Cold email strategies for generating $5M pipeline

Your prospect has 147 unread emails. Yours just got added to the pile. What makes them open YOURS instead of the other 146? After sending thousands of cold emails and generating over $700M in sales throughout my career, I've identified the #1 mistake destroying most cold outreach: ZERO RIGHT PERSONALIZATION. Most reps "spray and pray". Sending the same generic template to 1,000 prospects hoping something sticks. Then they wonder why their response rate is 0.5%. Here's the cold email framework that consistently gets 20%+ response rates:  → Make your subject line about THEM, not you. Use recent news, achievements, or common pain points to spark curiosity. Example: "Your Inc 5000 ranking" or "Austin expansion" 1. Keep your email so simple it doesn't require scrolling. It MUST be mobile friendly, as 68% of executives check email primarily on their phones. 2. Use this 3 part structure:  → Personal opener: "Hey [Name], [specific personalization about them]"  → Show understanding: "In chatting with other [title] in [industry], they're typically running into [pain point]"  → Soft CTA: "Got a few ideas that might help. Open to chat?" 3. Research these personalization sources: • Company website (values, mission page) • Press releases • LinkedIn activity • Earnings transcripts (for public companies) • Review sites The hardest territory to manage isn't your CRM. It's the six inches between your prospect's ears. They don't care about your product. They care about THEMSELVES. Recently, one of my clients was struggling with a 1.2% response rate on cold emails. We implemented this framework, and within 2 weeks they hit 17.4% - with prospects actually THANKING them for the personalized outreach. Find your sweet spot on the personalization spectrum. You can't do hyper personalized video for everyone, but you can't blast the same generic template either. — Hey reps… want another cold email strategy? Go here: https://lnkd.in/gKSzmCda

Some of your future best customers are using competitors today. Here's how to get them to come to you instead. Step 1: Conduct Buyer Research Interview at least 13 current or former competitor customers. Don’t overdo it with more interviews than you need, or you’ll risk diminishing returns. You'll book these quicker if you can incentivize $50 - $100 per interview. In the interview, figure out your buyers’ goals, pain points, and their experience with your competitor to see if you can identify strengths and weaknesses. Step 2: Craft Compelling Messaging Take what you learned from your buyer research and build a message that would make those buyers say, “I want that.” • Keep it simple • Speak their language • Don’t be self-centered (nobody cares about you) • Solve, don’t sell (i.e. explain how your product would make their life better or easier) OK, but how do you bring up the competitor? Lavender 💜 has a great cold email template that lays it out like this: • Acknowledge the competitor • Ask the recipient if they’re happy with it • Compliment the competitor • Highlight the competitor’s shortcomings • Open up a dialogue with a question related to the shortcomings Step 3: Choose Your Campaign Strategy Once you’ve figured out your messaging, it’s time to pick the channels to reach your audience. Map out the flow—when and how will you deliver your message? Some possibilities: Inbound: • Google Ad ➡️ Comparison Landing Page ➡️ Free Trial • Organic posts on LI ➡️ Competitive Webinar Registration ➡️ Dedicated Follow-Up • LinkedIn Ads ➡️ Long-Form Comparison Blog ➡️ Demo CTA Outbound: • Get a list of companies that your competitor shows on their site ➡️ reach out to them • Pull all closed lost opportunities from your CRM that mentioned the competitor ➡️ reach out to the companies if it’s been longer than 6 months to see how things are going Step 4: Offer Irresistible Incentives Switching to a different tool is hard. You’re essentially asking people to change processes, migrate their data, re-integrate with their tech stack, learn a new platform… so be sure to recognize this and account for it when you’re working a rip n’ replace opportunity. Unless your product is truly 10x better than the competitor being used, consider these additional incentives to make a switch to you a no-brainer: • Buyouts (ask for testimonials or case studies in return) • Free trainings (assure your prospect that their team will know how to use your product) • Free migration, implementation, and integrations to remove as much friction as possible TLDR: get creative and think outside the realm of discounts (although, those can help too). Step 5: Test, Measure, Evolve Challenge yourself and your team to put something together in under a month. See what happens. Iterate. Rip n’ replace campaigns are plays that most companies should learn to get good at!

In 27 months, I grew my SaaS startup from $1M-$10M ARR in with only 1 salesperson doing 100% OUTBOUND SALES. Here’s my 7-step playbook for building a lean, high-velocity cold email machine: Step 1) Make sure you have product-market fit - My thesis for 2023 and beyond is without word-of-mouth, nothing will work - But if you have strong word-of-mouth (from PMF), many things can help speed you up, including high-volume, low conversion outbound - which we ran Step 2) Identify your target audience - We used BuiltWith to ID domains who used complimentary tech - We then ran the site traffic with SimilarWeb - For us the winning combination was Shopify + Klaviyo above 10k/mo uniques Step 3) Get creative about getting email addresses - The *lazy* thing to do is pull directly from the data vendors - We find the contacts on Linkedin, then use Skrapp and Hunter to find emails - We would include up to 5 potentially relevant people and copy them all - We sell to the high end of SMB (so we always include CEO as well) Step 4) Create short email sequences - We have used a very similar 3-part sequences for the last 3.5 years - Email 1: Present the main idea. For us, “We can get you email addresses of your anonymous web traffic, even if they don’t fill out a form” - Email 2: Social proof from brands they truly admire (hard in the beginning) - Email 3: A super-simple use case email explaining the actual workflow Step 5) Write clear and simple copy. - Each email should be no longer than a few sentences - Make each sentence its own paragraph - Have no more than one idea per email - Keep it conversational - CTA is a Calendly link in both the body and signature of the email Step 6) Manually send the emails, rather than using automation tools. - We have a team of VA’s in the Philippines manually sending from Gmail - Any response gets routed back to a BDR/AE in the USA - The team in the Philippines also does the lead gen, very manually - Cold email gurus will say this is stupid and sucks, but … scoreboard! Step 7) A/B test the sh*t out of it. - Change something, pick a winner - Try to hone in on things to optimize - You’re building a machine that improves itself It may not work for everybody, but it worked for us. Happy to answer questions in the comments! 👇 TL;DR Step 1) Have Product-Market Fit Step 2) Identify Target Audience Step 3) Get Email Addresses Step 4) Create Short Sequences Step 5) Write Clear/Simple Copy Step 6) Send Manually Step 7) A/B Test

I've booked over 1,000 sales calls using my "1-2 Punch" cold email strategy, and I'm going to break down exactly how it works: Here's the #1 mistake I see in cold emails: People write a 4-paragraph manifesto to prospects who've never heard of them. Product features, company history, client logos - the whole nine yards. You're basically screaming "I'M HERE TO SELL YOU!". And once you show all your cards upfront, your follow-ups have no ammo left. Instead, here's how my 1-2 Punch strategy consistently books calls: Round 1: The Jab 👊 Think of this as your feeler email. Keep it intentionally brief and spark curiosity. "Are you looking for more qualified sales calls each month?" "We can book 10 sales calls on your calendar each month on a pay-per-call basis. Interested?" These work because they're easy to reply to and don't feel "salesy". One powerful sentence is all you need to create curiosity. Round 2: The Right Hook 🥊 THIS is where you unleash everything you were tempted to put in email #1. Here's a real example that landed a $45k deal: "The reason for my email the other day is because we can book 10 calls on your calendar each month on a pay-per-call basis with personalized cold emails. We recently did this for [Company X], and they closed $25k in their first month. We guarantee a minimum of 10 qualified appointments, or you don't pay. Our average client sees a 3.2x ROI within 60 days. Would you like to discuss this approach for [Company Name]?" Perfect timing? Send your Jab on Tuesday/Wednesday morning, wait 48 hours, then throw your Right Hook if there's no response. Two more follow-ups max after that. Implementation is simple: Take your current first email, bump it to email #2, and write a short, punchy opener for your new first email. Then watch your numbers climb. Speaking of numbers: My traditional approach got a 2% meeting book rate. The 1-2 Punch method gets 8%. That's a 4x improvement simply by reordering and restructuring your emails. Real talk: This strategy works because you're playing the long game. You get two chances to connect before revealing your full pitch, and you're not coming across as desperate in email #1. Btw, what's your go-to cold email strategy?

In August, we generated $1.16M in qualified pipeline with cold outbound and only 2 reps. Here's our brand new outbound sales playbook (and the 8-day sequence and scripts we use to book 15 meetings a week): BACKGROUND: In August, I outlined a few changes we were making to HockeyStack's GTM. - Kill Every Program Not Generating Enough Pipeline - Make Pipeline Generation a Team Sport - Set Up Our First Cold Outbound Program Now, the results are in... Despite what the haters say on Linkedin, outbound is FAR FROM dead. We hit a NEW PIPELINE RECORD in August. 25% more pipeline than our previous best month. And a HUGE part of that was our new cold outbound program. Here's our playbook (and what you need in place first to get it right): 1. Ruthlessly Tier Accounts First, Alex Choi analyzed our customer base and the best-fit opportunities. He found firmographic and technology patterns. We then tiered accounts based on this, and we are spending +50% of our time on our GOLDEN TIER. No magic technology with promises of infinite scale (we know our TAM isn’t limitless). Just ruthless focus on accounts we have high confidence HockeyStack can help. 2. Be Fearless on the Phones The script took a ton of iteration, but it was well worth it. Devan Joseph averages 2 qualified meetings per day using cold calls. He's a rockstar. YES, the phone still works. And YES, sometimes we piss off people. But we still book a ton of meetings (get a copy below). 3. Use our Executive LinkedIn profiles We connect with almost everyone we reach out to using exec profiles. Even though it might not be the best time to evaluate HockeyStack, they start seeing our posts every day and when they reach a critical mass of engagement, we reach out to start a conversation. Here's what we needed in place to make this work: 1. Brand Presence When HockeyStack was unknown, I’ve sent THOUSANDS of emails and booked 0 meetings. Now, most people say “I know you from somewhere” when we email or call them. It's easier said than done, but BRAND (aka being well known) is the ultimate outbound accelerant. 2. A Burning Need Tied to ROI If your prospects aren’t saying “THIS IS A PROBLEM FOR US RIGHT NOW” 99% of the time after you pitch them, you need to pivot. The perfect playbook, scripts, sequences, 100s of SDRs, and millions in marketing spend won’t fix this 3. Strong Multi-Channel I'm not just talking about from an outbound perspective (send them an email, call them, and connect with them on Linkedin, etc). But overall sales + marketing alignment. It goes back to point #1. They need to know your name before you show up. Use emails, LI ads, content, social, events, billboards, video, etc. That's the only way they'll remember you, let alone trust you. If you want our exact outbound sequence and the call script, like this post and comment OUTBOUND below. I'll send it to you.