14 Lessons I Learned About Outbound in 2024
(And AI)
Read time: 5 min
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As 2024 ends, I’ve been thinking about what this year taught me about outbound. And let me tell you, it’s been a journey.
But let’s address the hot topic: “Outbound is dead.”
Spoiler: It’s not. But the old way of doing it is.
When big names like Sam Jacobs and Jason Lemkin say outbound is “broken” or “dying,” I get where they’re coming from, but I don’t fully agree.
Here’s why outbound gets a bad rep:
SDRs are poorly trained and send irrelevant, lazy messages.
AI floods inboxes with generic emails that no one wants to read.
Yesterday, I was listening to a podcast where Jason Lemkin (SaaStr founder) shared a real message he got from an SDR:
“Dear Jason, will you be at SaaStr today? Let’s meet for coffee.”
Ouch. That’s not outbound, it’s spam and bad targeting.
What’s really happening?
The wrong way of doing outbound is dying.
14 Lessons I Learned About Outbound in 2024
This year, I rebranded to Outbound Kitchen and studied top outbound teams like Rippling, Snowflake, Ramp, Pigment, Triple Whale, and Owner.com. Plus, I worked with amazing customers.
Here’s what stood out:
1. Cold calling is king
With inboxes overloaded by AI-generated emails, cold calling stands out. AI can’t replicate the human touch (yet).
Rippling SDRs book 650 demos monthly, 50% through cold calls.
Nooks SDRs generate 75% of meetings this way.
Owner’s BDRs bring in $72K ARR per month, per rep, 95% from cold calls.
2. AI/ML-Powered Account Scoring
Top teams like Owner.com and Snowflake use ML models to prioritize leads based on win rates, ACV, signals, and low churn rates.
Result?
The GTM team doesn’t waste time. They’re handed the best-fit accounts with solid reasons to reach out.
3. Cutting Non-Pipeline Generating Activities (PGA)
Outbound reps waste too much time on tasks that don’t move the needle—like list-building, researching, or chasing bad numbers.
At Chili Piper, this is a big focus for me. When reps aren’t prospecting, they’re not building pipeline.
Here’s an example:
I worked with a team where SDRs spent 40% of their time on non-PGA tasks. For a team of 10, that’s 160 hours per week wasted.
By cutting out 80% of those tasks, each SDR could add 2 new opportunities per month, that’s 20 new opps per team.
At a $70K ACV, that’s $1.4M in new pipeline per month or $140K ARR at a 10% close rate.
4. Branded Caller ID
Zach Rego (CRO of Triple Whale) took it up a notch:
Every cold call number shows Triple Whale as the caller ID.
Why does this matter? Reps make thousands of calls each month, and every ring becomes “free” advertising. Even if prospects don’t answer, they see the name and start recognizing the brand. It’s a simple way to build familiarity before the conversation even starts.
5. Are outbound teams more efficient: Remote or in-person?
Surprisingly, both can work, it depends on the team and structure.
In-office teams: Pigment, Rippling, and Snowflake
Fully Remote Sales teams: Triple Whale, Nooks, and Owner.com
6. Inbound and outbound? Separate AEs, separate process.
Inbound and outbound require completely different skills and approaches, so top teams split the roles—and the process.
Here’s why:
Inbound AEs handle discovery calls with prospects who are already interested. These leads have visited the website, requested info, and are further down the funnel. The discovery process is straightforward, focusing on questions like BANT or MEDDIC, because these prospects usually know what they want.
Outbound AEs take a different route. Their calls start with education and value. Forget standard discovery, these conversations dig into the prospect’s pain points, why they need to change, and real-world examples of how others are solving similar problems.
7. Prospecting Days (PG Days)
Prospecting Days are a game-changer for building a strong outbound culture, no matter your team size.
Here’s how it works: the whole GTM team (or even the entire company) focuses 100% on generating pipeline for a day. It’s planned in advance, creates momentum, and makes prospecting the top priority. Simple, effective, and a big win for outbound teams.
8. Programmatic Outbound + Account-Based Reps
I used to think programmatic outbound was just for lead gen agencies. Turns out, top teams like Rippling, Ramp, and Pigment are crushing it with this approach.
Here’s how they do it:
Tier 1 accounts get personalized attention from account-based SDRs.
Tier 2 and 3 accounts are hit with programmatic outbound.
Why programmatic outbound works:
Cost-Effective: Scales with a solid database and software—no need for tons of reps.
Massive Reach: Covers your entire TAM with targeted, automated outreach.
Predictable: It’s a numbers game: emails x conversion rate = demos.
9. Outbound SDRs can work for the SMB segment!
Some LinkedIn “experts” say, “Outbound SDRs don’t work for SMBs or ACVs under $30K.”
Well, Owner.com, Rippling, and Ramp would like a word.
Owner.com’s ACV is just $5.5K, and their BDRs are pulling in $72K ARR per month, per rep, all from outbound.
10. Practice Like Pro Athletes
Practicing on prospects? Huge mistake.
You don’t need 10,000 real calls to nail your opener. Role plays, solo practice (even while walking or commuting), or AI tools like ChatGPT can get you there.
The best teams don’t waste good leads on practice, they show up ready. Pro athletes don’t hit the field without prep, and top sales reps shouldn’t either.
11. AEs don’t do cold outreach
AEs shouldn’t waste time on cold outreach. They’re much better off focusing on warm leads, like closed-lost opportunities, customer referrals, exec intros, or investor connections.
Kyle Norton said it best: having AEs work cold accounts is a waste of time and money.
At Rippling, they know their outbound SDRs are better at it, so AEs stick to what converts.
12. Hyper-specialized teams
This one surprised me, top teams don’t rely on full-cycle AEs.
Instead, they break things down:
Outbound SDRs handle cold accounts, customer expansion, and channel partnerships.
Inbound AEs focus on warm leads.
Outbound AEs take care of deals sourced by SDRs.
They even have a data and ops team dedicated to outbound.
It’s all about letting each role specialize and focus on what they do best.
13. Don’t believe in building relationship
Forget the “build relationships” advice you see on LinkedIn, it’s fluff.
Not a single top team I’ve talked to makes “building relationships” their top priority. Instead, they focus on being relevant and having strong business acumen. That’s what drives success in outbound.
14. AI in Outbound
Last December, I thought AI was just for writing cold emails. Turns out, it’s so much more. AI isn’t here to replace SDRs or AEs, it’s here to make them better. It cuts down on admin work and eliminates non-revenue tasks so reps can focus on what really matters: prospecting, and selling.
Study ICP & Personas: Use AI to analyze your ICP and buyer personas, map challenges, and connect them to your product’s impact.
Build Account Lists: Generate targeted account lists by scraping diverse data sources with AI.
Account Scoring: Predictive models help focus on high-potential accounts (we talk about this above).
Find Competitors: Leverage AI tools to quickly identify competitors and launch targeted campaigns.
Contact Data: Simplify finding and validating accurate contact details to speed up outreach.
Knowledge Base/Playbook: Use AI to create accessible, dynamic sales playbooks powered by internal data and transcripts.
Account/Prospect Research: Automate deep prospect research with AI to craft personalized, high-impact outreach.
Update SFDC: FINALLY. SDRs and AEs can stop wasting time on this.
Cold Call Roleplay: Practice realistic cold calls with AI voice simulations to refine skills and build confidence.
Creative ways to book meetings: write analogies, poems, create AI-images, and AI-music.
Account summary: Centralize all relevant account insights by integrating AI with internal and external data sources.
My biggest lesson of 2024
Outbound isn’t dead, and it’s not just about emails or cold calls. It’s about having the right systems, strategy, and focus.
The best teams don’t wing it. They invest in their process, their people, and the tools that make them faster and sharper. They prioritize efficiency and train like pro athletes to stay at the top of their game.
Looking ahead to 2025
I’m excited about predictive account scoring becoming the new standard. It’s a game-changer for targeting the right prospects at the right time.
Next year, I’ll be diving deeper into these lessons and breaking them down so you can test, tweak, and implement them in your own outbound kitchen.
What’s the biggest thing you learned in 2024? And what’s the one thing you’re most excited to try in 2025?
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Yo, this is a great list! A number of points got my brain churning, but I'm especially excited to implement some cold calling into the mix.