Why most sales prospecting still sucks in 2023 and what you can do about it

If prospecting is your everyday grind, this blog post based on Collin Cadmus’ intriguing point of view in one of the recent episodes of The Modern SaaS Podcast might be worth your while.

Collin is a sales coach, advisor to multiple startups, and the host of the Collin Cadmus Podcast. When Aditya Kothadiya, Co-Founder and CEO at Avoma and the host of The Modern SaaS Podcast, asked Collin if he remembered any good prospecting examples that he remembered, he gave a surprising response:

Honestly, I'm having trouble remembering one but I think I know why. You don’t remember the good prospecting outreach that works because they don’t feel like a sales outreach. It’s because the sales rep takes their time instead of templating their outreach…

And that statement speaks volumes about what’s wrong with sales prospecting today in general. The Internet has made it incredibly easy for B2B salespeople to find and connect prospects, especially with social selling on LinkedIn. And yet, most sales reps ruin their chances of “scoring a date” with the right prospects because they rush through the process without putting a lot of thought into it.

If you want to listen to/watch the full interview, here you go:

In this post based on the podcast episode, we will cover:

• The reason most prospecting attempts fail
• The anatomy of good prospecting
• The Create>Engage>Sell prospecting framework
• Why it’s difficult to change the old way of selling
• The modern way to compensate SDRs

The #1 reason most prospecting attempts fail

While good prospecting feels natural and doesn’t feel like a sales outreach, examples of bad prospecting are everywhere around us—and they stick out like a sore thumb.

Collin cites two experiences of bad prospecting in the podcast:

Someone reached out to me recently—and the timing of it is what makes it so good. The person offered me a way to make the website better. They clearly put a lot of effort into it, which I appreciated. But the problem was, it was just in the wrong direction.

What the sales rep didn’t know was that Collin had just finished building a website on his own—which he was obviously very proud of. Check out the website below, it’s pretty neat.

What’s interesting to notice in this example is that the salesperson used personalization in their outreach. They did the basic amount of research before reaching out—which is much better than spraying and praying sales tactics.

But what killed the prospecting experience for Collin is that the person made all the wrong assumptions about who he was.

Had the person started the conversation by offering some meaningful compliment or asked a question—that would have been a different conversation altogether. If the sales rep had emailed Collin saying:

Hey, I really like your new website. I saw what you did there. Did you do it all by yourself?

..things would have been completely different. But the assumption that they could “make the website better” implied that Collin did a bad job of building the website. Not a great first impression to make on a prospect.

Unfortunately, we see this happen a lot everywhere around us. Personal trainers reach out to us promising to help you get in perfect shape—falsely assuming that you are out of shape. Imagine what kind of impression you would make sending an email like that to a person who worked hard to lose 100 lbs in the last six months.

You are probably telling them that they look bad despite all the hard work they put into it.

Sales reps in B2B SaaS do it all the time—they will send you a connection request on LinkedIn and send you an InMail as soon as you accept it pitching you their product. They don’t even try to make an attempt to understand if you need their solution.

Lately, there’s another trend in B2B sales prospecting where SDRs don’t ask you if you have time or if they can schedule a meeting to chat. Instead, they will position a soft-interest call-to-action (CTA) asking you if something that they have interests you.

But that’s just bad prospecting disguised as an opt-in CTA. It still puts you, the rep, at the center of the conversation—not the buyers. And it still falls flat on its face.

Thinking about booking a meeting with prospects all the time is the reason you’re failing. That’s not prospecting—that’s pushing meetings on people. Prospecting is reaching out to people with the sole intention of finding people who might actually need what you have to offer. Only at that point can you consider the likelihood of a meeting.

The anatomy of a good prospecting

Good prospecting is cautious. It makes you feel that the person reaching out to you actually cares about you. Good sales prospecting isn’t based on generalized assumptions.

When you make wild assumptions, you subconsciously tell the prospects that you don’t really care about them. You just care about getting a meeting and closing the deal. If you actually cared, you won’t lead with an assumption.

Good prospecting shares a lot of tactics that you can find in dating culture—a domain that’s several orders of magnitude more complex than selling.

You don’t go to a bar and approach a person asking them to marry you. Instead, you most likely will say, “Hi, you look beautiful. Can I buy you a drink?”

And if they reciprocate your move, they might agree and engage in a conversation that can lead to a fruitful relationship. That’s how it normally happens.

But people do the opposite in sales every day—they ask prospects who they don’t even know to “marry them” (i.e. be their customers) in the first-ever interaction. Here’s Collin again on why bad prospecting is earning the sales fraternity a bad rap:

We don’t really care when prospects walk away because we send the same message to 5000 people at once. We only care about the people who respond. That’s a problem because it compounds—it’s why people hate talking to salespeople. We have done this to ourselves.

Good prospecting doesn’t allow you to jump into a pitch and drop your calendar link in the email. It demands that you act like a human—it encourages you to do something that the prospects can’t predict. Like practicing thoughtful scheduling habits.

Give them a genuine compliment, comment on their LinkedIn post to give them a new perspective, make an intro with a helpful person from your network, etc.

Buyers today are aware that most sales pitches are coming from a template—an automated sales cadence in HubSpot or Outreach that lacks empathy. And buyers are numb to it.

Sure, you can use these tools to speed up your sales processes and scale your outreach program. But over time, the heavily templated pitches bring down the efficacy of your sales process. No matter what AI-based tool you are using, you can’t replace the need for genuine human touch.

Technically speaking, all AI does is replicate what humans are already doing—but much faster. The irony is, buyers already hate most of what salespeople do. You can’t take AI and make it better—it will only amplify the worse.

If we fundamentally change the way we sell, it will take AI a long time to catch up to that. In that sense, good prospecting means thinking about how we can make things better at a human level.

The Create>Engage>Sell framework

Among many of the projects Collin is working on right now, he is putting up a sales training program together to help ambitious sales professionals drastically change the way they approach prospecting.

The program suggests a three-step process that he calls the Create>Engage>Sell Framework. It’s basically a principle that encourages you to create relevant content and engage with prospects before you sell them your product. Here’s how it works.

Create

Creating content is becoming an increasingly important part of an SDR’s job. But you shouldn’t create content just for the sake of it. The first rule of social selling is: if you are not an expert on a product, you probably shouldn’t be selling it.

Most SDRs and AEs are young and fresh into their sales careers. They don’t have a lot of experience in sales like a VP to create insightful content on social media. Many of them have no clue about what to post on LinkedIn, how to build relationships, or how to engage with prospects.

The good news is—you don’t have to let that stop you from creating content that can attract the right kind of prospects. It’s easy to come up with your own LinkedIn content strategy to make your social selling more effective. You basically need 5–6 content themes and create content around that. Here’s what Yaag, Avoma’s Director of Content Marketing, suggests to SDRs:

In real life, none of us speak about the same topic all the time. Our online presence needs to be an extension of who we are. One way to approach this is to create content themes and extend them to specific topics that you are comfortable talking about or that represent your brand.

Collin offers similar advice but encourages reps to pick a category. That doesn’t mean you have to sell or talk about the same product for the rest of your sales career. You can pick a category or industry that you are passionate about.

Maybe you are an SDR for a SaaS company but you are interested in managing personal finance. That’s perfect. Create content that can help your target buyers manage their finances better.

But if you create content on real estate software for a year because that’s what you are selling and you then jump into HR tech or B2C SaaS, you will have to start all over again.

In today’s fast-moving world of B2B sales, you’re probably going to bounce around from one company to another every few years. Develop expertise in a category so that it’s easy for you to relate to the same audience no matter where or what you end up in your next stint.

The key here is to realize that social selling is not just helpful for your company—but yourself. No one owns your social media except you, but you will have to put in the time to make it work for you.

The beautiful thing about social selling is that you can use it at work while getting paid, but it’s something you get to take with you to the next stage of your career.

If you are not sure how to get started, Collin has a simple advice: just start doing it. 

He attributes this mantra to Think Media, a team of content creators on YouTube with over 2.35 million subscribers. The folks at Think Media begin all of their videos with an audio intro that says, “you gotta just press record.” And that’s the point.

The great thing about this piece of advice is that no one is going to see the worst piece of content you will ever create (social media algorithms usually punish bad content and bury them in obscurity). So don’t overthink it.

If you don’t have a lot of ideas for creating original content, start commenting on other people’s posts on LinkedIn. Not everything you do has to be your own. The topic you want to speak on is already out there, you just need to build something on top of it.

Here’s what Collin said about getting out of writer’s block:

When I have writer’s block about posting on LinkedIn, I don’t worry about it. I go into the feed and start looking for stuff I can comment on. And before you know it, you will have something in your head that you want to go deeper into and then go write a post.

Nobody is born a thought leader. You become an expert when you start putting your work in public and improving on your ideas. So even if you are on your journey of learning about a new domain or mastering a new skill—share those learnings on LinkedIn in a way that helps others.

Here’s an example of how Sam Bettencourt, Avoma’s lone wolf SDR does it on LinkedIn:

 Engage

If you can comment meaningfully on the right people’s posts on LinkedIn, it’s a lot easier for you to engage the right kind of prospects. The person who created the post will want to chime in on it while you are also expanding your pool of visibility to similar other prospects who are in that person’s social network.

But you have to be thoughtful about commenting on other people’s posts because most people can smell that it’s coming out of a social selling playbook.

If you don’t have a meaningful comment to offer—ask questions instead. If you don’t agree with the post someone has made, challenge them in a civil way. That would still come across as a genuine attempt to engage meaningfully than engaging for the sake of it.

Many sales reps make the mistake of trying to force an angle for them to advertise their product. And it’s fine once in a while as long as you make it interesting. But it bothers people if all you can talk about is the product you sell. The reality is that you can provide value to engage the audience without talking about the product.

Have a good mix of topics you are passionate about, topics that are valuable for your prospects, and topics that are related to the product that you are selling. Meet in the middle somewhere. 

Collin does this beautifully by offering sales reps—his core target audience—advice on how to manage their personal finance because that’s what he is passionate about outside of sales.

Sell

It’s easier to sell if you are creating good, relevant content and engaging with the right people. In today’s age of social selling, sales reps that are good at social media are the ones who are most successful at their craft.

Here’s Sam at it again, speaking directly from his own rich experience as a relentless SDR:

They are less focused on blasting out thousands of emails and far more focused on engaging with their target audience—whether it’s through sharing content or commenting on other people’s content. The great outreach today is super-organic.

It all goes back to the dating analogy we discussed earlier. In the dating scene, the great socializers have several people asking them out every day. They have more options because they don’t go to a bar with the mindset to ask out 20 people each night. Instead, they have the mindset to be happy, to enjoy talking to and meeting people in general—and they are just out doing that.

Most salespeople forget the aspect of approaching sales socially and just focus on making the sales process better. You have to make social selling work organically for you. When you approach it from the mindset of having to hit a certain number, quota, etc. the buyers will feel that in your interaction.

Sales managers can change this by incentivizing realistic behaviors. Perhaps they can get rid of the quota system for SDRs altogether. Maybe they can set incentives for SDRs on whatever they want next in their career. Or perhaps they can just hire SDRs to make it through a year.

Collin suggests SDRs distance themselves from the concept of booking meetings and start building the mindset of a marketer.

Think of content marketers who are really looking to engage. They want to put stuff out there and they are looking to be organic. If you add that with the concept of being a salesperson who actually talks to people and engages with them, the rest is easy.

Why is it difficult to change the old way of selling?

To understand why it’s so hard to break out of the traditional sales mentality, we first need to understand what’s wrong with the traditional sales that was there before social media came.

Before social selling, traditional sales was heavily skewed toward making money. Everything that we did as a sales team is centered around money—not customers or their actual needs. Think about it: if you are in a B2B SaaS startup, you don’t work for a company that the founders necessarily own. The business is part of a massive ecosystem and you need to understand the investment side of it.

Generally speaking, money is the main focus for most businesses because of the market economics at play. Businesses want to raise money and there are investors willing to pump money into promising ventures. They will help you get your company’s valuation up. The understanding there is pretty simple: you start a company, create some company shares, and then make those shares worth millions for the investors to get their investments back.

From a customer experience point of view, that’s a problem because it doesn’t necessarily translate to value for the end customers. It doesn’t even equate to profit.

But the economy is cyclical—venture capitalists (VCs) pour money like water during the boom periods while they make massive cutbacks during the bust periods. VCs also don’t invest in just one company.

Frankly speaking, they aren’t even crazy about the success of your company because it’s one of the many companies in their investment portfolio. In reality, they are betting on just one or two startups to take off and turn into Unicorns.

Many sales teams continue to run ineffective sales processes and mass blast email cadences because they are operating in a system that’s set up to become an investment vessel. They run on old-school investment formula:

Put X number of $ into this fund > investment in 20 different companies > expect 1–2 of them to succeed.

The problem with that formula is that investors are setting up 18 of those companies to fail—and with that, every 50–100 employees who work there to go down with it.

It will take a long time for us to change the industry-standard, VC-suggested sales model because we work in a system that has been perfected over time to deliver the results in a very specific way.

When somebody comes in and tries to make drastic changes in the way selling is done, they will get a lot of pushback. It’s because they are going against a system that’s working—for the investors.

The hesitation is understandable if you think about it from the investors’ point of view. VCs have their own share of pressure to handle because they borrowed money from other people to invest in startups.

That’s precisely the reason why they are generally very scared when visionary founders and sales leaders talk about flipping the old sales funnel upside down or drastically changing the go-to-market strategy.

Transitioning from dollars to value

One of the biggest shifts that’s happening in B2B right now is the transition from dollars to value. The two are still correlated, but the mindset is changing. Now, if you want dollars—you first have to deliver the value. It’s the transition that you can see play out everywhere you look.

Ten years back, you couldn’t have imagined a startup getting 20 million users to sign up for their product without any push from salespeople. But Slack did it—it launched in 2009 and became the fastest-growing SaaS startup in history, acquiring 200K paid users and becoming valued at  $2.8 billion within the first three years of its inception.

Now, we are already seeing lots of SaaS companies mimicking Slack's playbook of leveraging product-led growth. Eventually, we will get to a point where it becomes the new and alternative path to growing a SaaS business.

At Avoma, we did something very different. Instead of choosing between traditional sales and product-led growth, we straddled on product-led and sales-driven strategies to grow Avoma to what it is today.

On a side note, if you want to know more about how we built a product-led and sales assisted model, this might be an interesting read: 

For what it’s worth, we are probably witnessing the beginning of the end of the traditional sales model. If there is any plus side to being in a recession, it’s the changes that it forces on the world. First, it was the COVID-19 pandemic and now it’s the recession that’s making the same VCs change their tone. Today, investors are open to seeing startup founders experiment with new growth models.

This is an opportunity for business leaders to bring meaningful changes. If you as a founder or sales leader have big ideas that can make big splashes, this is the time to implement them because of the low level of resistance right now. The VCs are completely okay to have these brainstorms as long as they help them save costs and ensure returns.

New ways to compensate SDRs in the modern world

Collin argues that the role of SDRs is closer to a marketer than a salesperson. Forward-looking sales teams should redefine the jobs of SDRs into a hybrid of sales and marketing—they exhibit content marketing expertise while still talking to prospects daily.

But it’s a new role altogether. Unlike marketers, they shouldn’t just push out content and disappear. As opposed to their traditional sales roles, they shouldn’t just focus on cranking out a routine list of leads that lack intent or context. Instead, they do a little bit of both but more organically.

That doesn’t mean you give them a mandate of writing 20 LinkedIn posts every day because that would mean you will probably end up getting 20 garbage posts. If you push them down the traditional sales path, you will circle back to the same efficient results.

As for compensating the SDRs from this perspective, there’s no one-size-fits-all answer. One option is to offer them a fixed base salary straight out of the gates and set an annual bonus that they get based on their contributions. This way, you can incentivize them to generate more leads while having an entire year to see what they are capable of contributing.

It also depends on what kind of product you are selling, how transactional it is, and what are your sales goals. If you sell SaaS like you are selling newspaper subscriptions in 1995, it’s easy because all the SDRs have to do is make 500 calls a day and sell at least 50 subscriptions.

The more transactional your product is, the more rigid the sales process gets. But if there’s compounding value in what you sell, you have to spend time building social capital among your target audience.

If you want to change things up, you really need to believe in this new model working out. You have to go all in and decide to pay your SDRs the same way you pay the marketers. Pay them a quarterly bonus just like you give marketers a bonus when you hit your quarterly revenue targets. And fire them if they don’t deliver on their results—just like how you evaluate marketers on their performance.

SDRs are primarily responsible for generating demand and new leads—they are already doing several things similar to marketing. It makes sense to extend the scope of their roles to semi-marketers and encourage them to create content and build a social presence.

Let’s face it—the 10–15% commission that SDRs get for each sale is not much. It’s much easier to pay them a base salary of $60–70K (whatever the going rate is in your industry) and entirely wipe off the commission model.

Start looking at SDRs as marketing roles and evaluate their performance qualitatively. This model has been working perfectly in marketing for several decades now, it most likely will work for SDRs too.