Crafting Your 2H Big Deal Roadmap: A Summer Planning Guide

As the summer heat settles in, it's time to turn up the heat on your sales strategy. For big deal hunters, these quieter weeks offer the perfect opportunity to craft a winning game plan for the rest of the year. Let's dive into creating an individual business plan that will set you up for success in landing those whale-sized deals. 🐳

Step 1: Take Stock of Your Current Position 📊

Before we look forward, we need to understand where we stand:

1. Review Your Pipeline: • List all current opportunities • Categorize by stage, size, and probability
   

2. Analyze Your Metrics: • Pipeline yield (closed won deals / total pipeline) • Win rates by deal size and type • Average sales cycle length
   

3. Assess Your Quota Position: • Quota achieved to date • Remaining quota for the year
   

Pro Tip: Don't just look at the numbers. Reflect on the stories behind your wins and losses. What patterns emerge?

Step 2: Model Your Path to Quota 🎯

Now, let's do some reverse engineering:

1. Calculate Deals Needed: Remaining Quota / Average Deal Size = Number of Deals Needed
   

2. Factor in Win Rate: Deals Needed / Win Rate = Opportunities Required
   

3. Consider Sales Cycle: How many of these opportunities can realistically close by year-end?

   
   

Example:

• Remaining Quota: $5M

• Average Deal Size: $500K

• Win Rate: 25%

• Sales Cycle: 4 monthsAs we reflect on the first half of 2023, many sales organizations are diving into loss reviews, trying to understand where deals went sideways. But here's a provocative thought: you're likely focusing on the wrong end of your sales funnel.
  

Win reviews, not loss analyses, are your ticket to sales excellence. Here's why:

1. Buyers Who Choose You Are Invested in Your Success

When a customer selects your solution, they've made a significant investment - not just financially, but in time, resources, and organizational change. They have a vested interest in seeing you succeed because your success directly impacts theirs. This alignment creates an environment where customers are more likely to provide detailed, actionable feedback.

2. The Vetting Process is the Same, Win or Lose

Buyers who ultimately choose you go through the same rigorous evaluation process as those who don't. The difference? Winners can provide insights into what tipped the scales in your favor. This information is invaluable for replicating success across your sales organization.

3. Loss Reviews Often Yield Superficial Insights

Let's face it: buyers who didn't choose you have little incentive to help you improve. Their feedback often boils down to price or a single feature, missing the nuanced decision-making process that led to their choice. Win reviews, on the other hand, can uncover the subtle factors that truly drive decisions.

4. AI-Powered Analysis Uncovers Hidden Patterns

Don't waste time with surveys or written feedback. The real gold lies in live interviews. Insist on recording these sessions and leveraging AI-powered analysis to uncover patterns and insights that humans might miss. This approach can reveal:

• Key phrases or concepts that resonated across multiple wins

• Emotional triggers that influenced decisions

• Patterns in the buying journey that led to success 5. Make Win Reviews a Cornerstone of Quarterly Business Reviews

To truly capitalize on the power of win reviews, make them a non-negotiable part of your quarterly business reviews. This ensures that insights are fresh, relevant, and immediately actionable.

6. Executive Involvement Signals Commitment
   

For your largest and most strategic wins, insist that the CEO and head of sales participate in the review process. This accomplishes two crucial objectives:

• It demonstrates gratitude and commitment to your most valuable customers

• It provides top leadership with unfiltered insights into what's driving success in the field
  

Implementing a Robust Win Review Process

1. Schedule win reviews within 30 days of closing the deal

2. Use a consistent interview framework to ensure comparability across reviews

3. Record all interviews and use AI-powered transcription and analysis tools

4. Create a centralized repository of insights accessible to sales, marketing, and product teams

5. Develop a regular cadence for sharing key learnings across the organization

6. Use insights to continually refine your ideal customer profile, messaging, and sales process

   
   

The Bottom Line

While loss reviews have their place, win reviews are the untapped goldmine in your sales process. They provide deeper, more actionable insights that can dramatically improve your win rates and customer satisfaction.

As you reflect on your first-half performance, don't just focus on what went wrong. Dive deep into what went right, and you'll uncover the keys to replicating and scaling your success in the second half of the year and beyond.

Ready to revolutionize your approach to sales analysis? Let's talk. As an expert in sales strategy and win review processes, I can help you implement a system that turns every win into a blueprint for future success.

#SalesStrategy #WinReviews #RevenueGrowth #SalesLeadership

Calculation: 10 deals needed → 40 opportunities required → 20 can realistically close this year

Step 3: Identify Your Performance Levers 🎚️

To hit your target, you'll need to pull one or more of these levers:

1. Sell Bigger 🐘 • Upsell/cross-sell to existing customers • Focus on enterprise-wide solutions • Identify multi-year contract opportunities
   

2. Sell Faster ⚡ • Streamline your sales process • Improve stakeholder mapping and engagement • Leverage sales enablement tools more effectively
   

3. Win More 🏆 • Enhance your discovery and solution positioning skills • Improve your competitive differentiation • Strengthen your negotiation and closing techniques
   

Step 4: Tap into Hidden Goldmines 💎

Don't overlook these potential sources of big deals:

1. Current Customers: • Identify expansion opportunities • Look for new problems you can solve
   

2. Past Customers: • Re-engage with companies who've previously bought from you • Highlight new solutions or improvements since their last purchase
   

3. Dormant Opportunities: • Revisit deals that stalled but never officially closed • Approach with fresh insights or new value propositions
   

Step 5: Craft Your 2H Big Deal Battle Plan 🗺️

Now, let's put it all together into a concrete action plan:

1. Set Clear Targets: • Number of new opportunities to create • Pipeline value to build • Deals to close (by size/type)
   

2. Define Weekly Activities: • Outreach calls/emails to make • Discovery meetings to conduct • Proposals to deliver
   

3. Identify Key Accounts: • List your top 10 target accounts for big deals • Develop account-specific strategies for each
   

4. Plan Your Skill Development: • Choose 1-2 key skills to focus on (e.g., executive-level discovery, negotiation) • Set aside dedicated time each week for improvement
   

5. Leverage Your Network: • List 20 key connections who could introduce you to big deal opportunities • Plan how and when you'll engage them
   

6. Create Accountability: • Share your plan with your manager or a peer • Schedule weekly check-ins to review progress

   
   

Sample 2H Big Deal Battle Plan:

Week of July 10-14:

• Create 5 new opportunities (2 from existing customers, 3 new logos)

• Conduct 3 discovery calls with C-level executives

• Deliver 1 enterprise-level proposal

• Spend 2 hours improving executive presentation skills

• Reach out to 5 network connections for introductions
  

Key Targets:

• Pipeline Value to Build: $10M

• Deals to Close: 3 deals at $1M+, 5 deals at $500K-$1M

• Skills to Develop: Executive-level discovery, Enterprise solution architecture

  
  

Top 3 Target Accounts:

1. MegaCorp Industries

2. Global Innovations Inc.

3. NextGen Enterprises
   

Network Connections to Leverage:

1. Sarah Johnson - Former client, now CIO at Target Account

2. Michael Chang - VC partner with portfolio companies needing our solution

3. Alexis Rodriguez - Industry influencer who can make warm introductions

Remember, this plan is your roadmap, not a straitjacket. Be prepared to adapt as new information and opportunities arise.

The Power of a Plan 💪

By creating this detailed roadmap, you're not leaving your success to chance. You're strategically positioning yourself to land those game-changing deals that will not only hit your quota but potentially blow it out of the water.

This level of planning and foresight is what separates the good from the great in the world of big deal hunting. It allows you to be proactive rather than reactive, to create opportunities rather than just wait for them to come to you.

A Challenge to You 🏆

I challenge you to take a day this week to craft your own 2H Big Deal Battle Plan. Share your key targets (without revealing confidential information, of course) in the comments below. Let's inspire each other to reach new heights in the second half of this year!

Remember, in the high-stakes arena of enterprise sales, fortune favors the prepared. Use this summer lull to set yourself up for a record-breaking close to the year.

If you're struggling with landing and growing those big enterprise deals, let's talk. I've helped many clients just like you overcome these challenges and take their sales performance to the next level. Feel free to directly message me, and we can schedule a time for a confidential discussion.

Thank you for being part of the Big Deal Hunting community. Your pursuit of excellence in enterprise sales inspires us all. 🏆

#SalesStrategy #BigDeals #EnterpriseDeals #SalesPlanning #B2BSales #QuotaAttainment #SummerProductivity