Sales advice

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I’ve done over 2000 sales calls in the last 7 years, selling mostly high-ticket B2B deals. Here were the biggest lessons I took away when it comes to effectively selling over the phone and Zoom.



Hey SGH community, I wanted to share some of my major learnings from my career in sales.



Over the last 7 years, I’ve spent time on everything from making cold calls and prospecting as an inside BD rep, negotiating and closing large enterprise deals as an AE, and now hiring and training high-performing sales teams now as I run my company.



I thought I’d package up everything I learned about the sales process and running sales calls into this single article in case anyone here is trying to build their own playbook.



Before we begin, I want to give a shout out to Aaron Krall who runs this group. He has an accelerator which can definitely help you if you’re looking to scale, so hit him up if you need help. His content has been valuable to me over this last year since I joined SGH.



Note: I do want to preface that I’ve only ever been in B2B sales where the close involves a sales call and the service/product was higher than $5k customer LTV. With these solutions, conversations tend to be more consultative and higher touch. I think this approach works quite well if you’re running a pricier SaaS product, agency, or consultancy. Otherwise, this call-focused closing strategy might be a poorer fit.



Systematic Sales Talk Track



Sales calls should always carry a consistent cadence when done properly.



And one cadence has been especially effective for me in my last 7 years of selling, regardless of the industry I was in.



Here’s my breakdown.



Step #1: Discovery



Everyone knows to discover. It’s nothing revolutionary.



But it’s HOW you do it that dictates success.



Far too many reps and founders treat it like an afterthought, where you just ask a couple canned questions over 5 minutes and move on to the demo.



But the truth is, a poor discovery will ALWAYS lead to a janky demo.



Why?



Because without discovery helping you first understand what the prospect’s problems are and why they exist, you can’t show how you can fix those problems.



Imagine if you went into a doctor's office hoping they could help you fix a health problem.



Yet without even sitting you down, taking your temperature, or even asking a few simple questions, the doctor just gives you a prescription and tells you to get out.



How confident would you be in that prescription?



Great discovery isn’t just about asking the “what” of the prospects situation.



It’s about asking:

•	Why have you been doing it like that?

•	How has this doing it like this actually impacted your business?

•	How is this impacting you emotionally and mentally?

•	What would be the ideal version of the future instead?



Essentially, going deeper.



Learning the rationale behind previous decisions, the emotional impact of those choices, and the long term business ramifications of their actions.



Yes, discovery like this might take 15 to 25 minutes. But it’s well worth it.



Step #2: Tailored Education



The reason why we go so deep into discovery is because it then allows us to execute Step #2, which is to educate.



My favorite sales book EVER is called “The Challenger Sale”.



The premise is that when it comes to expensive software or service purchases, the buyer needs to feel safe and secure in the decision. These are not impulse buys like an Amazon black friday sale.



To build that safety and security, it’s important to take on the role of a “trusted advisor”, who can teach the prospect something they didn’t already know.



We want to challenge their existing belief systems, highlight things they are doing which are costing them, before showing them what is “the better way”.



And this earns us trust and credibility.



A good doctor will diagnose your problems, teach you what you’re doing wrong, and then give suggestions on behaviour change that’ll fix your issue.



By the time they’re done with this step, you should have so much faith in them that the prescription and choice of treatment is something you just accept.



(note: this is when you have a good doctor. I recognize sometimes, you’re unlucky and get a doctor that doesn’t inspire much faith haha)



So how do you do this in a B2B context?



As an expert in your field, teach your prospect something they didn’t know.



Audit their process. Actually break down the elements in their strategy/approach that could be better optimized or improved.



Give real world examples of similar people who made those same mistakes, and the consequences of those mistakes (ie. leaving money on the table, wasting time, getting poor results)



But then, share what they SHOULD be doing instead - teach them what process WOULD work, and the positive results they’ll see once they implement this change.



By doing this, you improve rapport, and credibility.



They’ll trust you more since they feel like your intention is to help. Afterall, MOST founders and sales people immediately start pushing product aggressively… It’s a big turnoff.



But when you take this approach? You’re actually building a relationship and helping.



Pretty different vibe. It leads to a much more open prospect.



Another cool thing is a concept called “rational drowning”.



This is when you overwhelm the prospect so much with your "constructive criticism", that they come to the conclusion they have to change.



But even so, they ​​feel like they can’t handle it all by themself.



Maybe it’s because it’ll take too long, cost too much money, or is simply outside their expertise to course-correct their mistakes.



But regardless, after hearing all your recommendations and insights, they’ll feel more helpless and even feel a sense of desperation.



“Rational drowning” primes your prospect to be in an emotional state which is far more receptive to hearing about your product/offering.



Now, with that being said, nothing I’ve said is about your product yet. In fact, so far in the convo, you really don’t talk about the product at all.



Up till now, the conversation has been more about learning about them and teaching them.



Something to highlight during this stage though, is when you’re putting on your “Challenger” hat, DO NOT make it seem like the mistakes are THEIR FAULT.



You need to paint their mistakes as being normal, and stuff everyone struggles with.



Telling someone they are an idiot for making so many blunders will only hurt you. Prospects take it personally.



But when you remove the blame off their shoulders, it’ll feel more like you’re on the prospects team. Together, you’re trying to attack the problem.



An easy to understand example would be if you’re a personal trainer who meets an overweight person.



If you want to inspire them to change, you don’t want to just list off every mistake they are making and tell them it’s their fault for being overweight.



Even if your point is valid, they won’t like you anymore and it’ll be impossible to proceed.



Instead, talk about their bad habits in a non-accusatory way.



Empathize with them about how their habits came from growing up in a family that didn’t prioritize health.



And now that they work full-time and have kids, it’s really hard for them to make health a priority.



It’s not their fault. This would have been the likely outcome for most people.



But now they have the chance to change.



However, if they don’t decide to adjust their behaviour now, it DOES become their fault.



Empathy plus the “Challenger” mindset is how people are inspired to change.



Step #3: Customized Demo



So we finally get to the “prescription” part of this analogy - the Customized Demo.



By now, the prospect knows exactly what they’re doing wrong, and the consequences of their actions.



They feel helpless about their situation, and are practically begging you to show them your offer by this point.



Now is when you demo.



Your offering is the “prescription” that will come save the day and fix all their problems.



With that being said, the “demo” portion isn’t just a simple run-through of your features and process.



Too many founders and sales people get here and ruin the convo by giving a janky, irrelevant demo.



But that’s not going to be you, if you read on!



The most important key to giving an epic sales demo is that you are highlighting CHANGE instead of highlighting features.



Because in reality, people don’t care about features.



They care about themselves and their crappy situation.



So what do you demo?



You demo the exact method that enables you to GET RID of their bad situation and improve.



This is where your features come in.



Your features are the vehicle to attaining that transformation.



This is a mindset shift, and a total reframe in how we run sales calls.



Now, to do this properly, we rely on having you do GREAT discovery.



Because the prospect has a unique set of problems that is different from anyone else.



So the only way you can demo THEIR IDEAL TRANSFORMATION is if you first know what type of transformation they even want in the first place.



That’s why we ask all those questions in the beginning to learn about their dreams, fears, obstacles.



This then enables us to understand which features are even relevant, and on the flipside, which are irrelevant.



Because you want to share only the relevant features.



The irrelevant features? You want to skip them.



Afterall, they don’t directly contribute to helping them attain their transformation.



Now, for all my product-focused friends here that are freaking out because you poured your heart and soul into making your offering and every feature the best ever…



Remember, it’s not about you, it’s about them.



The prospect’s desire is not to see a cool product demo or hear about your awesome service.



They just want to hear enough to know it’ll make an impact in their situation.



The more you talk about stuff that is outside of their priorities, the more they’ll tune out.



Your ego is secondary in this situation.



Demo how you can help them achieve their specific vision of change using your features and process, and they’ll want to work with you.



Step #4: Close



Just because the demo is done, doesn’t mean the call is over.



In fact, even if the prospect loves your offer, it might still not be over.



What’s supercritical in closing deals is making sure EVERYONE on the prospect’s team who has decision making authority is bought in.



Because all it takes is one unhappy camper on the buying side to kill a deal.



With large deals, there’s often 3 or more people who has a say.



So for you as a sales person, it’s important you ask your main contact, “who else needs to be involved?”



When you map out the stakeholders, you can then set in motion a plan to bring everyone else into the conversation so you can also win them over too.



Remember though, pitching a VP of Marketing is different than pitching a marketing manager. They have different motivations and concerns, so you have to modify your talk track in accordance.



Once you have everyone on their team bought in, it’s all about negotiating the best price, creating urgency so you can close quickly, and overcoming final objections.



Those three things by themselves could warrant a full article, so I’ll just leave it there so you recognize they exist and are important.



Final Notes



This process is what I consider “textbook”.



In an ideal world, you have a very clean disco call -> sales pitch -> close.



But in reality, sales is a roller coaster.



It can take detours when you least expect it. Very rarely does it always go in a straight line.



Case in point, the most annoying deal I ever closed was when I was selling enterprise martech SaaS.



I had an opportunity with Yellow Pages (yup, they still exist) that was worth around $35k.



It seemed like it would be an easy 1 demo close, given how happy my point of contact was.



Then he got fired, their stock price got cut in half, the CEO got replaced, and the marketing team lost 80% of their budget.



What I initially thought would take 3 weeks turned into a full year and a lot of creative problem solving to turn things back around.



This is a great roadmap, but you still have to be flexible.



Anyhow, hope this helped. If anyone has thoughts, leave it in the comments below.



Once again, hit up Aaron if you’re trying to scale your SaaS, he’s a good resource.