Outbound Is Broken. Here’s Why (and How To Fix It).

Outbound sales is broken: it fails businesses, salespeople, and customers. The human touch is gone, reduced to a numbers game. Burnout, damaged reputations, and lost customers follow. But AI offers a chance to fix it.

Gautam Rishi

The way we do outbound today isn’t working.

Not for businesses. Not for salespeople. And certainly not for customers.

As someone who’s dedicated my career to building and scaling outbound sales teams, it brings me no joy to say this. Done right, outbound is a fantastic way to grow a business.

Targeting is precise, feedback is immediate, and it can easily generate a noticeable impact on pipeline for relatively little cost. It should be a pillar of every B2B company’s go-to-market strategy.

But modern outbound sales ignores the human-to-human interaction essential to any sale. It’s not about connecting with people and helping solve their problems anymore. It’s a numbers game.

This expensive, inefficient approach burns out your salespeople, damages your domain, and turns your best customers away before they’ve even spoken with you.

Outbound is broken. But in the age of AI, it doesn’t need to be.

How did we get here?

Not that long ago, there was no prospecting automation.

Email outreach consisted of one or two messages with manual follow-up. There was way more emphasis on the phone and (shocker) meeting prospects in person.

But then two seismic shifts disrupted enterprise sales:

  1. Software as a service exploded. As one well-funded startup after another rocketed to billion-dollar valuations, SaaS eclipsed the financial and consulting behemoths that had dominated the corporate spotlight for the past two decades.
  2. This boom also signaled the rise of the SDR. You simply weren’t considered a successful SaaS startup if you didn’t have a team of SDRs.

During the SaaS explosion, one category of company with an innovative technology was gearing up to change prospecting forever.

Enter the sequencing tools.

Companies like Outreach and Salesloft took over the market around 2015. Driven by the charismatic evangelism of people like Sam Nelson and Max Altschuler, they quickly exploded into unicorns.

This was the exciting new technology of the time. If your sales org wasn’t quick to adopt it—and the practices they created and encouraged—you risked being left behind.It was the first taste of automation for sales teams.

And it was wildly effective.

This new technology gave salespeople the ability to exponentially increase their reach.

Reps could speak to way more people, experiment with messaging on a far bigger scale, and automatically send 10, 12, 15 messages to a lead across multiple channels.Booking meetings with these new tools and tactics essentially became a sure thing. Junior reps could put a Fortune 500 executive into a sequence and often get, not only a response, but a meeting.

The equation was simple. More SDRs doing more activities equals more booked meetings and, eventually, more closed deals and revenue.

But in sales, nothing is new for long

Sales is an iterative practice. Techniques that started as new and innovative quickly became played out and overused. Prospects got wise, recognizing they were on the receiving end of the tactic du jour, and they zoned out.

Success metrics began to drop, first to single digit then zero-point-something percentage points. The math that powered the whole equation wasn’t checking out.

The quickest solution was to open the floodgates at the top of the funnel to increase the volume of folks coming out the bottom.

Which brings us to the state of outbound today

There is a tremendous amount of pressure on sales teams to increase the volume of their outreach. More activity at the top of the funnel equals more revenue coming out the bottom, right?Reps simply don’t have time for the thoughtful, well-researched, personal approach that modern buyers expect. So instead of crafting truly personalized outreach, reps barrage their prospects with dozens of generic messages hoping that one will stick.

This activity-driven, quantity-over-quality approach to prospecting has created knock-on effects for the companies who rely on outbound to grow, the reps hired to do it, and for the profession of sales itself.

Why modern outbound is bad for business

“Only when the tide goes out do you discover who's been swimming naked.”

This famous Warren Buffet quote has been a favorite among those describing the current economic turbulence the tech industry has found itself in.

While the analogy leaves a lot to be desired, I can’t help but to admit it’s a good description of what’s happening to outbound.

Where’s the pipeline?

If the outbound model I outlined above works, where’s the pipeline to show for it?

It’s not there. If it were, SDRs wouldn’t be the first to go when the layoffs happen. Of course, this is the hardest part of everything happening at the moment: real people losing real jobs.

And SDRs are often the hardest hit. If the volume play worked, that wouldn’t be the case.

There are other consequences affecting businesses, too.

Low deliverability and domain damage

Sending 10,000 automated emails a week is not conducive to a healthy domain.

Email providers pick up on this activity, assume your domain is guilty of spamming, and treat it accordingly.I’ve personally spoken with CEOs whose investor update emails have landed in SPAM and senior salespeople whose proposals don’t make it to potential buyers because their email health is in the toilet.

This doesn’t stop at email, either. These penalties apply to your entire domain. That means all the careful work your marketing team does to build up domain reputation—which is critical for SEO—is put at risk by SDRs engaging in irresponsible sending practices trying to hit their target.

The bar for quality is low

If you checked your inbox right now, chances are you’d have at least one unread cold email that’s probably pretty ordinary.

The vast majority of cold outreach falls into that camp. I’ve touched on the reason already: Reps don’t have time for thoughtful outreach. So the result is all automated, zero personalization, generic, and very deletable.

Outbound is expensive, and it may not work

Outbound at scale requires big, cumbersome teams implementing strategies that are slow to pivot.

The playbook is set, the ICP is fixed. All that SDRs need to do is hit play on the sequences. And half the time it doesn’t work out.

The SDRs that make up these teams are often straight out of school, and require more hand-holding and direction than more experienced reps.

I have a ton of sympathy and respect for SDRs. I started my career as one, and have built multiple outbound sales teams with amazing people. We’re doing them a disservice by forcing them to carry out the outbound playbook as it exists today.

Why modern outbound is bad for sales

Modern outbound sales strategies aren’t just bad for the bottom line.

The quantity-over-quality culture we’ve created also has negative downstream impacts on the profession of sales, and those who practice it.

Today’s prospecting tactics repel customers. But they also repel the smart, ambitious people we hire to do it.

Junior salespeople aren’t learning the craft of sales

At its core, sales is about solving people’s problems.

Yet the entry-level salespeople who are tasked with prospecting for new business aren't even being given the opportunity to learn what their potential customers are up against.

Sales requires the empathy to deeply understand someone’s challenges. The creativity to tie that back to your solution. The intelligence to ask questions to get people thinking. The early years of your sales career should revolve around learning those foundational skills.Instead, most junior reps spend their day manually searching for leads that match a predetermined profile of personas experiencing the same exact problem and adding them to templated sequences with generic catch-all messaging.

Here’s your ICP. Here’s your list of accounts. Here’s our sequencing tool. Go make something happen.

They’re hamstrung with unrealistic activity levels and impossible targets.

They’re not learning the skills they need to progress in their careers.

There’s no room to explore outside of those predefined boundaries.

So reps send the same message to the same persona at the same companies and miss out on both real opportunities, and the opportunity to learn and grow as a sales professional.

We’ve turned SDRs into computers

Modern outbound, and the tools we use to do it, require neither problem solving nor critical thinking.

There’s no thought as to why Company X is more worthy of pursuit than Company Y. Reps are under such crippling pressure to move the needle, they only have time for one course of action—put them both into the same good-enough sequence and move on to the next.

Instead of tapping the creativity and potential of some of the smartest, hungriest, most energetic young professionals out there, we assign them mindless, repetitive tasks that burden them with impossible targets.

And it’s burning them out.

Tech sales is one of the most lucrative and fulfilling vocations available today. But the way we as sales professionals treat our newest practitioners, we risk losing them to different career paths.

Outbound in the age of AI

In the not-so-distant future, there will be 10-person sales teams driving $100M in annual recurring revenue.

There won’t be anything remarkable about these reps. Nothing that separates them from solid sellers by today’s standards. But there’s one factor that will make all the difference.

They’ll be equipped with the greatest technology of our generation: AI.The AI-powered salespeople of tomorrow will generate 10x the output of their modern counterparts. Teams will be lean, decentralized, and empowered by technology.

Pipeline will be automated, consistently booking ICP meetings. Reps will be free to focus on high-value activities like preparing for buyer conversations, tailoring pitches and proposals, and deepening customer relationships.

Junior sales reps will start as full-cycle sellers rather than meeting-booking drones. They’ll start off working tier 3 deals, working their way up to closing top-shelf customers. Or they’ll pivot into management and leadership.The tedious, repetitive busywork that has come to dominate sales as we know it today will be long gone.

That’s what we’re building at OneShot

Our mission at OneShot is to equip every salesperson with an AI-powered sidekick that eliminates all the manual work of finding new customers.

Reps can finally stop wasting time on prospecting tasks that can—and should—be automated and start getting back to actually selling.

The four pillars of our platform cover prospecting from end to end:

  1. Email health: We help you build sound email infrastructure and deliverability best practices so emails go where they’re supposed to: your prospect’s inbox.
  2. Lead sourcing: Machine learning algorithms analyze billions of data points from the best data providers to locate prospects and intent signals that your business cares about.
  3. AI-generated messaging: Built on powerful GPT-4 technology and guided by human intuition, our automated messaging finally makes personalization at scale a reality.
  4. Reinforcement learning: Our intelligent system experiments constantly in the background to help you understand what works and why.

The future of outbound selling is here, and it’s powered by AI. OneShot puts your prospecting on autopilot on one platform. Let us handle the busywork of prospecting so you and your reps can get back to building meaningful relationships with your customers.

Your pipeline will thank you.

To see OneShot in action, you can get a demo right here.

Gautam Rishi

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