Sales Success Methods

How to sell (without feeling salesy): First, understand the Ethical Wealth Formula: (Value First × Trust Building) × Authentic Positioning  ———————————————————  Frequency of Asks × Pressure Tactics This isn't abstract theory. It's practical math: • Increase the numerator: deliver more value, build more trust, position more authentically • Decrease the denominator: reduce frequency of asks, eliminate pressure tactics • Watch revenue soar while your integrity remains intact Ethical doesn't mean unprofitable. It means sustainable. Principle 1: Value-First Monetization The approach that generates $864,000 monthly without a single "hard sell": • Deliver so much value upfront that buying feels like the obvious next step • Create free content so good people say "If this is free, imagine what's paid" • Solve small problems for free, big transformational problems for a fee Give until it feels slightly uncomfortable. Then give a little more. Principle 2: Trust Through Consistency I've never missed weekly content in 3 years, through vacations, illnesses, market crashes. The trust-building machine that works while you sleep: • Show up reliably when competitors disappear during tough times • Do what you promise, when you promise it • Maintain quality across every touchpoint One founder implemented this and saw conversions increase 74% in 30 days, without changing offer or price. Trust isn't built in grand gestures. It's built in boring consistency, most won't maintain. Principle 3: Authentic Positioning The approach that helped me raise prices 300% while increasing sales: • Own your expertise unapologetically, confidence is not arrogance • Speak to specific problems you solve, not vague benefits you provide • Tell detailed stories of transformation instead of listing features You don't need to be perfect to sell effectively. You need to be authentic about how you help. Principle 4: Invitation Vs. Manipulation The ethical alternative to high-pressure tactics: • Invite people when they're ready, don't push when you're ready • Create genuine scarcity (limited capacity) not fake urgency (countdown timers) • Respect "no" as "not now" rather than objection to overcome My most profitable sales sequence has zero countdown timers, zero artificial scarcity, zero pressure. Ethical selling feels like extending help, not hunting prey. — Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. Want to improve your sales strategy? Join our community of 172,000+ subscribers today: https://lnkd.in/eTp4jain

For my first 16 years in tech sales, I averaged 240K/year W2 income. In my last 4 years, I averaged 720K/year. In order to triple my income, I had to change my sales approach entirely. Here's what I changed: I started using a new approach that I now call Yo-yo selling: 🪀 Yo-yo selling emphasizes starting at the executive level, conducting thorough discovery within the organization, and then returning to the executive with a tailored business case. Like holding a yo-yo, you are constantly in communication with the Executive Sponsor and updating them as you collect information and conduct deep discovery lower down in their organization. You are literally going up and down the organization, but always taking everything back to the Executive Sponsor to surface your findings along the way. Here's a breakdown of the framework: 🎯 𝐈𝐚𝐧 𝐊𝐨𝐧𝐢𝐚𝐤’𝐬 “𝐘𝐨-𝐘𝐨 𝐒𝐞𝐥𝐥𝐢𝐧𝐠” 𝐅𝐫𝐚𝐦𝐞𝐰𝐨𝐫𝐤 This strategy involves a three-step process: 1. Start at the Top (Executive Engagement) Initiate contact with a senior executive to understand their most pressing challenges, the reasons behind the need for change, and the consequences of inaction. If your solution aligns with their needs, secure their sponsorship for further discovery within their organization. To secure the Executive Meetings, it's essential to create a tailored POV (point of view) on where you think you may be able to help them based on your initial research of their highest level goals and priorities. Chat GPT has made this research a LOT faster now. 2. Conduct In-Depth Discovery (Middle Management) Engage with department heads and key stakeholders to uncover the day-to-day challenges they face. Focus on understanding their processes, pain points, and the implications of current inefficiencies. Gather direct quotes and insights to build a comprehensive view of the organization's needs. 3. Return to the Executive (Present Findings) Compile the insights gathered into an executive summary and business case. Present this to the executive sponsor, highlighting how your solution addresses the identified challenges. Tailor your demonstration to focus solely on relevant aspects that solve their specific problems. 🚀 Why It Works 1. Accelerates Sales Cycles: Engaging executives early ensures alignment and expedites decision-making. 2. Builds Credibility: Demonstrates a deep understanding of the organization's challenges and showcases a tailored solution. 3. Facilitates Internal Buy-In: By involving various stakeholders, you ensure that the solution meets the needs of all parties, increasing the likelihood of adoption. I'm pleased to share that that Yo-yo selling was recently awarded as a Top 15 Sales Tactic of All Time by 30 Minutes to President's Club, and I received a cool plaque for entering the 30MPC Hall of Fame. Since I have no chance of entering the Hall of Fame for my baseball or golf game, this is a nice consolation prize 😁

There’s an AE on my team that hits 200% of quota. Consistently. 🤯 Here’s her secret:  She asks the hard questions. 1. “You mentioned [date] as a goal. What’s driving that timeline, and is that date firm?” Verifies whether the timeline is real or aspirational. 2. "Based on what you’ve seen so far, is there anything that’s giving you pause about moving forward with us?” Invites honest feedback to surface objections early. One of my favorites. 3. “How does our solution compare to others you’re evaluating?” Tests competitive positioning and whether you're the frontrunner. 4.“Who else on your team needs to feel good about this before a decision is made?” Instead of just jotting down names and objections, she builds pages in Aligned to address concerns. That way, when new stakeholders join later, all the context is already waiting for them. 5. “If [insert key stakeholder] were here, what concerns would they raise?” Forces your champion to think on behalf of other decision makers. Great way to learn real objections. 6. “Have you ever purchased something like this before? What did that process look like internally?” Surfaces potential red tape or hidden decision criteria. 7. “What needs to happen between now and [target close date] for this to actually happen?” Pushes them to co create the buying journey and surface risk. 8. “When you picture this going live, what’s the ideal outcome for your team in the first 90 days?” Surfaces their definition of success. These questions do 3 things: – Build trust. – Surface the real decision process. – Give you everything to close/won the deal. 🎯 Bonus Tip: She doesn’t just ask the hard questions, she operationalizes them in Aligned. Here’s how… https://lnkd.in/gs7Gt5Rd That’s how you turn discovery into closed/won deals. - Mike G

I watched a company lose a $1.2M deal last quarter because they were still running MEDDPICC like it's 1996. They identified a Champion and an Economic Buyer. They documented Pain points. They were textbook perfect. The problem in 2025 is that no single Champion can get a deal done. Sales methodologies from the 90s weren't built for today's buying committees, consensus-driven decisions, and distributed authority. The modern sale requires a complete methodology upgrade. No more obsessing over a Champion. You need relationships with the entire team. No more chasing generic Pain points. You need Numerical Priorities linked to business outcomes. No more vague "Compelling Event". You need documented, financially-validated trigger points. No more hoping for Decision Criteria. You need to shape it with objective benchmarks. The best sellers still run a methodology, but it's evolved. They're identifying group priorities, mapping out competing initiatives, and anchoring everything in provable ROI. Try this on your next deal…instead of asking "What's keeping you up at night?" ask "What are the top 3 numerical priorities for your department this quarter?" Watch how quickly you can separate real deals from wishful thinking.

Cold Calling Is Dying. Here’s What’s Replacing It. The numbers don’t lie: • Cold call success rates have dropped to 2.3% in 2025, down from 4.8% last year (Cognism). • 72% of sales calls never reach a person, and it takes 8+ dials to connect with just one prospect. • Only 28% of reps still view cold calling as effective. Meanwhile, high-performing teams are doing something different. Research-Driven, Insight-Led Outreach Wins: • Reps who thoroughly research their prospects are 3x more likely to succeed (Clevenio). • Prospect-specific research can lift conversions by ~30%. • Insight-led outreach builds trust before a call is ever placed. Email and Social Are Outpacing Phone-First Approaches: • Personalized cold emails outperform generic ones by 32%; average reply rates are 8–9%. • 78% of social sellers outsell peers, and social-enabled teams hit quota 66% more often. Takeaway: 1. The call is no longer the first touchpoint. It’s the third or maybe the fourth; it’s only viable once you have demonstrable engagement via other channels. 2. Buyers start with research—so should you. Start with research. Deliver value. Leverage email and social. Then—and only then—call with context. You’re no longer the teacher like when you were knocking on doors. 3. This is how modern sales works. And this is how trust is built at scale. Welcome to the future, my friends. 🙌🏾 #NervousSystemsStrategist #SalesLeadership #ModernSelling #ColdCalling #SalesDevelopment #InsightSelling #SalesStrategy #SalesEnablement

“Why should we pick you over others?” Wrong answer: “We have X years of experience.” Right answer: “Here’s the ROI you’ll get.” Let me explain. Last year, a tech agency came to me. - Long sales cycles. - Endless price objections. - Pitches all about their process. Problem? Clients don’t care about your process. They care about their payoff. So, we flipped the script. Built a Customer ROI Canvas. Now, every conversation sounded like this: 1/ Investment Clarity - Total spend - Timeline to finish - Team effort needed 2/ Financial Returns - Direct revenue uplift - Cost savings - Time-to-value 3/ Strategic Returns - Competitive advantage - Future opportunities - Risk reduction 4/ Personal Returns - Career growth - Less stress/better life - Recognition inside the company Instead of pitching features, they walked prospects through the canvas. Results? ↳ Sales cycle: 9 weeks → 3 weeks ↳ Price objections? Gone. ↳ Deal size? Up by 35%. Prospect became internal champion. Lesson? The best sellers don’t push services. ↳ They make ROI so clear that clients close themselves. Your move? Build your Customer ROI Canvas. Watch your close rate climb. Found this valuable? ♻️ Repost to your network 🔔 Follow 𝗦𝘂𝗿𝗮𝗯𝗵𝗶 𝗦𝗵𝗲𝗻𝗼𝘆 for more. -- Want to become the Strategic CEO your business deserves? 𝗦𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘁𝗼 𝗖𝗘𝗢 𝗠𝗮𝘀𝘁𝗲𝗿𝘆 — my free weekly newsletter, trusted by 1,800+ self-funded founders. Every Thursday, I share sharp, actionable systems to grow your revenue, profit, and business valuation — the same ones I’ve used to start, scale, and exit 2 MM$ companies. 🎁 BONUS: Get my CEO’s Growth Playbook — 27 powerful cheatsheets, you can implement immediately. Click "𝗩𝗶𝗲𝘄 𝗺𝘆 𝗻𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿" above 👆 or scan the QR code below 👇

Last week I spoke to a CRO who's team hit 225% of quota in Q3 ($74M - 80% of which came from his enterprise team) and won two new logos from Fortune 100 companies. Here are the 8 strategies he implemented to help get them there: 1. Hired senior sellers and directors who know the complex sale and pay them aggressively. He bought years of experience instead of trying to figure out true enterprise selling on the fly. This led to more near term success with large enterprises. 2. Got his internal executives on board to play cameo roles in strategic parts of important sales cycles. 3. Attracted board of advisor members who are mega-connected in the industries his team sells to. Their role is 100% to open doors at the executive level. 4. Gave sellers controlled access to board of directors / board of advisors to coordinate executive introductions. 5. Created multiple paths to executive engagement: - Produced serious, data driven thought leadership content. (Ungated industry surveys and benchmark studies). This kind of thought leadership is how to “sell without selling” at the highest level. - Convinced his CEO to become prolific on LinkedIn and Twitter. To see this play in action, watch CEO’s like Jason M. Lemkin and Sam Jacobs as they speak to their audiences every day (multiple times a day). And for a masterclass in gaining a followership, follow the queen of mindshare, Arianna Huffington. - Sponsors quarterly executive roundtables (execs only, no sellers involved - they engage later) 6. Built out a high-quality internal Value Engineering team. Solid business cases built on customer-derived assumptions are the currency your champions need to get buy-in for big purchases. 7. Built a Key Account program which gives marquee accounts special access to resources and (some) influence on product roadmap. The more special your big accounts feel, the stickier the relationship and the more TAM you can earn across their organizations. 8. Implemented governance structures with large customers. A good governance structure is a series of pre-agreed meetings throughout the year at different levels in the organization to care for and feed the relationship. The CRO told me, “Having a governance structure in place saves my sellers from having to chase meetings all the time and brings customer executives to the table for more strategic conversations.” It is these strategies (and more) which I teach in the Mega Deal Secrets Masterclass. If you are a sales leader looking to build a leaner, more efficient ENT selling capability, DM me to discuss. #sales #enterprisesales

Want to sell to a CISO? Start with this. Selling to a CISO is not supposed to be easy. We carry the weight of protecting an entire organization while juggling risk, budgets, and board expectations. What makes a difference is when someone approaches with thoughtfulness. The best partners I have worked with came prepared. They understood the company, the landscape, and what actually mattered. They shared insights instead of a pitch, and they showed value whether or not a deal was on the table. They invested in trust and relationships, not just transactions. And the ones who really stood out built those connections in person, not just with me but with my directs too, who often drive the decision-making. The best salespeople are also good listeners. They talk less and listen more. They do not try to speak knowingly about breaches or risks where it is not their expertise. They respect that credibility is earned by listening, learning, and adding value in the right ways. On the flip side, it is easy to see through shortcuts. Fear-based selling does not work. Generic outreach does not land. Automated cold messages go straight to the ignore pile. If you do not put in the effort, you cannot expect effort from the other side. And if the relationship ends once the contract is signed, it was never a partnership to begin with. One more thing: founders and CEOs who show up personally, instead of leaving it all to their sales team, make an outsized impact. When leadership invests in relationships, it changes the dynamic completely. At the end of the day, CISOs are not just buyers. We are people. If you lead with thoughtfulness, listening, and genuine connection, you will stand out more than any flashy demo ever could. And if you get it right, you do not just win deals, you earn long-term partnerships. #ciso #cybersecurity #infosec #informationsecurity #sales

Stop asking discovery questions like - What's your budget? - What's your timeline? - Who's the decision maker? - What are your decision criteria? - Are you looking at other solutions? They make prospects feel interrogated. ↳ And add zero value throughout the sales process. Start asking discovery questions like • If we solved (insert problem), what would be the impact for you & your team? • What's an ambitious but attainable timeline for go-live? • Are we okay missing that date - and what would be the consequences if we do? • Who else needs to be involved to get this on the radar of the executive team? • What are must-haves vs. nice-to-haves for you when it comes to choosing a new solution? • Have you taken a look at what else is out there? 2 key takeaways: 1. Discovery is not an interview. ↳ It's a process of guiding the buyer in their decision process. 2. Buyer experience is a differentiator. ↳The more value you add during the sales cycle, the more deals you will close. What else would you add?👇

I have been a VCISO for more than 6.5 years. A big part of my job is carefully evaluating and purchasing solutions that meet my client's strategic needs. Based on my experience attending dozens of vendor sales meetings, here are 6 things to consider when selling to CISOs. 1. Most CISOs simply won’t purchase solutions they haven’t budgeted for. There are rare exceptions. This makes sales cycles fairly long. Sadly, a good portion of salespeople try to push one-off sales at the expense of strategic relationships. The reality when the CISO is faced with two almost identical solutions, they will most likely buy from someone they know, like and trust. Effective cyber salespeople play the long game, understand the budget cycles and actively listen. 2. Avoid disparaging competing products. Sounds obvious but I have been in too many meetings where sales people waste precious time dissing competitors instead of carefully understanding what the CISO needs. Most CISOs hail from technical backgrounds anyway, they won’t be swayed by negative talk. The industry is very small - I have seen salespeople join the same competitors they once disparaged. Negativity sucks energy and screams desperation. 3. Don’t try sidestep the CISO, especially if you know them personally. This means the sales rep directly targets the CEO or other business leader, under the assumption that the top boss will then order the CISO to purchase their “cure-all” solution. This manipulative tactic backfires quickly as the CEO simply forwards the same sales copy back to the CISO, whom they hired to make such decisions. Equally important, stick to the agenda and avoid name dropping. The CISO will buy your solution because it’s a good fit, not because your know the CFO or some board member. 4. I can’t express this simple point enough. Effective selling is about connecting with the CISOs burning pains. Stay alert and take cues. Don’t keep pushing a product feature that the CISO has clearly stated they don’t need. Don’t bore the CISO with vanilla slides talking about the latest threats. Leave that to round-tables and conferences. It’s likely that the CISO already know where your solution sits on the Gartner Quadrant. You might need to completely ditch your glossy slides let the CISO lead the conversation. Sometimes the CISO simply wants to see the product in action. Death by PowerPoint kills dialogue. 5. Sometimes you’re simply not a good fit - there is no place for your solution on the CISOs road-map. Humbly acknowledging that and walking away reinforces your credibility. It’s a small industry, your paths will likely cross again. 6. Fear mongering never works. You can't scare an experienced CISO into buying a strategic solution - that simply comes across as patronising.