Sales Metrics and Coaching Strategies

After 20 years managing global sales teams—gov, edu, enterprise, consumer—I’ve seen the same patterns of failure repeat. Here are the usual suspects: 🕵️ Witness Protection Program -Always “mid-deal” at a new job. Big logos in the pipeline, zero conversions. 🏈 The Hail Mary -One giant deal, always a month away from closing. Nothing else in the funnel. 🤝 Everybody Knows So-and-So -Endless industry connections. Can’t close. Relationships ≠ revenue. 📉 “I Can’t Sell This” Syndrome -Blames product or marketing. Often a rep who can’t articulate value or ask the right questions. 📦 I’ve Got Something to Sell You -Always pitching. Never partnering. Clients feel sold to, not served. 🗣️ The Conversation Hog -Talks 90% of the time. Never hears what the customer actually needs. ✨ Holiday Inn Express Hero -Confident, charming, but skips process. Confidence ≠ competence. What works? Process. Metrics. Discipline. 🏁 Track the right metrics: -Calls/emails sent -Meetings set/held -Stage-to-stage conversion rates -Time in stage / deal velocity -Pipeline coverage ratio (3–5x quota) -Forecast accuracy -Win % by stage 📊 Build a real process: -Define clear sales stages with entry/exit criteria -Use a consistent qualification framework (BANT, MEDDIC, etc.) -Conduct weekly pipeline reviews -Post-mortem every lost deal -Coach based on data—not vibes 🎯 Winning sales teams don’t guess—they inspect. And yes, after all this time, “The Little Red Book of Selling” still delivers more timeless sales truth than most courses out there. Sales isn’t magic. It’s measurable. #SalesLeadership #B2BSales #SalesProcess #CRM #SalesMetrics #SalesExecution #LittleRedBookOfSelling #PipelineManagement #SalesEnablement

Just watched a sales leader lose 5 of his top reps after spending months perfecting a "winning" sales methodology that his team HATED. After 18 months of work, the CEO killed his career with six words: "Your team keeps missing their numbers." After analyzing 300+ sales teams and thousands of reps I've identified the exact leadership framework that separates 90%+ quota attainment from the industry average of 60%. The BIG missing piece that most sales leaders miss? Stop running meetings as status updates. And start treating them as PERFORMANCE ACCELERATION ENGINES. Here is the GOLDEN Leadership framework: GROWTH MINDSET: Start every meeting with these 3 strategic elements. → Team member shares industry insight or sales technique (creates learning culture) → Discuss application to current deals (makes learning actionable) → Rotate presenters weekly (builds leadership skills company-wide) This approach increased team knowledge retention by 72% across my client base. OPTIMIZATION SESSION: Have top performers demonstrate and teach these 4 specific skills. → Objection handling techniques (with exact language used) → Discovery questions that uncovered hidden needs → Email templates that generated 80%+ response rates → Closing language that accelerated decisions Use this exact script: "Jeff, you closed that impossible deal with [company]. Walk us through exactly how you handled their [specific objection] so the team can replicate it." LEADERBOARD ACCOUNTABILITY: Create what I call the "Performance Matrix" with columns for. → # of Booked Discovery Calls (activity metric) → New opportunities generated (pipeline metric) → Percentage to monthly target (results metric) → Weekly win or learning (growth metric) DATA & DEVELOPMENT: Each rep inputs and shares three critical elements. → KPIs for the week (leading indicators - 100% controllable) → Sales results (lagging indicators - what they actually sold) → Wins or learnings (development indicators) EXECUTION: Randomly select an AE to role play live. → Use a jar or spinning wheel to pick sales scenarios → Focus on objections, cold calls, or tough situations → Play the difficult prospect yourself → Provide immediate feedback and coaching This gets your team sharper before they jump into their day, and knowing they might be selected drives preparation. NEXT LEVEL MINDSET: End with motivation to conquer the week. → Short visionary speech or gratitude to the team → Positive reinforcement → Ensure they leave with the right mindset This is what they'll remember as they enter their next task or meeting. "REAL RESULTS from this framework: ✅ An IT services client increased sales by 37% in just 30 days ✅ Average rep retention improved from 18 months to 36+ months ✅ Team productivity increased 42% with the same headcount ✅ Top performers stopped taking recruiter calls Hey sales leaders… want a deep dive? Go here: https://lnkd.in/e2iZ7Rmv

In this episode of #TheScienceOfScaling podcast, I am joined by Jonathan Vassil, #CRO at Toast. Under his leadership, Toast experienced unprecedented growth, skyrocketing from $20M to $3B in revenue! The sales culture he cultivated was a significant factor in their success. Let's delve into the key ingredients of this culture that we discuss in this episode. (1) Sales team quota attainment is not the best indicator of the health of the team and its potential to scale because a small number of sellers could drive that attainment. The percentage of sellers making their quota each quarter is a better indicator. You want that number to be between 60% and 80%. Your quotas are likely too low if it is greater than 80%. If it is less than 60%, you will probably have a bad sales culture where reps expect to lose. Jonathan embedded this principle into the organization by aligning some of his front-line sales managers' compensation with the percentage of reps achieving quota (2) According to a study by the Corporate Executive Board, if a sales rep receives more than three hours of coaching a month, they beat their quota by 7% on average. If they receive less than two hours of coaching a month, they miss by 10%. And yet, when the researchers went back and analyzed how managers were spending their time, coaching was last. Jonathan implemented a continual coaching culture by meeting with his managers at the beginning of every month to inspect the coaching plan for each salesperson and assess the quantitative impact of past coaching plans on each rep's performance. (3) One common coaching pitfall is focusing too much on the bottom performers (C Group). Research shows that the best return on investment in coaching time is on the middle performance tier (B Group). However, this doesn't mean you should neglect the As or the Cs. The key is balance. The ideal allocation is 20% of coaching time for the As, 60% for the Bs, and 20% for the Cs. This balanced approach ensures that all team members receive the support they need to excel. (4) Most great sellers do not make great managers. However, sometimes great sellers think the only way to grow and get promoted is to move into management. Mitigate this pothole by setting up a way for salespeople who want to stay as individual contributors to grow. Implement a promotion path that allows sellers to achieve higher OTEs as they achieve various performance milestones, such as exceeding a certain number of sales or consistently meeting or exceeding their quotas or maintaining a certain level of NDR. Create a win-win by designing the OTE increase to increase the pay per revenue sold for the rep and increase unit economic efficiency for the company.  Check out the full episode here: https://lnk.to/TSOS!mr