Our Inboxes Need a Reality Check
Every Tuesday, I get over 100 cold emails, and most of them are awful. They’re impersonal, pushy, and sometimes flat-out rude. It’s no wonder outbound gets a bad rap. These messages come from SDRs who are desperately trying to reach their quota.
The one troubling, yet consistent theme I’ve noticed amidst a sea of ineffective outbound messages is that they immediately open with a demand and there is a reason those types of messages doesn’t land well—I as well as all outbound message recipients— do not owe my time to a complete stranger. When follow-up messages become forceful in demanding a response, it makes me less apt to work with that company in the future.
But here’s the truth: outbound works, just not the way you think.

Why Most Outbound Fails Before It Starts
The biggest mistake I see companies make in leveraging their outbound team is treating them as if they are another email automation or one-to-many channel. Clever and creative emails sent at scale are what email automation platforms were built for; this model simply does not work with outbound.
The most impactful and beautiful thing about your business/sales development representatives is that they are a team of humans, capable of human connection, empathy, and tailored messages. This is the secret sauce, and this is what makes an outbound strategy effective.
Throw your Freezer-Burned Cold Calling and Emailing Strategies in the Trash
SDRs are not effective at the top of the funnel. Full stop. They need data to thrive, and that is why they belong on the marketing team, where data drives decisions.
Contacting a complete stranger out of the blue with your value proposition is a waste of time. An outbound message only works when it reaches someone who actually gives a shit about what you have to offer. This means prioritizing quality over quantity. The best outbound messages hit the right person about the right solution at the right time. This can only be achieved by using data to select the right prospects, including:
- Closed/Lost opportunity Data
- Intent data from ABM tools
- Past marketing campaign interactions
- Professional relationships (old clients in new roles, friends of executives)
What Winning Outbound Teams Do Differently
Lead Recovery > Cold Prospecting
In a B2B environment, timing is everything, so even if you have a viable lead, factors such as org chart changes and budget cuts can make these opportunities run cold.
Account executives will always focus their attention on the most viable opportunities in any given pay period so that they can make their commission. Even the most well-intentioned Sales Executive is going to deprioritize follow-up with a stagnant opportunity over closing a hot deal; their compensation packages actually incentivize this behavior.
This leaves room for your BDR team to follow up and recover opportunities when a lead becomes non-responsive or an opportunity is closed-lost due to budget or prioritization issues. BDRs can jump in and give your sales team another “at bat” with an otherwise dead lead.
Share Something Useful First
Instead of reaching out and requesting a meeting in the first interaction, arm your BDRs with an arsenal of educational material from the marketing team, so they can lead with value, rather than asking for something from a perfect stranger. This only works when the content shared is relevant, so you must leverage data to ensure they are sending content that will resonate.
This looks like following up with a person who downloaded a piece of content with a related asset rather than demanding a phone call, or following up with a lead who ghosted with a case study to provide more information. Having a BDR reach out with a piece of education material to a hot lead does two things, first it leads with value rather than demanding something from a cold lead, and we start with an offer. Second, it helps increase the chances that your high-value marketing materials are actually seen by the most attractive leads (and gives you a cookie to fuel retargeting efforts).
The average person receives 120 marketing emails a day. So even the most clever marketing emails are less likely to be seen by your prospects now than they were even five years ago. BDRs can help ensure your most effective content is seen by the right people.
Make Events Irresistible
I’ve found success in filling customer events with a healthy mix of prospects and sales contacts. The secret here is to make the event irresistible, be it an exclusive sporting event or a Michelin-star dinner, so the prospect feels like it’s worth their time. While you can expect more attrition from your RSVP list from prospects compared to customers, aligning prospects with your most engaged customers is a winning recipe so the juice is certainly worth the squeeze.
An exciting event invitation is a great way to lead with value, the more personalized the invitations, the more successful you’ll be in filling these events.
Bonus: Even if your prospect isn’t able to attend, an incredible event invitation is still a great way to start earning trust with these prospects.
Related Content: Discover the secret to my $25M Event Strategy
How to build Your Own Outbound Machine
Better Pipeline Starts with The Best People
The best, most successful BDRs have an extremely high emotional intelligence. These are empathetic people who enjoy connecting with others. After all, modern outbound is not a numbers game; you need someone who understands how to pick a viable connection, find common ground with strangers, and be persistent.
Ditch your Email and Phone Call Quotas
If you want to incentivize your team to craft truly tailored and effective outbound messages, you need to incentivize them accordingly. This means rethinking the traditional quota-based requirements and payment structures.
Invite Them to Marketing Planning Sessions and Include Them in Your Feedback Loops
BDRs actually interact with customers and prospects, so they are an incredible source of feedback when it comes to what content and campaigns resonate with customers. Exposing them to campaign planning also serves as inspiration to help them devise smarter outbound campaigns.
Here’s the Proof
I transformed an outbound program that brought in only one opportunity in a calendar year to a high-performing team that brought in nearly 3 million in pipeline in one year. Same team, with a better strategy and access to data to make their outbound strategies stronger.
Revenue increased from just 18k in Pipeline in 2023 to over $3M in pipeline generated YTD.
Outbound Sourced Pipeline 2023-25
Outbound Sourced Opportunities 2023-25

TL;DR
Outbound works, but only when it connects, and connection requires more than clever copy and a cadence sequence. It takes empathy. Timing. A real understanding of who is on the other end of the message and what they’re navigating in their business. Most outbound programs fail not because people don’t want to talk, but because the message you’re sending them gives them no reason to care.
If you want outbound to work for you, then we have to reframe what it looks like:
- One well-timed, human message will always outperform 1,000 generic ones.
- Follow the breadcrumbs (closed-lost opportunities, intent signals, content downloads)
- Give something before you take. Share something useful.
- You need a viable connection. Make sure your BDRs are the right people for the job.
When we give our teams the data, space, and permission to act like people (not programs), we create something powerful: trust, not just a pipeline.

















