Insights from Stephen Steers’s Business of Software AMA
Stephen Steers is not your typical sales consultant. A world traveler, stand-up comic, and author of Superpower Storytelling, he’s helped companies close high-value deals by shifting their sales approach from feature-dumping to context-driven conversations.
At his recent AMA at the Business of Software Conference, Stephen dropped a masterclass in sales strategy, sprinkled with humor, honesty, and hard-won wisdom.
Here’s what you need to know.
Sales Isn’t Just Talking: It’s Listening with Purpose
Stephen’s approach, called “Context Selling,” is built around understanding the client deeply before pitching anything. He teaches the OC-GC method:
- Opening – Set the agenda and expectations.
- Create the Gap – Understand where the customer is vs. where they want to be.
- Closing – Guide the conversation toward a next step.
“If you don’t ask for a next step, you’re not in a sales conversation… You’re in a chat.”
Key Takeaways from Stephen’s Session
1. Storytelling in Sales = Strategic Framing
Stories are powerful, but not in the fluffy, fairy-tale way. For Stephen, stories in sales should:
- Show how you’ve solved a real problem.
- Include measurable business outcomes.
- Be relevant to the buyer’s specific role.
“If you’re talking to a CEO, tell a revenue-focused story. If you’re talking to operations, make it about efficiency.”
2. Businesses Buy for 4 Reasons
Stephen broke down the 4 core business drivers that every sales pitch should touch:
- Make money
- Save money
- Increase efficiency
- Mitigate risk
Know which one your product hits, and tailor your story accordingly.
3. Use Powerful Questions to Discover Value
Instead of guessing what your solution is worth, ask questions that reveal it:
- What are your annual goals?
- How many clients do you need to hit that?
- What’s in the way of achieving that?
These answers tell you the size of the problem, and how valuable your solution is.
“Whatever they say is true. Whatever you say, you have to defend.”
4. Value-Based Pricing > Project-Based Pricing
Stephen warned against pricing complexity. Trying to price every deal differently creates confusion and kills momentum.
- Go for enterprise-wide licensing with clear ROI logic.
- Tie pricing to the value you deliver, not just the effort you expend.
5. Keep It Simple, or Lose the Deal
When pricing or delivery models are too complex, customers opt out—even if you have the best product.
“If you make it hard for me to buy, I’ll find someone who doesn’t.”
6. Follow-Up Isn’t Just Support: It’s Sales
Stephen emphasized account management as a continuation of the sales process. Why?
- You can upsell and cross-sell when you know your customer’s evolving needs.
- You maintain loyalty and reduce churn.
Bonus Insight: Logic Doesn’t Sell, Emotion Does
One attendee noticed some prospects cared more about features than stories. Stephen’s take?
Even logic-driven buyers make emotional decisions, they just justify them with numbers.
So don’t ditch storytelling. Instead, anchor it in their business objectives (revenue, risk, efficiency) and speak their language.
Final Thoughts
Stephen Steers brought more than just charisma to his AMA, he brought clarity. Whether you’re a founder, sales rep, or someone who “wears a lot of hats,” his message was the same:
Stop guessing. Start asking better questions. Frame your solution around the value you deliver. And always, always keep it human.
📚 Want more insight from Stephen? Watch his talks in our library here, or check out the full AMA replay via Business of Software.