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Winning with Win-Loss


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Winning Your (Un)Fair Share of Deals | Win-Loss AI Prompts | Fertile Ground

“Find the inherent weakness in your competitor’s strength.”

Spend too much time harping on weaknesses and you’ll quickly find yourself up Poop’s Creek without a paddle. 

That’s because most weaknesses are fixable.

But if a company has decided to really lean into one of their strengths, they’re not like to change course anytime soon. 

So look for the Achilles Heel in your competitor’s strength, exploit it, and you’ll be on your way to knocking them out of the deal. 

As much as I’d like to claim this competitive selling wisdom for myself, its rightful owner is the former Head of Sales at Gong Chris Orlob.

You’ll hear more from him in this piping-hot edition of ☕️ Coffee & Compete 🤜🤛

Let’s roll,


🎥 How to Win Your (Un)Fair Share of Deals 🎥

chris orlob is a sales coach and former head of sales at Gong.

Sharing is caring in every aspect of life except for competitive deals. It’s okay to get greedy with your fiercest competition in neck-and-neck deals

Beyond general sales execution, preparation and enablement, sellers need to focus on how they can “rig” the deal in their favour.

And according to this week’s guest on the Competitive Enablement Show, former Head of Sales at Gong Chris Orlob, there are three crucial parts of the sales cycle you need to influence. 

1️⃣ The buying criteria 1️⃣

Every problem has a root cause. Every buyer is trying to solve a problem.

If you can shape their perception of what the root cause is, and then position your solution as the only one that can address that root cause, you’ve rigged the buying criteria in your favour. 

“Can you get the customer to answer in such a way that they agree that the root cause of the problem that only you can solve?”

Draw a clear line between the problem and your solution, and be prepared to champion that POV across the entire buying committee. 

2️⃣ The buying process 2️⃣

Rigging the buying process boils down to adding or removing steps in the deal cycle depending on who the competitor is. The goal here is to draw extra attention to their weaknesses — in addition to your strengths. 

For instance Gong’s chief rival, Chorus, was a cheaper option. This is what Chris would have done if, in an alternate universe, he were selling against Gong. 

“I would proactively recommend they get procurement involved in the buying process. If procurement grinding everybody down on price, I’m the cheaper one, so I’m going to win that argument.”

Once you dive deep into the competition’s strengths and weaknesses, you can begin to architect the sales process to your advantage — and to their detriment. 

3️⃣ The buying committee 3️⃣

It’s not enough to only work with your main champion. Today’s sellers need to be multithreaded with multiple stakeholders to influence their decision-making. 

Use the rigging you’ve done in the buying criteria to inform your communication with every stakeholder within the organization.

And as you add or remove steps in the buying process, consider which members of the buying committee are key to your success. 

Watch and listen to the full episode now to dig deeper into these three takeaways, and more real-life stories from Chris’s experience.

🔥 Three AI Prompts to Build a Win-Loss Program Plan 🔥


All AI all the time. It’s here. We’re using it. Let’s learn how to use it together.

Registration is officially open for the Compete Network’s Winner’s Circle event — and we’re talking all things AI. 

One of the speakers, VP of Win-Loss at Klue and founder of DoubleCheck Research Ryan Sorley, has already dived into the AI of it all when it comes to win-loss. 

Here are three prompts you can use to leverage your favourite GenAI chatbot to help build a win-loss program plan. 

  • I’m a product marketer working for a B2B technology company. I’ve been asked to build a super powerful win-loss analysis program to help support our sales, marketing, product and leadership teams. Our goal is to improve win rates. What steps should I take?
  • Please provide the benefits of a win-loss program to the following teams: Product Management, Sales Leadership, Sales Enablement, Customer Success, Product Marketing, Executive Leaders, Board. Please create sections for each role and list the benefits in bullet format. 
  • Now please outline a set of open-ended win-loss questions that align with the aforementioned benefits. Please provide no more than 20 questions. The order of the questions should align with a buyer’s evaluation process. Please feel free to create new sections. 

Next time you’re in a pinch coming up with a win-loss plan, lean on these three prompts to get you on your feet. 

And make sure to register today for the Winner Circle to get more great AI-inspired insight like these prompts!

👭Coffee & Compete Community Corner 👬

You wouldn’t think of Target as fertile ground for messaging inspiration.

But when you’re a Competitive Private Investigator and Content Wizard like Eric Holland, inspiration can come from strange places. 

A massive shoutout to Eric for making my job as the Coffee & Compete Community Corner curator very easy 👇


Thanks for reading this week’s edition of Coffee & Compete. As always, please reach out to me and the rest of the team with your thoughts and feedback. 

And If you know someone who isn’t already subscribed to Coffee & Compete, be a good friend and tell them about us.
win loss analysis template

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