I closed an eight-figure deal with Berkshire Hathaway Home Services at Salesforce and had multiple 7-figure W2 years using Yo-Yo Selling as my enterprise sales framework.
Yo-Yo Selling is a strategy I developed for selling large, complex enterprise deals where you:
- Develop a Point of View: Build credibility with senior executives by figuring out what the company cares about before you meet with the executive.
- Start At The Top: Present that POV to the senior executives to understand their vision and get them to sponsor deeper discovery.
- Drop Down: Meet with the business stakeholders to learn how that vision is (or isn’t) being executed.
- Bounce Back Up: Come back to the executive with a strategic, aligned business case.
At the enterprise and high mid-market level, deals often have multiple stakeholders and the only way to justify a 6-7 figure investment is by aligning with a strategic vision.
The best part: it works even if you’re up against inertia or executive disengagement.
Let’s break it down step-by-step.
Step 1: Develop a Point of View
Trust is everything with executives.
You might be able to meet with an executive once, but you’ll never get access to them a second time if you burn their trust by showing up unprepared.
Before you ever ask for a meeting with the C-Suite, do the homework:
- I use earnings calls, press releases, annual reports, and executive interviews to understand what the company cares about.
- I build a POV that links their goals to specific ways I can help based on their key priorities and problems from the research.
- I reach out to the Senior Executive to share my POV and make it clear that I’ve already done my research in my outreach.
When I started working with Berkshire Hathaway HomeServices, we actually got rejected by leadership when we pitched a point solution.
That’s SMB/Mid-Market-level selling.
Instead of walking away, I stepped back and asked: What does this company really need?
Across their earnings calls and executive interviews, I found their true goal was transforming the customer experience for their 50,000+ agents across 1,500 offices and I knew Salesforce was the only company that could support that scale of transformation.
Then I took that POV to re-engage the COO directly.
Step 2: Start At The Top
When you meet with the senior executive, lead with your POV to establish immediate credibility and trust and demonstrate that you are focused on helping them achieve their strategic goals (not whatever random problem your product solves).
When I met with the COO, I brought a bold point of view. Not a point solution, but a transformation roadmap and how it laddered into each part of their organization from my research. I knew that if they continued with a point solution, they wouldn’t be successful in scaling the transformation across 50,000+ agents.
After sharing my POV, I transition to executive discovery and focus on asking big-picture questions to validate if your POV is relevant or top of mind for them.
Here are a few types of executive level questions to ask:
“What are your top 3 priorities for this year in your role?”
“What’s getting in the way of execution?”
“What would success look like if you could fix this?”
If you can support them in achieving their highest level goals or solve problems that are top of mind – ask them to sponsor a deeper discovery with their team and get their commitment to meet with you for a readout when discovery is complete.
Step 3: Drop Down
Remember: At this level, your job isn’t to sell. Don’t pitch, just listen for friction:
- Processes, tools, and workflows that are broken.
- Specific quotes that you can bring back to the executive.
- Time and labor costs involved with the status quo.
After my meeting with the executive, I was invited into the operations and met with marketing, IT and their salespeople:
- I uncovered that their IT team was building all their solutions in-house and that was driving a lot of inefficiencies.
- Several key projects were stalled and those that were delivered were past the timeline and budget.
- That put their business priority of transforming the customer experience at risk because they couldn’t possibly support this level of transformation in-house.
The discovery with the department leads helped us design a full transformation of their experience with a complete platform instead of a simple point solution.
Why? Because we understood how each department was struggling to support the overall business goals from the executive at the top.
Step 4: Bounce Back Up
Now it’s time to combine the executive vision, the drop down discovery, and your transformation proposal into one executive summary and business case.
We proposed an 8-figure platform transformation that unified their CRM, marketing, operations, and reporting.
Most importantly, the platform enabled a future where their sales team would not have to be dependent on IT to drive further innovation as it would enable a no-code environment where they could build applications directly.
This is the key to Yo-Yo Selling: Everything from the drop down discovery to the business case ties directly back to the executive vision that you learned in the first call.
That's a Wrap!
Yo-Yo Selling helped me go from earning $240K/year to 720K/year in tech sales. But here’s the thing: strategy alone isn't enough.
To consistently close big deals, you need more than skills.
- You need the right mindset to meet confidently with executives.
- You need the discipline to prospect to power daily.
- You need patience to trust the process.
- You need habits that keep you focused and productive.
That’s why mindset, habits, and skills are all part of the free masterclass I put together for sellers who want to break into the top 1%.
If you’re serious about mastering enterprise sales, this will be a game-changer.
See you inside:
👉 Watch the full free training here
