[6] The 4 Rs of Prospecting, Jeniffer-Style
(Or how I learned to stop worrying and love cold outreach… mostly.)
When I played volleyball, I was a middle hitter. That meant two things: one, I had to be fast. Faster than the setter, faster than the block, and sometimes faster than my own decision-making. And two, I had to read the play before it happened. If I misjudged the ball, was slow to react, or went in with the wrong approach, I was either getting stuffed at the net or completely whiffing a perfectly good set.
Sales works the same way.
If you don’t have structure, you’ll waste time chasing the wrong plays—spamming contacts who don’t care, pitching to people with zero buying power, or missing the real pain point because you were too busy delivering a one-size-fits-all demo. But if you’re too rigid? You’re just another predictable player, easy to shut down. The magic is in knowing your system, adapting on the fly, and executing with precision.
That’s why I use the 4 Rs of Prospecting—Research, Relationship, Relevance, and Results. Think of it as my offensive strategy:
Research sets up the play. If I don’t know the gaps in their defense (pain points, buying triggers), I won’t score.
Relationship is the timing. Get it right, and I’m hitting clean. Get it wrong, and the ball sails out of bounds.
Relevance is reading the block. If I keep swinging in the same spot, I’m getting stuffed—so I adjust, tailor my approach, and find the open court.
Results are the scoreboard. If I’m not tracking what works, I’m just swinging blind.
When done right, prospecting isn’t just efficient—it’s personalized, high-impact, and almost effortless. Just like a well-executed quick set.
Let’s break it down.
1. Research: The Game Tape
Every great play starts with scouting. When I was playing volleyball, my coach never let us step onto the court without studying film. We analyzed our opponents’ weaknesses, tendencies, and even which setter had a tell before tipping the ball. Sales is no different—except instead of watching shaky high school sports footage, I’m deep in LinkedIn profiles, SEC filings, company reports, and blog posts, using every tool at my disposal to get an edge.
Know Your ICP: If you don’t know who your best-fit customers are, you’re setting yourself up for a lot of unnecessary blocks. I focus on industries that need compliance automation (think fintech, SaaS, and healthtech), then dig into pain points like audit fatigue, vendor risk, or (my personal favorite) “our last platform made us cry.” But this applies to any industry—whether you’re selling cybersecurity, logistics software, or coffee beans, understanding your ideal customer’s core problems is what makes your outreach land.
Use Every Tool in Your Arsenal: LinkedIn Sales Navigator, Apollo, company press releases, and even competitors' websites—if there’s data to be found, I’m finding it. Lately, I’ve been using ChatGPT to summarize SEC filings, earnings reports, and compliance updates to get a quick read on where a company’s security gaps might be. But the same approach works for anyone—if you sell to e-commerce brands, you could use AI tools to analyze Shopify trends. If you target manufacturing, pull insights from supply chain reports. I once uncovered a key pain point from a VP’s Reddit rant (truly, the internet never disappoints).
Industry Trends Matter: Just like knowing which volleyball rotations would throw off a specific team, staying ahead of industry trends makes outreach infinitely more effective. In my world, that means AI risk frameworks, SEC cyber regulations, or AWS security changes. But in another industry? It could be emerging marketing trends, supply chain disruptions, or new FDA regulations. AI tools help speed up the research, but the real win is turning insights into impact—showing prospects that I actually understand their world, not just copying and pasting stats from a report.
At the end of the day, research isn’t just about gathering data—it’s about arming yourself with the right information so you can show up prepared, personalize your outreach, and stay ahead of the competition. No matter what industry you’re selling into, the better you scout, the better you win.
2. Relationship: The Warm-Up
Last week, I talked about how horseback riding and sales have a lot in common—reading the situation, making quick adjustments, and, most importantly, building trust. Because if your horse doesn’t trust you? You’re getting thrown off before you even reach the first jump (been there, got the bruises).
The same goes for sales—you can’t expect a prospect to buy in if you haven’t built rapport first. If you come in too aggressive, too scripted, or without any real understanding of their world, they’ll buck you off the call faster than a spooked Thoroughbred. But if you build the relationship right, you’ll have them moving in stride with you, ready to jump the next hurdle together.
Engage Without Selling: I comment on LinkedIn posts, share relevant articles, and send funny but insightful emails. One time, I opened with “If compliance had a love language, it’d be automation”—got a reply within 10 minutes. Just like with horses, sometimes you have to approach from the side instead of head-on.
Personalization Wins: A cold, generic pitch is like trying to force a horse over a jump they’re not ready for—it’s just not going to happen. Instead, I tailor my outreach: “Saw you’re hiring for a security analyst—sounds like compliance is ramping up. Mind if I share how Secureframe automates half that workload?” performs about a million times better than “Hey, do you want a demo?”
Active Listening is a Cheat Code: In riding, you don’t just give commands—you listen to how your horse is responding. Sales is no different. People love to talk about their challenges, especially when they feel heard. When I was an SDR, I learned the hard way that launching into a product pitch before they finished venting was the fastest way to get ghosted. Now, I let them talk. The more they share, the better I can guide them toward the right solution—without forcing it.
At the end of the day, relationship-building in sales is just like good horsemanship—it’s about trust, patience, and knowing when to push forward versus when to hold back. Get that right, and you’re not just making the sale—you’re building a connection that lasts beyond just one deal.
3. Relevance: Connecting the Dots
If you haven’t read Dune (or at least seen the movie), here’s the short version: a desert planet, giant sandworms, political power struggles, and one guy—Paul Atreides—who figures out how to control the chaos and turn the tides in his favor. He doesn’t just charge in blindly; he studies the terrain, adapts to the conditions, and uses the right tools to survive.
Sales works the same way. If you’re not tailoring your pitch, you’re just another nameless Fremen wandering the desert, hoping to stumble onto success. The key is using the right strategy at the right time.
Tie the Product to Their Pain Points: If they’re struggling with vendor security assessments, I highlight Secureframe’s automated vendor risk management. If audits are the issue, I lean into our AI-driven test remediation. One size does not fit all—just like you wouldn’t survive Arrakis without adjusting your stillsuit.
Keep It Short & Sweet: If I can’t explain the value in two sentences, I know I’ve lost them. Rambling on in a pitch is like wandering the desert without a plan—eventually, the conversation dies of exposure.
Make It Feel Like Their Idea: The best sales conversations end with the prospect saying, “This is exactly what we need,” instead of me saying, “This is exactly what you need.” The most powerful ideas aren’t forced—they’re planted and nurtured until the person believes they’ve discovered them on their own.
Just like in Dune, sales is about strategy, adaptation, and knowing exactly when to strike. Get it right, and you’re not just closing deals—you’re shaping the future.
4. Results: The Scoreboard
At the end of the day, none of this matters if you’re not tracking success. I can send the best emails and have the greatest calls, but if they don’t convert? It’s just noise. And beyond just hitting quota, tracking success is about learning what works, what doesn’t, and how to improve. Because sales isn’t just about numbers—it’s about patterns, strategy, and constantly refining your approach.
Know Your Conversion Metrics (And Then Some): Of course, I track the basic – how many emails turn into meetings, how many meetings turn into proposals, and how many deals actually close. But the real insights come from digging deeper.
Which subject lines are getting the highest open rates?
Do prospects respond more to a certain CTA (e.g., “Let’s set up a quick chat” vs. “Here’s a case study”)?
What messaging gets them to engage beyond a surface-level reply?
When I was an SDR, I’d tweak subject lines like a mad scientist, A/B testing different approaches until I found the winning formula. Now, I look beyond just numbers—I track sentiment, responsiveness, and where deals stall in the pipeline.
Track the “Why” Behind Wins & Losses: Numbers tell part of the story, but the why is where the real gold is.
If I lose a deal, I don’t just mark it as “Closed-Lost.” I track why—pricing, timing, a competitor, internal bandwidth issues.
If I win a deal, I make sure I understand what tipped the scales—was it automation depth, pricing transparency, or our migration support?
If a prospect ghosts me, I look at when and where in the process they disengaged. Did I follow up too soon? Did they stall after seeing a case study?
By keeping tabs on these patterns, I can predict and prevent roadblocks before they happen.
Adjust the Playbook in Real-Time: Sales, like sports, is about adaptation. If I notice healthcare prospects engage more with compliance risk emails than automation ones, I shift my messaging. If a certain competitor keeps coming up, I fine-tune how I position Secureframe’s strengths to proactively address objections. Just like when I played volleyball—if the opposing middle blocker shut me down three times in a row, I wasn’t going to keep swinging in the same spot. I’d adjust my approach, change my timing, or start tipping the ball instead of powering through.
Measure Success Beyond Just Revenue: Not every win shows up in a dashboard. Some of the most valuable things I track don’t directly tie to revenue but make me better in the long run:
Time saved per deal cycle: If better messaging and automation cut my sales cycle by a week, that’s a huge win.
Quality of conversations: If I’m getting more in-depth questions and multi-threading earlier, I know my outreach is hitting the right pain points.
Brand recognition and referrals: Are prospects saying, “I’ve heard great things about Secureframe” more often? That’s a sign my presence in the market is growing.
Pipeline predictability: If my deal flow is steady rather than sporadic, I know my prospecting strategy is working long-term.
Keep Improving (Even When You’re Winning): Every lost deal teaches me something—how to pivot when a competitor comes up, when to push for urgency without being pushy, and when to let a deal breathe. But even wins can be optimized. If I close a deal in three months, I ask myself, Could I have done it in two? If a prospect goes from cold to closed-won in record time, I reverse-engineer what made that deal move faster.
Sales isn’t about perfection—it’s about iteration, improvement, and knowing that success isn’t just about hitting quota, but about getting better every single day.
Final Takeaway:
Whether it’s sports, sci-fi, or sales, structure matters. The 4 Rs help me navigate prospecting without feeling like a mindless cold-call robot. Research sets me up for success, relationships build trust, relevance seals the deal, and results keep me improving.
And if all else fails? I take a break, watch The Great British Baking Show, and remind myself that even the best bakers burn a few cakes.
Now, I want to hear from you! What’s your version of the 4 Rs? Do you have your own system for keeping prospecting structured but personal? Drop a comment below—I’d love to swap strategies.