5 outbound lessons from Rippling at $350m in ARR
Why outbound is their #1 growth engine
Read time: 5 min
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Rippling hit $350M ARR, and guess what?
$48M ARR of that is coming straight from outbound alone in 2024 (estimation).
But here’s the crazy part:
They only built their outbound SDR team in 2022.
Now it’s their #1 growth engine.
Their SDR team is estimated to generate $41.6M in pipeline per month. Even with a conservative 10% win rate, that’s $4.16M in new ARR every month, or $48M per year in 2024.
What’s on today’s menu?
5 key outbound lessons from Rippling
How to apply them to your own team
Let's get cooking!
5 key outbound lessons from Rippling
1: Waited way too long before building their outbound SDR team
Now they're at $350M+ ARR, and outbound alone is bringing in around $48M (estimation).
Sounds great, right?
But there's a big problem, they only started taking outbound seriously in 2022, after hitting $100M ARR. Until then, they relied almost completely on automated emails and marketing. It worked fine, until suddenly it didn't.
When Rippling hit their growth limit with inbound and programmatic outbound, they panicked. They had no SDR team in place, and suddenly they urgently needed one. They hired Ashley Kelly to build everything from scratch under massive pressure, not exactly the best scenario.
Matt Plank, their CRO, even admitted openly on the 20VC podcast that waiting so long was a huge mistake. His exact words? If you think automated emails or marketing forms alone can scale your business, you've clearly never scaled anything before. He says people claiming outbound is dead are totally wrong.
Today, outbound is Rippling’s #1 growth channel, driving around $48M ARR. But Matt knows they should have started way sooner.
What does it mean for you?
Many companies make this mistake. They think outbound sales can be quickly turned on whenever they're desperate for leads. But in reality, building a solid outbound system takes at least 6-12 months of serious effort. If you wait until you're desperate, you're already too late.
Don’t wait until you’re stuck like Rippling was. If you think you might need outbound next year, start right now. Start 9-12 months before you actually need it. Trying to build outbound when you're already behind is a recipe for disaster.
2: Multi-Tiered Outbound Strategy
They split their prospects into different groups based on how valuable they might be. For the most valuable prospects (Tier 1), they use personalized outreach, an Account-Based SDR doing detailed research, and sending relevant messages. They're getting 3 to 7 times more meetings compared to their programmatic program: the same accounts that used to give them only about 10 demos now give them 30-70.
Rippling does this because these deals are big, each one is worth about $45,000 a year on average in their mid-market segment. With deals this size, it makes sense to spend more money and time per account.
For SMB, and smaller accounts (Tier 2 & 3), they use cheaper methods like automated emails, AI-assisted outreach, with mech SDRs. Sure, the success rate is lower (around 1%), but since it's cheaper, it still makes financial sense.
What does it mean for you?
Segment prospects by potential LTV first. High-value accounts get more personalized attention; lower-value accounts get automated or semi-automated approaches.
Calculate how much you can afford to spend to win a customer based on their deal size. If it’s under $10,000, stick with cheap, scalable methods.
Match your investment level to the potential return.
Track how much you're spending per customer in each segment. Keep it efficient, you don't want to spend a dollar to make less than a dollar.
Watch your sales cycle length. Rippling closes $45,000 deals in about 50-60 days. If your sales cycles are much longer, your costs go up.
3: They Invest BIG in Outbound
You know why Rippling's outbound approach works so well?
Because they treat outbound sales as a real company priority, not just something SDRs do on their own.
Ashley Kelly, their VP of Global SDR, says clearly: "It takes a village to scale outbound. Marketing, sales enablement, and RevOps all need to work together."
In other words, outbound isn't just hiring SDRs and hoping they'll magically get results.
What does it mean for you?
Most companies mess this up badly. They hire SDRs but then don't support them properly. They skip investing in tools, training, or team collaboration. And then they're shocked when the SDR team doesn't deliver.
Stop treating outbound as a small side project. If you really want outbound to succeed, make it a strategic company priority. Invest in tools, enablement, a dedicated ops team, and leadership. Otherwise, your outbound team will never scale, and you'll just waste your money hiring SDRs who can't deliver results because you didn't support them.
4: Their AEs Still Don’t Cold Outreach
They keep their roles very clear: SDRs do all the outbound prospecting, and AEs only focus on closing deals. Most companies don't do this, they tell AEs to find their own outbound deals too. But Rippling’s CRO, Matt Plank, says openly that SDRs are simply better at prospecting, so the longer they keep AEs away from it, the better.
Why does this work for them?
Because outbound prospecting is all about numbers: how many accounts you reach out to, how often, and how effectively you convert these contacts into meetings. SDRs, trained specifically for this, consistently beat AEs at these tasks. Rippling's data shows clearly that when SDRs do prospecting and AEs focus on closing, everyone performs better.
But here's a controversial thought: this setup isn't for everyone. Rippling's outbound SDR team is super efficient, so it works perfectly for them. If your outbound SDR team isn't efficient yet, you probably shouldn't copy Rippling blindly.
What does it mean for you?
If your outbound team starts showing real efficiency, you might want to separate SDR and AE roles clearly. But if your SDRs aren't quite there yet, maybe stick with the AE-generated outbound deals too, but not the same way as SDRs. Look at your market, your sales cycles, and your team's skills carefully. Don't just follow industry standards, find out what actually works for your business. Specialization like Rippling’s can boost performance, but only if your team is ready for it.
5: The SDR Org Reports to the CRO
Basically, they made outbound a top-level priority by placing it right under Matt Plank, their Chief Revenue Officer.
Why is this smart?
Because when outbound reports directly to the CRO, everyone stays focused on the same goal: revenue. It keeps things simple. Ashley Kelly, who runs their SDR team, reports directly to Matt, so pipeline generation and closing deals are completely aligned. No confusion, no conflicting goals.
When your company grows, your team structure needs to support the most important initiatives. If pipeline and revenue generation aren't managed by the same person, things usually get messy.
If you're curious about how Rippling scaled outbound to over $350M ARR, I wrote a detailed breakdown of exactly how they did it.
What's your biggest takeaway from this list?
Let's get cooking!
See you in the next newsletter.
👨🍳 Elric
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Reading this case study could not have come at a better time, as 2 of our SDR'S out of 7 was laid off this week and our manager stepped down. We instantly became SDR orphans, being left to find success on our own with little to no oversight.