Tips for Timing and Relevance in Outbound Sales

Most reps think they’re “doing outbound.” But their idea of a sequence is 6 emails, zero value, and a few sad bump messages. That’s not prospecting. That’s praying. Meanwhile, my clients are booking meetings with CROs at Fortune 500s — and here’s the sequence they use (10 touchpoints, built to convert): If your pipeline sucks, your sequence probably does too. Most reps don’t get ignored because they’re bad at writing emails. They get ignored because they rely on one channel. Because they give up after 2 touches. Because they confuse “checking in” with “creating urgency.” Here’s how high-performing reps actually break through: 1. The structure: 10 touchpoints across 20 days - 6 emails - 3 phone calls - 1 video on LinkedIn Every message with a purpose. Every channel working together. 2. The content: Stop bumping. Start teaching. Most sequences are noise. They repeat the same CTA (“just checking in!”), offer no insight, and get deleted by day 2. Instead, think in layers: Email 1 = POV tailored to the account Email 2 = Specific ways you help teams like theirs Email 3 = Case study or customer story Email 4 = ROI data, benchmarked Email 5 = Industry whitepaper or third-party research Email 6 = Product demo or experience preview Every email adds value. Even if they never reply, you become unignorable. 3. Phone still works. If you use it right. Don’t cold call. Warm call — immediately after the email drops. Reference your message. Be human. Don’t script. 4. Use LinkedIn like a human Day 1: Send a connection request (no note) Day 4: DM them after they connect Day 14: Drop a short video — selfie style, natural, no script This part matters most. Executives ignore cold emails but they watch DMs that feel real. 5. Automate the follow-up. Never the personalization. Yes, you can load this into Outreach or Salesloft. But if your content sucks, it doesn’t matter. Write once. Reuse the assets. Track opens. Follow up religiously. Be the rep who doesn’t disappear after 2 tries. I’ve helped reps use this exact sequence to book meetings with CROs at F500s. If you want coaching on how to build yours — the right structure, the right messaging, the right mindset — send me a DM. REMEMBER: Most reps fail not because they stop too late. But because they stop too soon. Build a real sequence. Say something worth hearing. And don’t quit at touch #3. This is the way. Be the 1%. Book the meeting.

If Your Product Solves a Problem… Why Doesn’t Your Pitch Sound Like It? "Buyers don’t want to hear what you do. They want to feel the cost of doing nothing." Let that sink in for a minute... The biggest deals don’t die because of price. They die in silence because your pitch didn’t feel urgent. - You showed the features. - You explained the benefits. - You tried to build rapport. But you forgot the most important part... You didn’t make the pain of inaction louder than the comfort of staying the same. Here’s how great sellers create emotional urgency: 1. When Opening the First Conversation ↳ Instead of: “Here’s what we offer.” ↳ Say: “Let me show you what’s quietly costing your business every day.” 2. When Diagnosing Their Needs ↳ Instead of: “What are your goals this year?” ↳ Say: “What’s the real consequence if nothing changes?” 3. When Presenting Your Solution ↳ Instead of: “We can improve this metric.” ↳ Say: “Here’s the exact cost of doing nothing for the next 6 months.” 4. When Facing Price Objections ↳ Instead of: “Let me justify the ROI.” ↳ Say: “Let’s break down what inaction is already costing you and what that looks like a year from now.” 5. When They Ask for Time to Think ↳ Instead of: “Sure, take your time.” ↳ Say: “Let’s set a time to decide, because time is the problem.” 6. When Showing the Demo ↳ Instead of: “Here’s how it works.” ↳ Say: “Here’s the before and after if this problem keeps going.” 7. When You Feel Tempted to Overexplain ↳ Instead of: “Here’s everything we do.” ↳ Say: “Let me show you what you’ll lose if you don’t act.” 8. When You’re Asked “Why Now?” ↳ Instead of: “Because we’re the best in the market.” ↳ Say: “Because you can’t afford to stay here another quarter.” 9. When the Buyer Feels Indecisive ↳ Instead of: “Let me follow up next week.” ↳ Say: “I’ll help you make the clearest decision you’ve made all year, today.” 10. When Closing the Deal ↳ Instead of: “So, are you ready to move forward?” ↳ Say: “What would waiting cost you and who else pays the price?” Great sellers don’t just demonstrate value... - They dramatize the cost of delay. - They don’t just inform. - They emotionally transform. Because people don’t buy when they understand what you do. They buy when they feel what it’s costing them not to... "Lead Different. Sell Smarter. Win with Purpose." --- ♻️ Share this post with a sales leader who needs to hear it. Follow me for more strategies to grow your team and results and drop me a comment about how you manage this process... 👇 👉 Click here: Follow me on LinkedIn: https://lnkd.in/eA7csH2q Join our community of 36,650+ sales professionals today! 👉 Click here: Beyond The Funnel Newsletter https://lnkd.in/ed3iMb8x P.S. Thanks for reading!

In 36 months, I scaled a hunting team at AWS from $0 to $25M Though it was seen as a great success by many, there are 5 critical shifts I’m applying to build a modern outbound engine at Yess: WHO, WHY, WHEN, TO WHOM, and HOW LONG. Here’s the breakdown: 1️⃣ WHO is reaching out: - Old Way: entry-level SDRs flood inboxes with spam. + New Way: Team-selling facilitated by SDRs. Decision makers prefer talking to other decision makers. Executives and peers should engage directly. companies should move from old-school outbound to team selling model that is facilitated by SDRs and driven by signals and intent data. 2️⃣ WHY we're reaching out: - Old Way: Generic emails saying, 'I see you're the {job title}...' + New Way: Relevancy > Generic personalization. Generic outreach that lacks relevance and personalization is dead. Look for accounts that visited your website, engaged with your social media, or showed intent through third-party data to craft contextually rich content driven by intent data and real-time signals. 3️⃣ WHEN we reach out: - Old Way: As soon as a new lead gets into the CRM, no matter what. + New Way: Engaging contacts when they show interest. Sales isn’t about immediately pouncing on every lead anymore. Leading sales teams will strategically time their outreach with behavioral signals, like site visits or content engagement. 4️⃣ To WHOM we are reaching out: - Old Way: Single (ICP) persona within the account. + New Way: Target the entire buying team, with personalized touches. Modern outreach should involve the entire buying committee. Each stakeholder has different needs and goals. Use detailed persona data to create messages that hit home for everyone. 5️⃣ HOW LONG we reach out: - Old Way: same 18-step generic sequence for all accounts. + New Way: Dynamics playbooks based on live engagement data. Dynamic playbooks help sales teams tweak their outreach using live data. Sequences adapt to prospects' actions in real time, keeping the prioritization of accounts updated and dynamic. TAKEAWAY: The outbound paradigm is shifting and pushing us to focus on precision over volume. Outbound should leverage: + WHO is reaching out,  + tailor WHAT they communicate,  + sync it perfectly with WHEN it matters the most, + strategically choose TO WHOM they reach out to,  + and dynamically adjust HOW LONG they engage based on data. Keep them in check. 

Avoid these six mistakes that kill most outreach (from someone who booked 153,000+ sales calls with cold outreach): 1. Lack of research Never send an email or a LinkedIn message without researching the person you’re reaching out to. Do they have a blog? Do they have a new product announcement? What recent events have they been involved in? Did they write a book? Who do they follow on Twitter? Nail down your research. 2. Poor timing Sending an email at the wrong time will lower your chances of getting a reply. Avoid sending emails: → During holidays → Weekends → Early mornings or late nights Emails sent between 10:00 am and 2:00 pm have the highest response rate. 3. Twisty subject lines or intros Avoid making people guess what your email is about. Be direct and clear. Also, never start an outreach email with "I hope this email finds you well." That's a wasted opportunity. Instead, start with something specific to their work or the research you did on them. 4. No proper follow-ups Don't expect prospects to reply to your first email. It takes an average of 4-7 touches to make a sale. According to HubSpot, 44% of people give up after one follow-up. Be the one that doesn't. 5. Ignoring personalization Personalization is the key to breaking through the noise. Use their name in the email. Reference their recent work. Acknowledge something unique about them. Make the message about them, not you. 6. Irrelevant messages (target persona) Target the right people. That's rule #1. Don't waste time with people that have no interest in what you're selling. Design your message for your 'ideal customer persona' and then find the right person at that company who fits that mold. Selling fishing gear to vegetarians isn't a winning strategy. 7. Trying to sell too soon Your goal of an outreach email should be to start a conversation, not make a sale. Build the relationship with the person first. If they are interested they will ask for more information or agree to a call. Remember, you're approaching a stranger. Don't freak them out by trying to "seal the deal" on the first email. Notice that nowhere on the list is “offer them a discount”. Why? Because you can’t discount a problem that they don’t believe they have. Think of cold outreach as a series of small bets. What’s the best way to know if your bet is going to pay off? Learn how to read the market. Great sellers have the ability to see patterns where no one else can. Reaching out to the right people, in the right way, at the right time, with the right message. Make this your obsession.

In almost every company I’ve worked at, I’ve built sales sequences for myself and teammates across all sorts of audiences. There are a number of ways you can improve the quality of your sequences without needing new costly tools. One way is messaging. What you use in your calls, emails, and DMs can make a difference, but it’s not a sure thing. You need real variety, or the contact will end up in the cold outreach graveyard where so many have drifted. ★ But another element you can easily control is the spacing and timing of your prospects. It’s a wildly overlooked area of sales sequence success. When you’re adding 100+ new prospects in a week to a cadence, it instantly turns into a numbers game because you can’t realistically get to everyone. It's chaos. And then reps get busy and skip critical manual tasks like cold calling or personalized emails. Or even worse, prioritize contacts with high opens and intent like they are Billy Beane in 'Moneyball' instead of the VIP target, who is almost always the buyer. ★ All this sales madness can be stopped though just by using throttling and adding 6 or fewer new prospects a day for AEs or 11 for SDRs. Spacing just makes it way easier for anyone to fit their sales to-dos into their schedule - all the flavors. And the more attention you can give each contact in your sequence, the better the chances you have of success. I recommend even taking days off so you can time up prospects for important tasks with days you know you can actually be locked into prospecting. But when you’ve got a ton of open manual tasks, no thanks. Easy skip. Cadence overload gives me sales anxiety just thinking about it. #prospecting #outbound #salestips

Deadlines drive deals. Without them, sales stall, and opportunities wither. Want to supercharge your sales cycle? Here's how: Communicate, don't assume. Need an estimate? Alert your estimator—give them a clear, reasonable deadline. It's not nagging. It’s navigating projects with professional urgency. It’s about precision and expectation. Tell them: "I need this for a client presentation. Can we have it by the end of Thursday?" Set boundaries and create accountability. Getting a signature? Specificity seals deals. Don’t leave meetings with a "Let's touch base soon." Instead, ask: “Can we lock this in by Friday? I want to ensure we hit your timeline for service.” Deadlines create momentum and demonstrate seriousness. Not imposed, but agreed upon. This isn't pressure. A partnership in urgency creates mutual wins. In sales, time kills deals. Deadlines keep them alive. Set them. Respect them. Close more. 

If you're getting nowhere prospecting right now, here's the 3 things you need to check to get the pipeline growing again: --- 1) List building is more important in a bad economy than messaging. Stick with me. Going wider when companies aren't buying doesn't give you better odds. This is the time to revisit your ideal customer profile and get ruthless building high quality, smaller lists. Yes it'll take more time, but the results are exponentially better when you focus on a particular segment within a particular industry with a particular problem then blasting every company with X00 employees. --- 2) State the negativity in your messages. It deflates it. How? Like this: "When things get rough with layoffs and slow downs nobody is eager to stick their neck out and call for organizational transformation. But I'd imagine your exec team still expects strong performance and is looking to see who will be clever working with less. Are you opposed to exploring ways to improve the process without needing to battle internally?" Take away people's obvious objections to buying things right now by just stating them. A seller can never lower their status with a buyer by being informed. --- 3) Fortune is in the follow up when you're prospecting. The best, most abundant meetings come from the companies you were prospecting months ago that asked you to follow up. Why? Because you're almost guaranteed to have the timing be wrong when you outbound. So lead with that and start collecting amazing follow up leads. Tell prospects "I'd imagine my unexpected message in February did not catch you at the right time when this problem becomes a priority. But that doesn't mean it's not a problem all the same. At what time of year does this become more relevant? When I follow up with you then, what do I need to include in the message to get your attention at that time? And is there anyone else that's going to prioritize this problem then as well?" --- Now we're cooking. Better lists. Clearer messaging. Nailing down the timing. Don't prospect like a maniac. Be ruthless with your time. --- Ready to conquer cold calling anxiety and start meaningful conversations with your buyers? Join +5,500 sellers using the Mic Drop Method, an easy to learn framework for starting dialogue with skeptical prospects: learntosell.io

Outbound Prospecting: Relevance > Personalization I'm much more likely to respond to a cold sales email if it's relevant to the challenges I'm currently facing, than if it's just personalized with my name, role, etc. What about you? 🤔 If it can be relevant AND personalized, that's even better, but this is time consuming for reps. So how do we get relevance at scale? One way is 𝘀𝗮𝗹𝗲𝘀 𝘁𝗿𝗶𝗴𝗴𝗲𝗿𝘀. Sales triggers are events or situations involving your target account that signal a potential need for your offering. They're your relevant reason to reach out. Here's how to use them: - Identify your ICP's triggers - Setup trigger tracking tools - Create message templates for each trigger To get the more detailed step-by-step process (as well as the different types of triggers and their messaging strategies), check out yesterday's 📰 𝗥𝗲𝘃𝗢𝗽𝘀 𝗪𝗲𝗲𝗸𝗹𝘆 📰 featuring sales trainer John Barrows Link to read on-demand in the comments below. 👇 ✌️

150 million job listings signals. 8 million news and events signals. Spanning 40 million companies around the globe. Refreshed daily. ☝️That’s what our latest product launch puts at your sales teams’ fingertips. Our customers tell us timing in sales is everything: Finding a high-fit account is good. Finding a high-fit, *high-need* account at just the right time? That’s orders of magnitude better. Common Room lets reps get scientific about great timing. Knowing what your prospects’ priorities are based on news and hiring signals makes it so much easier to: - Prioritize which accounts to go after - Zero in on the right person to outbound - Craft personalized, relevant messaging - Reach out at exactly the right time And this customer intelligence is available out of the box today on every plan. Here’s some real world examples of automated alerts and outbound workflows leveraging the science of great timing: - Hiring for desired skills (e.g., a job description that mentions “LLM prompt writing”) - Hiring for important tech (e.g., looking for experience implementing a “work management tool”) - Strategic priorities (e.g., an interview with a CxO that mentions “digital transformation”) - Urgent needs (e.g., a news feature about a recent security breach) - Financial health (e.g., an announcement about raising a series B) - Market challenges (e.g., just went through a round of layoffs) And that’s just the start! Our engineering velocity is simply unmatched right now🔥, so get ready for many more updates in the weeks ahead. In the meantime, check out the blog post in the comments to see how you can automate and scale deep buyer context and great timing ⬇️