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- Analysing Rippling's Cold Email Outbound
Analysing Rippling's Cold Email Outbound
Tips on how to make cold email work
Insights from today’s article:
🗺️ What Does Cold Email Look Like in 2024? Cold email used to be cheap, predictable and scalable. AI is now flooding inboxes of prospects meaning response rates are dropping. We dive into the issues.
💰 How Best-in-Class Startups are Getting Response Rates: Case studies on how the best are using intent signals, personalisation and competitor research to continue getting results.
Your Feedback: I’ve been thinking about launching a podcast, so what would you like to hear about?
A few weeks ago I started receiving cold emails from Rippling and decided to break down their cold email as the channel has been incredibly scalable and cost effective for the past few years but results for most teams are now starting to deteriorate
This is for a few key reasons:
Companies like Instantly make setting up cold email campaigns easy and now execs are flooded with them.
AI is making basic personalisation trivial meaning it’s getting harder to stand out.
Every outbound team seems to buy the same leads from Apollo, which are old and have been sold to countless teams meaning you’re hitting the same prospects as your competitors.
With all of these problems let’s examine the good and bad of their campaign, before digging into how you could potentially better run an outbound campaign.
Rippling’s Cold Email Strategy
“Hey Henry, Whether you’re ready to switch HR & Finance systems or not, it doesn’t hurt to check out the latest technology so you know what’s out there when the right time comes.
For what it’s worth, we’re now the #1 rated HR platform on every review site (Google us!). We were also named the #1Best HR software by US News, USA Today, Nerdwallet, and so on.
If you’re on the fence, let’s chat. No expectations - you can share your top priorities this year, and I’ll show you how Rippling can help.”
✅ Not too salesy: I like this, at least they’re not asking for marriage on the first date unlike many others.
✅ Good Social Proof: By showing they’re #1 on every review site they demonstrate they’re clear leaders, they haven’t just gamed one site. They used to have a super cool trick to getting social proof by offering anyone who completed onboarding a $50 gift voucher to review Rippling.
✅ They’ve only sent 3 emails. This is key! Whilst you’d previously be fine to send multi-email automations Google’s new spam rules means this is now best practice.
❌ What Makes Them Different: Most companies already have some system in place for HR so you need to convince people what makes you different. Most execs don’t know the USPs of all HR platforms so why would they respond without understanding the benefits to switching.
❌ No Value, Just a Sales Email: This is a pretty obvious pitch, and that’s fine. But as execs get flooded with more of this mass outbound the only way to stand out is by actually providing value.
I got so fed up that for Pricepoint, I spend 1-2 hours researching and doing UI mockups for every single company I message, showing how they could improve their monetisation.

Let’s have a look at the next.
Email 2
“Hey Henry, I just chatted with our CFO Adam Swiecicki, who used to pay for completely different systems to manage expenses (Expensify), bill pay (Bill.com), travel (Concur), payroll (ADP), HR (BambooHR), and IT (Okta).
Adam switched to Rippling and was able to cut costs by consolidating all of those systems into one.
One of his favourite use cases is that he could easily monitor all of the licenses his team paid for 3rd parties (like Tableau, Salesforce etc.) and point out how many employees are using them.
Turns out he loved the product so much he decided to join Rippling as CFO.”
✅ No links in Email: A lot of people fall into the trap of trying to get people to book a meeting immediately. This is a pretty huge red flag for Google and will quickly get you marked as spam. Glad to see Rippling isn't making this mistake.
❌ Bad Social Proof: Colour me sceptical but I don’t really trust the testimonial of the CFO of Rippling to sell Rippling… and I’m not alone. Gong data shows that trying to use non-personalised social proof drops win rates 47%!

An easy way to improve this is to segment your list by number of employees and then the job role you’re emailing. The Head of HR at Facebook has much different needs than a CFO at a 10-person startup in B2B SaaS.
Tailor the social proof to show people in their industry are adopting and it feels more personalised whilst generating FOMO.
Email 3
“Forrester did an analysis on Rippling and showed an ROI of 136% with an NPV of $582K (here is a 1-page summary we made for you!).
I understand these analyses and outcomes don’t fit every company perfectly, and I would love to dig deeper into how Rippling can help Pricepoint achieve its big goals.
How is next Monday some time in the afternoon?”
✅ Consultative: This email is pretty good! It comes across as helpful and they admit that each company gets different results which instantly develops a bit more trust.
How to Improve It
✅ Tailored Lead Lists: If you’re just starting out with outbound don’t just buy a list of leads and blast cold emails out. To boost response & win rates Brex built momentum by first selling to friends, then YC batch mates and then blasting all marketing to one tight geography (SF) meaning they bombarded their prospects with messaging and made it feel like everyone else in SF was using them.
✅ Company Based Personalisation: Individual-based personalisation (e.g. here’s what we have in common) doesn’t really work with execs. They’re busy and don’t care about a random sales rep, but they do care if someone can help fix a problem. That’s why company-based prospecting gets triple the response rate.

One key way to do this? Intent signals.
✅ Scrape Intent Signals: 80% of the purchasing decision for B2B software happens before the prospect reaches out, often researching online before coming up with a shortlist of 3-5 vendors.
To beat competition it’s critical to figure out when a prospect is in the research phase and to help them understand the market and your USPs before they start chatting with competitors, which is where intent signals come in.
These are publicly available signals to suggest someone is in the buying process.
For my company Pricepoint, where we help companies improve monetisation we have a few methods:
LinkedIn Jobs: Companies hiring Head of Pricing, Growth Team or similar
Website Changes: Has the company made changes to improve monetisation (e.g. conversion focused tests or changes to pricing pages in the past 12 months)

We’re able to reach out to companies we know are interested in the service we offer, instead of blindly sending out emails. It means we can provide personalised value to them which results in massively better response rates.
✅ Competitor NPS Surveys: This is an insanely powerful tool we use for some clients. Whilst it’s a lot of work to convince a competitor’s client to switch it can be done.
First, collect a list of clients your competitor has (e.g. from your lost deals) and the end users of the product via LinkedIn.
Send them an unbranded NPS survey asking how happy they are with ‘Provider X’, what features they love and most importantly, what things they hate.
Those customers who signal they’re unhappy? You now have the exact language to for your cold email scripts and how to tailor ads to them.
Seriously, give it a go or send me an email and I’ll run you through how to do it.
Here’s a slide from a client deck:

That’s it for today folks, hope you enjoyed!