Navigating the Internal Sale (Startup Founder Sales Series, Part 10)

Growing up, some of my favorite books were the Chose Your Own Adventure series. Every few pages of the book, you were posed with a question and a few responses. Based on your choice, you were sent to a page to continue with the adventure. The wrong choice however might send you towards an untimely misfortune or even death!

What I loved about the books was the puzzle. There was no obvious direction, you had to make your best guess on whether your decision was the right choice or not. This is probably what led me to pursue engineering in college and eventually a job as a software engineer.

Sales is also a puzzle. It’s a human puzzle working through emotions, biases, and motivations. In sales, you play the roles of psychologist, detective, and diplomat all at the same time in order to weave your way through the complicated web of influence, power, and process to hopefully win the deal.

So far in this series, I have walked you through the steps of building awareness to gaining interest from prospects. At this stage, the probability of winning the business goes up dramatically. Yet there are common mistakes I have seen over and over again that can lead to a good deal unraveling.

The potential for any of these mistakes to impact your sale depends on a few factors:

• Size of company
• Size of deal
• Size of risk
• Size of solution

If your prospect is a smaller business or startup, decisions tend to be made faster because there are less intermediaries and approvals required. You have more access and engagement with the decision makers than with larger enterprises, where decision makers are more removed from the teams evaluating solutions.

Deals of smaller monetary value usually do not require as many steps to complete. As the cost of the solution increases though, more approvals are required, sometimes even requiring multiple reviews in order to allocate limited budget that also must cover other projects and solutions.

With any new solution, there are certain risks that are entailed. Solutions that already familiar, are not part of mission critical operations, and handle less sensitive data are deemed lower risk and are easier to bring into an organization. Highly advanced, novel, or critical solutions however invite more scrutiny.

Closely related to risk is the overall complexity of the solution. Point solutions that can easily plug into existing workflows and systems are easier and faster to implement. Highly integrated and broader solutions however have many moving parts and dependencies, requiring more input and analysis from other teams.

The common thread in all of these factors is the time in which to get a deal completed. Time is the ultimate enemy of every sale because the longer it takes to sign the deal, the more variables that are introduced that can upend buying your solution. Deals are often lost because of a restructuring, a champion leaving, political maneuvering, or other unexpected and urgent needs.

To avoid time becoming your enemy, you need to effectively navigate the deal along every step. I have outlined eight considerations to avoid unpleasant surprises that sink your deal:

• Co-sell with your champion – This was covered in the last post, but the key point is to always have ongoing and regular communications with your champion. They are motivated for you to succeed, so make sure you are actively coordinating and collaborating with them.
• Sell high, wide, and deep – Having a strong champion is helpful, but having one strong supporter is risky if your champion leaves or has a change of heart. Build relationships high in the organization with executives, wide across to other relevant teams, and deep into layers of management and individual contributors. The more people that hear your story and know who you are, the more information you gather and the less likely you will be to be dismissed. Relationships matter.
• Tracking the deal – This is when having a CRM (customer relationship management) system is worth the price. When you make it a habit to update the CRM with your contacts, messages, meetings, and notes, you have a history of your sales. Review that information on a weekly basis and ask what is missing, what has changed, what is new, and who else do you need to speak with. Let data be your guide.
• Mapping influence – When you sell high, wide, and deep and you are religious about tracking your steps in the sale, you start to notice how people interact and operate in an organization. You not only see the organizational chart, but you also can also trace the lines of influence and power that affect budget and decision making. Map out these relationships and identify people that you need to build relationships with that can help you secure the deal.
• Learn their buying cycle – Every company has a different process for buying. You need to understand the procurement process, required risk, compliance & legal reviews, approval needed for budget, security, and architecture, and the general timeline for completing all steps before a deal is finalized.
• Questioning assumptions – A common bias in sales is to focus more on good news and to extrapolate incomplete information into a positive developments. Avoid this tendency and always ask yourself “what information do I not know”. Be willing to ask hard questions of your prospect and internal champion on timelines, introductions to decision makers, the buying process, and key blockers and obstacles in your deal. Never let “happy ears” distract you from being skeptical.
• Getting caught up on price – When price is an ongoing part of every discussion, it is a sign that the value of your solution is poorly understood. Avoid giving away your solution or caving to the call for discounts by moving the conversation back to the customer problem and the positive impact that solving the problem provides. When price comes up, ask your prospect to confirm what they see as the problem and the potential impact of solving that problem.
• Avoid going negative – It might feel good to bash the competition once in a while, but this could cost you internal support. As a startup, you are often trying to unseat an incumbent solution or existing process. Going negative causes those supporting the existing solution or process to be threatened by you, creating enemies. Focus on emphasizing the positives of your solution and the benefits from their perspective so that you win supporters.

When you are on top of building relationships, understanding the organization, and avoiding common traps, you are well positioned to win. However you still need to seal the deal. Before you get there, this often means a journey through a dizzying series of contract and legal reviews. In my next post, I will share some of the more common sticking points and areas of caution when it comes to legal side of closing deals.