4. Customizing solutions to address pain points.<\/h3>\n
Complex Sales Example<\/h2>\n
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The Stages of a Complex Sales Cycle<\/h2>\n
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1. The Discovery Stage<\/h3>\n
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2. The Qualification and Diagnosis Stage<\/h3>\n
3. The Proposal Stage<\/h3>\n
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4. The Closing Stage<\/h3>\n
How to Win at Complex Selling<\/h2>\n
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1. Want to win a complex sale? Become a product expert first.<\/h3>\n
2. Understand your Ideal Customer Profile (ICP).<\/h3>\n
3. Like the Kenny Rogers song says: Know when to hold \u2018em, know when to fold \u2018em, and know when to walk away.<\/h3>\n
My Closing Thoughts on Closing Big Deals<\/h2>\n
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