Prospecting Strategies

Outbound is dead in cyber. Long live AE-owned prospecting. I will die on the hill of "outbound is dead". But it's been misunderstood when I've brought it up here. In cybersecurity, generic mass outreach is dying or it's a zombie waiting to be whacked. Targeted, value-driven prospecting led by Account Executives is thriving. SDR's have a hard time doing this not because they can't, but because the system is not setup for them to do it (i.e. comp plans, org structures, etc.) We know from research that personalized outreach based on deep account knowledge delivers 3x better engagement than templated SDR approaches. Yet we keep trying to build outbound motions with higher volume and worse conversion rates 🤮 Here's my framework for building a repeatable pipeline development program where AEs actually own the process: 👉 *The Value Hypothesis Approach* 1. Narrow the focus dramatically: Your target account list should be small enough that each account gets hours of dedicated research. 2. Make AEs accountable for contact mapping They need to identify key stakeholders and understand the organizational dynamics before any outreach begins. 3. Develop specific value hypotheses This is the game-changer. Each account gets 2 customized value proposition based on their specific situation. 4. Collaborate on hypothesis refinement The best teams involve SE/PreSales, Product Management, and Sales Leadership in critiquing and improving these hypotheses. 5. Execute with precision With this foundation, outreach becomes a targeted conversation rather than a generic pitch. 6. Close the feedback loop: Sales leaders need to document which value hypotheses resonated and which fell flat - this becomes your competitive advantage. The best-performing enterprise sales teams allocate at least 1/3 of AE time to this process. Yes, it's resource-intensive, but the results speak for themselves. 2 hours a day (minimum) every day, every AE, for 3 months. Then come back and tell me 'thank you' Unexpected benefit: When AEs spend 10+ hours weekly on strategic prospecting, your inbound and partner-led conversion rates automatically improve. Why? No AE will let warm leads slip after experiencing how much work cold prospecting takes. Pro-tip? Spend 'Training Thursdays' evaluating value hypothesis together. Double pro-tip, combine Value Hypotheiss with 'Show me You Know Me' on your messaging (follow Samantha McKenna - She crushes SMYKM content) Anyone here that calls value hypothesis something else? I used to call it my 'angle'. Need something more catchy and less scientific-sounding 😆

Reps who are great at prospecting aren't focused on pitching—they are focused on connecting. Too many salespeople treat prospecting like a game of darts in the dark, hoping something sticks. But hope isn’t a strategy. If you want real results, you need to shift your mindset and your approach. 1. Be Relevant, Not Random Your prospects don’t care about your product—they care about their problems. Do your homework. Research your prospect’s industry, company, and specific pain points. Then craft a message that speaks directly to them. If your outreach feels generic, it’s already in the trash. 2. Lead with Value, Not Features Nobody wakes up thinking, “I need a new software solution today!” They wake up thinking about how to hit their goals, fix bottlenecks, and grow their business. Your outreach should answer one question: “What’s in it for them?” Educate, inspire, and provide insights before you ever ask for a meeting. 3. Keep It Short and Simple Your prospects are busy. If your email is a wall of text, they’ll move on. If your voicemail sounds like a dissertation, they won’t call back. Get to the point. One problem, one solution, one clear next step. 4. Follow Up Relentlessly (But Respectfully) Most sales happen after the fifth touchpoint, but most sales reps give up after three. Persistence is key, but so is tact. Mix up your approach—email, phone, LinkedIn, even a personalized video. And always add value in every follow-up. 5. Master the Art of the Conversation Scripts are a great starting point, but real connections happen when you listen more than you talk. Ask great questions. Be genuinely curious. Engage in a real dialogue instead of rushing to the pitch. Prospecting isn’t about selling—it’s about starting conversations that lead to relationships. Nail that, and the sales will follow. Now, go pick up the phone and make something happen!

AI has made executive prospecting almost unfair. Not because it replaces the seller. Because it compresses the research, relevance, and writing that used to take hours into minutes. I’ve carried a quota for 25 years. I’ve booked meetings the old way: Cold calls. Manual research. Long account plans. Guessing at the executive angle. Trying to write the perfect note from scratch. Now? I use Copilot, ChatGPT, LinkedIn, Sales Navigator, annual reports, websites, press releases, and executive posts to build a point of view faster than ever. The goal is not “send more emails.” The goal is send better ones. More specific. More mission-aligned. More executive-ready. More worthy of a reply. Here are 5 prompts I’ve actually used lately to book meetings: 1. Executive research “Analyze this executive’s company website, mission, annual report, recent press releases, and LinkedIn activity. Identify their likely top 5 priorities, the language they use, and the strongest reason they would take a meeting with me.” 2. Two-sentence hook “Based on this executive’s mission, LinkedIn tone, current initiatives, and likely priorities, write a 2-sentence outreach hook that is specific, value-focused, non-salesy, and strong enough to earn a reply from a C-level executive.” 3. High-probability email “Write a 2-paragraph email to this executive that maximizes my probability of earning a meeting. Use themes from their mission, website, annual report, and LinkedIn page. Make it short, executive-ready, value-focused, and include a subject line designed for open rate.” 4. Sales Navigator targeting “Based on this organization, my solution set, and the outcomes I can help drive, identify the highest-probability executive titles and functions to target in Sales Navigator. Include keywords, seniority levels, departments, and likely buying committee roles.” 5. Account strategy “Build me a meeting strategy for this account. Identify likely business problems, executive stakeholders, mission-aligned value, the best first message, the best follow-up, and the strongest reason they should meet now.” Those prompts power 80% of my prospecting motion. AI didn’t replace the craft. It amplified it. It made me sharper. Faster. More prepared. More relevant. Most sellers are using AI to write. The best sellers are using AI to think. That is the difference. Save this if you’re building your own AI prospecting system. What is one AI prompt or workflow that has genuinely changed how you sell? For my entire playbook, check out Moneyball Sales 📘 Paperback: https://lnkd.in/gHunVM8R 📱 Kindle: https://lnkd.in/g-3N52Hu 🎧 Audible: https://lnkd.in/gdY6nHkw All proceeds go to The Michael J. Fox Foundation for Parkinson's Research

Prospecting isn’t about chasing everyone—it’s about focusing on the right ones. Too many salespeople still believe that the more calls they make, the more demos they run, the more activity they generate… the better their results will be. But activity without qualification is just noise. And noise doesn’t build pipelines. The real differentiator in sales is your ability to quickly determine who actually has potential—and who is simply taking your time. It starts with identifying true buyer intent—not just interest. Then, understanding the problem they’re trying to solve, whether your solution is truly viable, and who the actual decision maker is. From there, you uncover the level of proof they need and how they personally define success. When you ask these questions early, you protect your time, increase your close rate, and build stronger relationships with customers who genuinely value what you deliver. Great prospecting isn’t about doing more. It’s about doing what matters. Focus on the right prospects, and everything else becomes easier.

Last week, I had the privilege of speaking to a few hundred young CRE brokers about how to get your business off the ground in the beginning of your career. Here's a snapshot of what I shared: 1) Prospecting in Today’s Market: Has it changed? Absolutely! There are more ways than ever to reach prospects. BUT, the cold call remains the most powerful tool to connect with owners. 2) Mindset Matters: Know your "Why." Do you have the resilience to handle the constant “No’s”? Do not get discouraged by all the rejection, there is a light at the end of the tunnel if you push through and don't quit. 3) Consistency: You will not feel 100% every day. Somedays you'll feel tired, sick, unmotivated, hungover, etc. Doesn't matter. Keep doing the work regardless of how you feel and eventually you will see results. 4) Preparation is Key: Start your day with a structured, repeatable routine. Craft hyper-specific interest generators, plan your calls, gather data, and role-play. 5) Execution Metrics: Track your numbers like your business depends on it (because it does). What’s your plan? How often do you review your stats? Every call should have a purpose and an attempt to close. 6) Fortune in the Follow Up: Consistently log your calls in a CRM (DO NOT USE EXCEL). Take detailed notes and never stop following up with prospects, even when it seems like a dead end. A "no" today can easily turn into a "yes" tomorrow, but only if you stay top of mind and maintain that connection. 7) Winning Prospecting Mediums: Post on social media DAILY and attend industry events at least quarterly. The more people that know who you are and what you do, the more successful your business will be. 8) Final Thought: Focus on one actionable step to boost your prospecting game and implement it immediately. You are the CEO of your business, so act like it and aim to get 1% better every day.

If I was a VP of Sales of a +$10M ARR company, and I had to generate $2M in new pipeline in the next 30 days to hit my growth targets, here are the only 4 plays I would have our AEs run: 1. Supercharge my Closed Lost process and focus on "revived" opps Over 90% of closed-lost opportunities sit untouched for 18+ months. Meanwhile, GTM teams obsess over cracking into new accounts. That means the highest-potential pipeline is in the deals you already worked. Most of those calls were recorded. And buried in them are signals like: - “Budget is frozen until Q2” - “We’re up for renewal with [Competitor] in 6 months” - “New CMO starts this summer” But no one follows up. If your closed-lost strategy is just running a report every quarter and pinging reps in Slack... you're leaving money on the table. 2. Track my champion movement and turn them into high-converting warm pipeline 52% of buyers say their previous experience with a product is the #1 factor in choosing a new vendor (TrustRadius). That means our former customers—people who loved our product—are now our warmest prospects. But most teams don’t actually track where those champions work today. Running the occasional Sales Nav search doesn't cut it. Instead, I’d run a dedicated enrichment project to map where our top advocates have landed. Then reach out with tailored offers—not our standard prospecting sequence. You’ll be shocked how many new opportunities are just one text, Slack DM, or warm intro away. 3. Mine our power users to unlock bottom-up pipeline The fastest-growing SaaS companies don’t start at the top. They win deals by starting with end users or middle managers—then earning their way up. Why? Because execs increasingly trust the tools their best people already use. I'd run a report of our top 20–40% most active users from the past 18 months. Then find out where those users work now. There’s a goldmine of warm pipeline waiting in those usage logs. You just have to dig. 4. Fix our CTAs — Make the offer actually worth their time If our AEs and BDRs are only offering a 30-minute meeting, they’re handicapping their efforts. Buyers are busy. Most don’t want another sales call. But they will engage—if the offer is valuable. So I’d swap the generic CTA for something specific, relevant, and hard to ignore. A great example: Brian Hamor at Buyer Experience offers a "win-back audit"—a compelling reason to engage that feels like a win, not a pitch. TAKEAWAY I don’t need more leads. I don’t need more accounts. I need to mine the ones I already have. There are millions of $$$ in pipeline trapped inside: - Our CRM - AE notes - Old calls - Past champions Our systems are full of real buying signals. But 99% of teams are too obsessed with net new accounts to go looking. Volume isn’t the answer anymore. The gold is buried in our own data. Start digging. Stop spamming. Use first-party signals. Win without the noise.

I targeted CFOs when selling my ERP services – and that was a big mistake My assumption was the following: these guys are signing the cheque and in charge of systems. I should go after them. The cold outreach on LinkedIn was a total disaster. I had less than 5% acceptance rate. But it was getting worse. Out of 100 accepted connections no one engaged in a conversation with me. Nada! So I went back to my friend nicholas thickett who is big on prospecting and asked for his advice. He taught me his mapping the earthquake approach. I was selling ERP implementation and support services to enterprise accounts going through SAP implementation. In the center of the earthquake we placed a persona who was experiencing the pain our solution solved. In my case these were systems analysts who were working on the implementation project and going to a support phase. SAP was new to them. It’s hard to learn. And they were worried about the future. In circle 2 were IT, ERP managers and directors. They cared about the outcomes of analysts’ work. Circle 3 were executives with signing authorities. Equipped with the new knowledge I started my prospecting journey again but now with a few changes. 1.     Outreach to systems analysts And here I had a big success. Much bigger acceptance rate. And also they were willing to engage in a conversation. And they told me a lot about what was going on with their systems and projects. 2.     Shift in focus I was not trying to sell to everybody. This time the goal was to discover if the account was qualified. 3.     Building the business case I gathered all the intel so that I could map the prospect’s pain to my cases and service. It’s also the time when I assessed the risks if something could derail the deal. 4.     Next step was to go up the ladder With internal referrals or cold but with precise message I connected with IT stakeholders. Since I knew so much about their situation, they were more willing to have a conversation. That’s where I identified the champion who helped push through the solution with all the involved parties. It went much easier this time. I was able to close a client that I worked with for the next 18 months. That’s it. Don’t chaise C-suite. They are already bombarded. Try users in trenches instead.

Harsh prospecting truth for fellow brokers: Random dialling RARELY ever works. Prospecting without a plan is just meaningless activity. My businesses success starts with a prospecting plan. I first isolate the exact properties in my market that match my expertise. For me, that is shopping centers and office buildings in 3 key areas. Next, I determine who is most likely to sell in the next 3–5 years. I use a handicapping system, I have developed over decades. It is based on prior conversations, ownership history, loan timing. Property performance, and how each owner makes decisions. I am very selective about which properties and owners I track. Every conversation is documented in my CRM with detailed notes. That allows me to pick up exactly where I left off months or even years later. I also spend time studying the market every single week. I read constantly and share relevant insights with owners. My calls are never random they are are purposeful. Because when you consistently bring value and stay present. You naturally become the first call when the time to sell arrives. That’s why it’s so important to prospect intentionally. #OnMondayImProspecitng

Last quarter I watched one of my top clients scramble to hit quota. He was the THIRD highest performer in his company (out of 10 reps). His activity levels were high. His close rate was even better. But something was VERY wrong... When we looked at his calendar, we discovered he only had THREE discovery calls the ENTIRE MONTH. The pipeline was a mirage. Here's the hard truth most sales leaders won't tell you: Activity ≠ Results Another rep I know made 14,000 calls in a month without booking a SINGLE meeting. Elite performers don't just work harder - they work DIFFERENTLY. 👇 THE ELITE PROSPECTING FRAMEWORK 👇 This is the exact system I've used to build a 7-figure sales career and coach hundreds of reps to double their pipeline in 30 days: 1️⃣ BLOCK YOUR CALENDAR RELIGIOUSLY Schedule 8 hours of dedicated prospecting time weekly (2 hours per day, Mon-Thu) Make these blocks SACRED - nothing overrides them Set them early (8-10am) when your energy is highest Put them as recurring meetings in your calendar NOW Label them clearly: "PROSPECTING - DO NOT BOOK" 2️⃣ RESEARCH BEFORE YOU REACH OUT Dedicate a separate full 2-hour block weekly just for research Validate contact data quality (bad data = wasted time) Identify true buying signals (not just basic triggers) Create a targeted list of 50 PERFECT prospects Document 2-3 personalization points for each target Use tools like LinkedIn, company news, and your CRM data 3️⃣ TARGET THE RIGHT ACCOUNTS Quality ALWAYS trumps quantity Focus on 50 perfect-fit accounts, not 500 random ones Build your list based on clear ideal customer criteria Segment your list by industry, pain point, or use case Prioritize accounts showing buying signals Remove any contact with questionable data quality 4️⃣ EXECUTE WITH PRECISION When you sit down to prospect, it's EXECUTION time only No researching, no planning, no "figuring it out" Follow your pre-built list in order of priority Mix methods: calls, emails, LinkedIn, video Track your results meticulously Adjust your approach weekly based on data 5️⃣ LEVERAGE YOUR SDRs Schedule weekly 15-minute alignment sessions Coach them on messaging that's working for you Give specific feedback on recent meetings they've booked Share your target account list with them Create a feedback loop on what's generating responses THE RESULTS SPEAK FOR THEMSELVES! My client implemented this system and went from 3 to 8 Enterprise discovery calls per month. That's 166% more pipeline. That's 166% more potential commission. That's the difference between missing quota and crushing it. The math is simple but brutal: If your prospecting is inconsistent, your results will be too. If your calendar doesn't protect prospecting time, it won't happen. If you're not tracking the right metrics, you can't improve them. Want to prospect better? Start with a great cold email: https://lnkd.in/gKSzmCda

The prospecting system that books 20-30 meetings/month 👇 Most reps wake up hoping for meetings The best reps wake up knowing they’ll get meetings Why? Because they work a system If you want at least one meeting a day or even a hat trick with three in a day you need to consistently hit these four outbound levers • Cold calling the fastest way to get live conversations • Email outreach the most scalable channel • Social selling where your prospects are already engaging • Warm intros & referrals the easiest “yes”    How to execute this daily? 👉 Cold calling (50-100 dials/day) • 15 dials before 9am = low resistance. fresh minds • Block 1-2 power hours during peak times (8-10am & 3-5pm) • Skip permission based openers. Get straight to it • Start strong "the reason for my call is..." then bring immediate relevancy • Use open ended questions to drive the convo forward    👉  Email outreach (25-50 emails/day) • Forget personalization. Relevancy wins every time • No fluff, no pitch slaps. Just get to the damn point • Imagine every word costs $1. Keep it under 70 words • Soft CTAs drive replies and move the needle      "worth a quick chat next week?"   "think this is worth exploring?"    • Follow ups win the battle. No “just checking in” BS • Every touchpoint should add value. Not just remind them you exist 👉  Social selling (25-50 connection requests + 10-15 DMs/day) • No pitch slapping have a damn conversation • Blank connect requests win no need for a note • Open a two way convo, seek to understand • Play the long game. Comment, add insights, make intros • Use video/voice notes (30-60 sec) to stand out 👉  Warm intros & referrals (5+ asks per week) • Happy customers? Ask for intros. "Who else in your network would find this useful?" • LinkedIn groups? Start convos. "Anyone here using [solution] for [problem]?" • Past prospects? Re engage. Deals that didn’t close but had interest So why does this all work? When done daily each lever creates opportunities across channels • One day an email reply turns into a meeting • The next a cold call gets a “yeah lets chat” • A well placed DM leads to “let’s book time” When all levers run consistently this system books 20-30 meetings/month Most reps think outbound is a guessing game It’s not. It’s a system Work the system and the system will work for you 👉 Whats your biggest struggle with prospecting?