Solving buyer pain points in email flows

I’ve trained hundreds of sales reps over my career. Here’s the exact framework I use to write good cold emails from start to finish: 1. Lead with the pain not the pitch The goal of a cold email is to start a conversation, not close the deal. It’s to reflect back a real pain your buyer is already feeling often before they’ve articulated it themselves. No one cares about your product. Especially not in the first touch. They care about themselves and their problems. The biggest mistake I see reps make is trying to close too early. They shove value props, case studies, feature sets, and “we help companies like…” I always come back to this: “No pain, no gain, no demo train.” You’re not here to educate. You’re here to trigger recognition. To make them nod and go: “Yeah, we’re feeling that.” 1. Write like a human The best cold emails don’t have long intros. No “hope this finds you well.” Just a clear, honest attempt to connect over something they care about. Let’s say we’re targeting agencies running 10+ client accounts. Here’s how I’d start: “Hey — I saw you’re managing multiple clients. Curious if you’ve had to deal with deliverability issues lately, especially with the new Google/Microsoft changes. Is this on your radar?” That’s it. No pitch. No product. Just a relevant question that hits a live pain. You don’t need clever. You need to be clear. 1. Structure matters (but keep it stupid simple) I’m not into formulas. You don’t need a 7-step framework to write a good email. You need to understand the buyer and speak to them like a peer. Think about it like this: Line 1: Show you’ve done your homework. Line 2: Bring up a real, relevant pain. Line 3: Ask a question that invites a reply — not “yes.” If your email looks like a blog post, you’re doing it wrong. The goal isn’t to explain. The goal is to start a conversation. 1. Use follow-ups to build narrative (not nag) Most follow-ups sound like this: “Just bumping this to the top of your inbox.” “Not sure if you saw my last message.” Useless. Instead, think of your cold email sequence as a way to diagnose pain over time. Email 1 brings up the initial problem. Email 2 digs into what happens if it doesn’t get solved. Email 3 introduces that you might have a solution, if they’re open to it. Each message earns attention and adds value. Follow-ups shouldn’t be annoying. TAKEAWAY Conversations > conversions. Relevancy always wins.

Every rep on your team can explain what your product does. Half can explain the benefits. Maybe three can explain why it matters to the person they're talking to right now. That's the problem. Almost nobody connects the dots to show buyers why any of this actually matters to their specific situation. Features: Our platform has advanced analytics.  Benefits: You can track performance metrics in real-time. So What: And...? Why does that matter to this particular buyer? Kimberly Pencille Collins from #samsales Consulting laid out a framework during a Sales Assembly course this week that forces you to answer six questions before you're allowed to send an email: Question 1: What challenge is this buyer facing? Not generic pain points. Specific, day-to-day frustrations for this persona in this role at this company size. Question 2: Why is it happening? This is where you prove you understand their landscape. Not just what's broken, but why it's broken. This is your insight moment. Question 3: What happens if they do nothing? Cost of inaction. Make the status quo intolerable. What do they lose by staying put? Question 4: What do you actually do? Not "we make your life better" - tangible, concrete, specific. Are you consultants? Tech? Services? Tell them. Question 5: How does this solve the problem? Connect what you do directly back to the challenge you laid out in question one. Question 6: So what does this mean for them? This is where most reps stop too early. You've explained the solution, now connect it to their actual life. "Your teams will be able to create a playbook of simple plays that keep the pipeline ticking while you nurture difficult buyers." That last sentence isn't a feature. It's not a benefit. It's RELIEF from a specific anxiety that VP of Sales has about pipeline coverage. The exercise creates longer emails initially. You can edit down later. But you HAVE to answer all six questions or you're just throwing features at people who aren't thinking about your solution right now. Kimberly's point: This is your mortar. The messaging you're fed from marketing is your bricks. This framework is how you bring it together and become a consultative seller instead of a walking product brochure. Try this on your next three cold emails. Answer all six questions. See what changes.

Buyers get 100+ sales messages a week. Sellers reach out during budget freeze, text without permission, and spell names wrong. Then wonder why no one responds. 4 things buyers wish you understood (with fixes for each): 1.) I'm only buying 3-5 weeks per year. Find those weeks. You message me all year. But I only research solutions when I have budget approved and a project kicks off. That's maybe 3-5 weeks total. The other 47 weeks? You're mostly just noise. Intent data shows when accounts spike research across multiple related topics. That's when I'm actually in market. Not when you have a quota to hit. Fix: Monitor intent signals across 3-5 related topics. Set minimum match strength to Strong if using Seamless. Contact within 72 hours of a spike. Stop prospecting on your schedule, starting doing it on mine. 2.) Only 21% of you actually personalize. The rest BS me. "I see you're in SaaS" isn't personalization. Neither is my name in a merge field. I use 47 tools in my stack. We just launched in 3 new markets. Our CEO announced a pivot last month. You mentioned none of it. Fix: Your first line must reference something only research would reveal. Pull my exact Intent Topics trending now. Reference recent funding, launches, or expansions. My LinkedIn bio I haven’t updated since 2023 doesn't count. 3.) Stop pushing demos. I need PROOF you've solved this before. You want a meeting before I know if you've helped companies like mine. But I need evidence first. Which similar companies? What specific problems? What measurable outcomes? Without proof, your demo is just features. Fix: Lead with 1-2 case studies matching my industry, company size, and problem. Include hard numbers. "We helped X reduce Y by 47%" beats "Can I show you a demo?" every time. 4.) You sell to one person. I buy with five. You single-thread through whoever responds first. But I have Finance checking budget, Security reviewing compliance, Operations assessing implementation. They all have veto power. Ignoring them guarantees a stalled deal. Fix: Pull the full committee upfront. Say "We typically see RevOps and Security weigh in." Map what each role cares about. Provide role-specific proof. Give me a one-page evaluation plan with milestones and owners. Sellers who book meetings aren't better at selling. They just know when buyers are actually buying.

Cold email isn’t dead. But your playbook probably is. If you’re still blasting 5k contacts with HTML emails from a list you scraped last quarter… that’s why your reply rate sucks. Cold email has changed more in the last 12 months than in the 5 years before it. The rules? Completely rewritten. Buyers are smarter. Inbox filters are brutal. And spray-and-pray isn’t just ineffective - it’s dangerous. I’ve helped many companies drive pipeline through outbound. And in 2025, this is what works: 1. Precision over volume Smaller, segmented, cleaner lists. Built around ICP + signals - not assumptions. If you can’t tell why someone’s getting an email, don’t hit send. 2. Signals over personas Personas are a nice start. But triggers are what convert: • new exec hire • new tech installed • spike in web traffic • job post hinting at pain • funding round with no sales headcount 3. Deliverability as a first priority Great copy means nothing if your emails don’t land. That means: • Google / Outlook inboxes • no images • no HTML • no links and yes - validation before every send. 4. First lines that earn the read “Hope you’re doing well” = delete. Reffering to their pain points = read. Or at least you increase your chances. If your opener doesn’t prove relevance, they’ll never read the CTA. 5. Follow-ups that add value “Just bumping this” doesn’t work anymore. But a follow-up that includes a relevant insight, short case study, or referral angle? That gets responses. 6. Replies, not opens Open rates are a vanity metric. Positive replies and booked meetings are the goal. If it’s not intent-based, don’t track it. 7. Fewer tools, better stack You don’t need 20 tools.  You need 5 that talk to each other. Here’s a lean outbound stack that’s working right now: • Clay (enrichment, scoring, personalization) • Sales Navigator (data) • LeadMagic (validation) • Instantly.ai / Woodpecker.co (sequencing) • GPT / Perplexity (copy generation) I’ve baked all of this into a 2025 cold email cheat sheet. This will save you hours of guesswork - and probably save your domain too. Enjoy!

The best flows don’t feel like marketing. They feel like customer service. Most brands over design and under serve. You don’t need more animations. You need more empathy. Here’s a flow worth copying: Subject: “How can we make this better for you?” Email 1: Ask what almost made them not buy → Multiple choice response Email 2: Tailored message based on their reason • “If shipping speed was the issue…” • “If product confusion held you back…” • “If price made you hesitate…” This does 3 things: • Rebuilds trust • Gathers VOC data • Nudges hesitant buyers without begging Marketing that feels like help will always outperform marketing that sounds like hype.

If you're getting 2%+ reply rates but most responses are "not interested," don't blame your cold email agency. You have a different problem entirely: This is one of the most common replies we coach our clients on at Leadbird. And frankly, it's the most frustrating for founders to hear. When you're getting high reply rates but everyone's saying they're not interested, that's actually good news for your deliverability. It means your emails are landing in inboxes and people are engaging. The bad news is you have an offer issue. Think about it logically: - You've identified your target market. - You're reaching them successfully. - They're responding to your outreach. …but they're rejecting what you're selling. That's not an execution problem…but it is a product-market fit problem. Here, you must ask: Why aren't they interested? This is your identified target market rejecting your identified solution. That should make you examine whether you're solving a big enough problem or whether you're targeting the right people. To improve your offer: 1. Add a guarantee / stronger guarantee if you have one. 2. Ask your 3 best case studies for video interviews. 3. Tie it to a massive pain point 4. Angle it so that it makes or saves them money. 5. Tie targeting to your own social proof. Don't blame the messenger when the message isn't resonating.