Best Practices for Contact-Based Sales Outreach

What makes a decision-maker actually reply to your LinkedIn message? I wanted to find out. So we ran an experiment. At my recent Get Paid To Speak Bootcamp, I invited Brian Tee, Head of Sales at SingPost, as one of our corporate guests. Why? Because I wanted my aspiring speakers to hear directly from someone who hires speakers: what gets their attention, what turns them off, and what actually gets you booked. So here’s what we did: Everyone in the room had to reach out to Brian on LinkedIn. No scripts. No templates. Just thoughtful outreach. Brian received 95 connection requests and he took the time to go through every single one. Then he shortlisted the messages that stood out to him and shared WHY they worked. That’s what this post is about (you might want to bookmark this post!) Here are five things the best outreach messages had in common: 1. They anchored to a real, shared moment. “I really appreciated your insight at GPTS, especially when you said ‘leadership today requires empathy and adaptability.’ That stayed with me.” 2. They focused on Brian first not their pitch. “May I ask what business challenges you're currently facing? How do you envision inspiring your sales team in 2025 and beyond?” 3. They asked meaningful, open-ended questions. “What’s your take on vulnerability in the workplace? Does it have a place in leadership today?” 4. They aligned their offer with Brian’s values and goals. “Given your focus on transformation, I believe my talk on resilience could complement your vision at SingPost.” 5. They offered to add value without sounding transactional. “If there’s any way I could contribute to your work at SingPost, I’d be happy to explore how.” One big lesson from this? The best outreach doesn’t try to impress, it tries to connect. Respect. Curiosity. Relevance. That’s what opens doors. A huge thank you to Brian Tee for being so generous with his feedback, this was GOLD for every speaker in the room. And now, for you reading this: If you’re trying to reach high-value contacts, use the above five insights as your blueprint. Your turn: if you were a potential client, how should we reach out to you that will elicit a positive response? #LinkedInTips #GetPaidToSpeak

You spend 20 minutes researching someone, write a personalized message, hit send, and get blocked. That's not bad luck. You triggered something in the first three lines without realizing it. Here's what actually happened: Your message felt low-intent. Even though you researched them, even though you used their name, even though you mentioned their company, something in how you structured it made them think: "This was sent to 500 people." And when someone feels like target #247, they don't just ignore you. They block you. Here's the S.E.E.D framework we use to book calls without getting blocked: 1. Situational context-  ⤷ Start by showing you understand something happening in their world right now. ⤷ A market shift. A new hire. A product update.  ⤷ Not a compliment, a signal that says "I noticed." 2. Evidence of insight  ⤷ Drop one thought that proves you understand their landscape.  ⤷ "Usually when companies ship X, Y bottleneck shows up next."  ⤷ Insight is the new personalization. 3. Earned Permission  ⤷ Don't ask for a call. Ask for a micro yes.  ⤷ "Want the breakdown?" "Should I send it here?"  ⤷ Make it easier to say yes than to ignore. 4. Directional CTA ⤷ Your CTA shouldn't demand time; it should direct momentum.  ⤷Let them pull the conversation forward, don't push it. Outreach doesn't fail because people hate messages. It fails because people hate being treated like targets. When your message reflects thought, timing, and relevance, people don't block you. They engage with you. PS: Have you ever been blocked after sending what felt like a thoughtful message? #SalesTips #OutreachStrategy #ColdEmail #Personalization #SEEDFramework

Sales folks, take note! Spamming a target company's employees with your services and requests for meetings will result in your company making its way onto a buyer's blocklist. As a buyer in the localization industry, I receive dozens of emails and LinkedIn requests every single day from vendors looking to showcase translation, AI, QA services, and more. It's not humanly possible to give personal replies to every outreach. When vendors can't get through to me, they often reach out to everyone on my team... and sometimes to many others across my company. I'd love for this practice to stop. It wastes valuable company time and makes a vendor appear desperate and non-strategic. Here's what to do instead: 1. Appeal to ego! Invite a target company’s decision-maker to a panel, or start a vlog series and ask buyers to appear and discuss industry topics. It’s also a great opportunity to reposition your company as a thought leader. 2. Offer genuine insight, not just services. Share a case study, white paper, or benchmarking data that’s actually useful to the buyer’s role, and do it without a sales pitch. 3. Build a reputation before you build a pipeline. Comment thoughtfully on posts. Contribute to community conversations. If you consistently show up with value, you’re far more likely to get noticed. 4. Target smarter, not broader. Don’t shotgun your message to an entire company. Learn the org. Understand the buyer’s scope. Then send one well-researched, personalized note that shows you actually did your homework. 5. Focus on mutual value. Can you help solve a known pain point or offer perspective on something changing in the market? Frame your outreach around collaboration, not consumption. 6. Use timing to your advantage. Keep tabs on when companies are hiring for roles associated with your offerings, launching in new markets, or attending conferences. That’s when buyers are more receptive to new solutions. 7. Lead with generosity. Offer a no-strings-attached resource, intro, or suggestion that doesn’t benefit you directly. Reciprocity is a powerful trust builder. And please! Don't ever ever call me on the phone! ;)

I turned 10,000 dead CRM accounts into meetings using Clay workflows. The results were a 20% reply rate, over $200K in pipeline, and zero cold outreach. Most sales teams are sitting on a goldmine, yet they don't even know it. Here's how you can do the same: 1. TURN PAST CUSTOMERS INTO NEW OPPORTUNITIES Look for companies where your contract has ended or gone inactive. Import these accounts from your CRM into Clay. Find the original champion plus new decision-makers who've joined since. Then send targeted messages like: → "We worked with your sales team last year - wanted to share how we've solved the X challenge they mentioned" → "Since our last project with Acme Corp, we've added features specifically addressing your scaling issues." This approach feels like reconnecting, not cold outreach. 2. USE CHAMPIONS AS REFERENCE POINTS Find accounts where you had a strong champion in the past. Use Clay to verify if they still work there and in what capacity. Then reach out to new contacts in that account: → "Saw you work with Sarah, who implemented our solution for your marketing team last year." → "Your colleague Jason mentioned your team is facing challenges with X." Always verify employment status before sending these messages. 3. TARGET RENEWAL WINDOWS Pull contract end dates from your CRM into Clay. Create auto-updating lists that flag accounts 60-90 days before expiration. Find both original buyers and newly added stakeholders. Time your outreach perfectly by saying something like: → "Your current plan comes up for renewal in September - perfect timing to share what's new." This timing creates a natural sense of urgency without being pushy. 4. CONNECT THROUGH OFFICE LOCATION Import location data for your contacts from your CRM. Use Clay to find new prospects at the same physical office location. Verify if both your champion and new prospect work on-site. Write messages that reference the shared location: → "Noticed you work with Sarah in the Austin office - we helped her team last quarter with X" This creates immediate familiarity and leverages existing presence. 5. BUILD LOOKALIKE ACCOUNTS Take your best-performing customers from your CRM. Run them through Clay + Ocean.io to find similar accounts. Target these accounts with messaging that references success patterns: → "Companies like Apple, Tesla, and Spotify saw 43% faster sales cycles using our approach." → "Based on our work with similar X teams, we've found Y works well for them" This combines the credibility of social proof with personalization. _____ The real edge comes from maintaining good CRM hygiene and regularly updating data. Most teams are sitting on gold, but still use outdated or incomplete information. Start using what you already have instead of starting from scratch.

Most people think outreach is “DM 100 people and hope something happens.” That’s not outreach. That’s guessing. Real outreach is a system predictable, practical, and intentional. Here’s the process your competitors don’t follow: Step 1: Target the right people (not everyone) Your outreach fails because your list is random. Build a filtered list of: → People who already post → People who already buy → People already expressing the problem you solve Outreach works when your list is 80% pre-qualified. Step 2: Warm the lead before the DM This is where most skip. Before sending a single line, do this: → View their profile → Engage with 2–3 of their posts → Leave 1 genuine comment that adds value You’re in their notifications. You’re not a stranger anymore. This reduces resistance by 60%. Step 3: DM with context (not a pitch) Your first message should NEVER be your offer. It should be relevance + reason + recognition. Something like: “Been following your posts on X especially the part about Y. Curious, how are you currently handling Z?” This opens a conversation. Not a sales call. Step 4: Diagnose, don’t sell Your goal is to understand: → Their current situation → Their desired outcome → Their bottlenecks → Their timeline Your DM flow should feel like you're asking the questions they never thought to ask themselves. That’s how trust is built. Step 5: Transition to call without pressure Once they articulate the problem clearly, say: “If you want, I can walk you through exactly how to fix this on a quick call. No obligation.” This works because you're not pushing. You're offering clarity. Step 6: Follow-up sequence (the real magic) Most conversions happen in follow-ups, not the first message. Use a 6-day follow-up flow: → Day 1: Soft nudge → Day 3: Relevant insight → Day 5: Case study → Day 6: Invite to call again Not aggressive. Not annoying. Just consistent. Outreach works when done practically Not spammy. Not random. Not desperate. Outreach is simply starting conversations with the right people, in the right way, with the right timing.

Most sales outreach isn’t bad. It’s worse than bad. It’s invisible. Reps are blasting cold emails at scale, cranking out cookie cutter LinkedIn messages, and making calls that sound like they’re reading from a hostage script. And then they wonder why no one responds. Always keep the following in mind: Buyers don’t ignore you because they’re busy. They ignore you because you’re forgettable. If you want to separate yourself from the noise, stop making noise and start making impact. Here’s how: 1. Cut your target list in half...then cut it again. Narrow your focus to the most qualified, highest value prospects. You don’t need more at-bats. You need better at-bats. 2. Personalization > Personalization Tokens - “Hey {First Name}, I saw {Someone} left you a recommendation” isn’t personalization. It’s AI-generated small talk. Connect the dots between their world and your value. 3. Lead with insight, not inquiry - “Can I get 20 minutes?” isn't a good closer. Give them a reason to want the conversation before you ask for it. 4. Become a student of your buyer’s business - If your email could be sent to any random company in their industry, you’ve already lost. Show you’ve done your homework. 5. Play the long game - The goal of outbound isn’t just meetings. It’s credibility. It’s differentiation. It’s making them remember you when the timing is right. Lazy outreach is just noise. Thoughtful outreach is leverage. Outreach isn’t a numbers game. It’s a value game. If you want to separate yourself from the noise, stop making noise and start making impact.

After 220+ closed deals, here’s one thing I’ve learned: One channel isn’t enough anymore. In 2025, prospects live everywhere - and if you’re only emailing or only calling, you’re invisible. Here’s exactly how to build a multichannel approach that actually works: 𝟭. 𝗦𝘁𝗮𝗿𝘁 𝘄𝗶𝘁𝗵 𝘀𝗶𝗴𝗻𝗮𝗹, 𝗻𝗼𝘁 𝘀𝗽𝗿𝗮𝘆 → Don’t start by sending 100 messages. → Start by finding why to reach out. → Use intent tools, job changes, or hiring spikes to time your outreach. 𝗔𝗰𝘁𝗶𝗼𝗻: Make a “trigger list” - 3 reasons someone might care today, not someday. 𝟮. 𝗪𝗮𝗿𝗺 𝘁𝗵𝗲𝗺 𝘂𝗽 𝗯𝗲𝗳𝗼𝗿𝗲 𝘁𝗵𝗲 𝗰𝗮𝗹𝗹 → Comment on their posts. → React to company updates. → Send a relevant note or insight before you ever call. 𝗔𝗰𝘁𝗶𝗼𝗻: Block 10 minutes daily for “pre-touch” activity on LinkedIn. 𝟯. 𝗖𝗼𝗺𝗯𝗶𝗻𝗲 𝘆𝗼𝘂𝗿 𝘁𝗼𝘂𝗰𝗵𝗲𝘀 𝗶𝗻𝘁𝗲𝗻𝘁𝗶𝗼𝗻𝗮𝗹𝗹𝘆 → Day 1: Personalized email → Day 2: Call → Day 4: LinkedIn message → Day 6: Follow-up with new angle → Day 10: Pattern interrupt (voice note, short video, or DM) 𝗔𝗰𝘁𝗶𝗼𝗻: Create a 10-day cadence that mixes all three — and stick to it. 𝟰. 𝗠𝗮𝗸𝗲 𝗲𝗮𝗰𝗵 𝗰𝗵𝗮𝗻𝗻𝗲𝗹 𝗱𝗼 𝗮 𝗱𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁 𝗷𝗼𝗯 → Email = insight → Call = connection → LinkedIn = credibility → Video = emotion 𝗔𝗰𝘁𝗶𝗼𝗻: Stop copying the same message across channels. Align tone to medium. 𝟱. 𝗨𝘀𝗲 𝘁𝗲𝗰𝗵 𝘁𝗼 𝘀𝗰𝗮𝗹𝗲, 𝗻𝗼𝘁 𝘀𝗽𝗮𝗺 → Tools like ️Salesforge 🔥 make this easier in 2025 enroll contacts, sequence across channels, and scale what’s working. 𝗔𝗰𝘁𝗶𝗼𝗻: Spend one hour a week reviewing data. If a channel underperforms, tweak your message, not just your volume. The result: - 3x reply rates - More live conversations - Stronger pipeline consistency My take: Multichannel isn’t about doing more. It’s about doing the right thing in more places. Your prospects don’t live in one inbox - so your outreach shouldn’t either. PS. Curious - are you a phone, email or LinkedIn person?

Ever wonder what makes a prospect actually respond to cold outreach? Let me share a recent experience that breaks down the art of engagement from both the prospect's and the sales rep's perspectives. Prospect's Perspective: Emily Leu shared the following insight about cold outreach that led to a meeting: “I recently connected with a BDR from Lavender 💜 after meeting someone (maybe an AE?) at an event. I might have gotten myself tagged as an MQL! 😅 Here’s how the outreach played out: Hyper-Personalized Email: The email felt customized—even if it followed a framework, it clearly wasn’t a mass template. Quick Follow-Up: I missed the email, but a LinkedIn connection request with a personal note nudged me to check my inbox again. Non-Committal Response: I replied on LinkedIn, but life got busy, and I forgot about it, even though I was interested. Text with a Voice Note: A few days later, I received a text with a voice memo. What worked? The combination of hyper-personalization, brevity, and a multi-channel approach that built upon previous touches. It was relevant and easy to digest!” --- Sales Rep's Perspective: Nihal D., the Sales Jedi who concocted this outreach, shared the following perspective: “Shoutout to 💜 Will Allred, who taught me a lot about effective outreach. One key takeaway: there's a crucial difference between relevant outreach and mere personalization. While personalization might be a casual nod (like, "Saw we both went to ABC school. Go Alphabets!"), relevant outreach digs deeper: "With your Series B a couple of years ago and your team ramping up AE hirings, am I right in thinking you're prepping for another round? Key Strategies: Digestibility is Key: I focus on proper spacing, low word count, soft CTAs, and mobile-friendly content. The easier it is to read, the better! Multiple Channels: If I don’t get a response after my first email, I reach out on LinkedIn to open another channel—just a friendly nudge to chat. Embrace Unconventional Methods: My final touch? A text with a voice memo! While sending a text might be controversial, it’s effective. Everyone checks their phones, and voice memos have a higher engagement rate than traditional voicemails. Plus, I can re-record as many times as needed! “My goal? To stay top-of-mind for at least 48 hours. If anything I shared resonates, the prospect will think it over and hopefully reach back out.” --- 💡 The takeaway? Cold outreach isn't just about being seen; it's about creating a thoughtful, engaging experience that makes prospects want to connect. Happy prospecting!!! P.S. DM me if you have a recent example of cold outreach that led to a meeting!

The days of "I noticed you like Guinness!" personalization are dead. Here's how top sales teams are identifying specific pain points their solution can uniquely solve. After building Apollo's AI research agent from zero to thousands of users, I've seen what separates good prospecting from great - and it's not what most people think. The Old Way: Generic Filters & Surface-Level Personalization - Start with basic filters: job titles, industry, company size - Download list, manually research each prospect - Find something generic to mention ("saw you went to Stanford!") - Send bland outreach with superficial personalization - Hope for 1-2% response rates while burning through your TAM The New Way: AI-Powered Pain Point Identification 1. Multi-source data enrichment: Configure multiple data sources in one place to maximize contact accuracy. For example, set up a waterfall enrichment that tries several email and phone providers in sequence to find valid contact information before your first touchpoint. This significantly increases your reach rate without wasting time on bounces. 2. AI qualification for genuine pain points: Create natural language prompts that identify prospects with problems you can solve. For a localization company, this means scanning websites for translation gaps. One prospect had a product supporting 30+ languages but maintained an English-only website – a perfect opportunity to start a value-driven conversation about expanding their web presence. 3. Signal stacking for personalized outreach: Combine multiple signals in priority order to craft messages that address specific pain points. Look for companies showing international expansion signals alongside their existing language limitations. One prospect was expanding overseas but only offered English language support – a clear opportunity to help them scale localization for customer acquisition in new markets. The result? Instead of "Hope this email finds you well," you can send: "We noticed you support 14+ languages in your product, but your website is only in English. Are you looking to expand your website to better service your international users?" The best part? You can do all of this inside Apollo.io - from initial prospect search to multi-source enrichment to AI custom research to signal stacking to AI messaging - in just a few clicks. Check out the demo to see how easily you can transform your outreach from generic to genuinely valuable.

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.