Tsahala David on Sales Strategy, AI, and Revenue Growth

Selling has always been at the heart of business growth—but how we sell, who sells, and what customers expect has changed dramatically. On this episode of On the Brink with Andi Simon, I spoke with Tsahala David, CEO of Great Revenue, a sales consulting firm that helps B2B software companies grow smarter and faster. With an extraordinary background—MIT MBA, tech founder, and sales leadership roles at IBM and Salesforce—Tsahala has seen sales from every angle. Her story and insights reveal not just how to grow revenue but how to thrive in a new era of sales transformation

From Startup Founder to Sales Leader

Tshala’s journey began in Israel, where she completed military service and studied psychology before shifting into computer science. After founding her own tech company in her twenties, she confronted an early challenge many entrepreneurs face: defining her role. At first reluctant to call herself “CEO,” she quickly realized that imposter syndrome had to be shed—because if you’re running the business, you are the CEO

That early startup experience gave her first-hand knowledge of the uphill battle founders face in selling products, building teams, and convincing investors. Seeking more tools, she went to MIT for her MBA, then built a 20-year career in sales at global giants like IBM and Salesforce, closing multi-million-dollar deals with clients like Wells Fargo and Cisco.

At Salesforce, she learned what she calls the “power of sparkle”—the way a company can attract talent, customers, and attention by combining strategy with personality and brand charisma. These lessons now fuel her work at Great Revenue, where she helps companies align their sales strategies with today’s market realities.

Common Mistakes in Startup Sales

One of Tsahala’s most valuable contributions is diagnosing the mistakes founders and sales leaders make at different growth stages.

• Early-stage startups often believe that signing a few reseller “partners” means they have a sales team. But, as Tshala warns, relying on partners who only earn commission when they sell means sales rarely happen. The real cost isn’t money—it’s lost time, and in startups, six months of delay can kill your competitive advantage
• Later-stage companies often get compensation plans wrong. She shared a case where salespeople were paid less for online orders than phone orders. Predictably, reps discouraged online buying and insisted clients call them—hurting profitability and wasting resources. The lesson? Follow the money. Salespeople respond to incentives, so design compensation plans with the outcomes you want
• Sales management is another weak spot. Too often, managers don’t require reps to prepare for pipeline meetings. Tshala recommends using simple forms that force reps to answer key questions—deal size, decision makers, last contact, close date. This not only helps managers track progress but also helps sellers spot gaps in their deals

The Role of AI in Sales

Naturally, our conversation turned to AI in sales. Tsahala sees tools like ChatGPT as game-changers for research and preparation. Instead of spending hours digging through reports, salespeople can instantly access a company’s strategy, leadership, and metrics.

But there’s a catch: weak sellers often use AI as a crutch, staying at a generic level. Strong sellers know to go deeper, asking sharper questions and tailoring insights to the customer’s specific needs. AI, Tshala argues, empowers strong sellers but won’t rescue weak ones

The future belongs to those who combine technology with human curiosity, empathy, and problem-solving.

Shifts in Buyer Behavior

Another theme we explored was the dramatic shift in how buyers engage with sellers. Older generations may remember sitting across the table until a contract was signed. But today’s buyers often don’t work in offices, don’t answer phones, and rely on digital channels to research solutions.

Events are no longer centralized; instead, buyers connect through fragmented online communities—from LinkedIn groups to Discord servers. That means marketing now owns much of the top of the funnel, while sales must focus on converting leads and building trust. Sellers today must immerse themselves in buyers’ digital worlds, positioning themselves not just as vendors but as collaborators in problem-solving

Key Takeaways for Sales Leaders

As we wrapped up our conversation, Tsahala emphasized that sales is a profession, not a side hustle. Everyone thinks they know how to sell—after all, we’ve all sold something, even if just a used car or lemonade stand. But true sales success requires expertise, structure, and strategy.

Here are her top three lessons for sales leaders and entrepreneurs:

1. Don’t go it alone. Sales consulting isn’t optional—it’s an investment in avoiding costly mistakes.
2. Design incentives wisely. Compensation plans drive behavior. Align them with your business goals.
3. Embrace change. Buyer behavior, sales roles, and technology are evolving. Those who adapt will thrive

Why This Matters Now

We are living through a great transformation in sales. Marketing and sales are no longer siloed; collaboration is essential. AI accelerates preparation but cannot replace human insight. And customer expectations continue to evolve.

For CEOs, founders, and sales leaders, Tsahala David’s message is clear: if you want revenue growth, you must rethink your approach to sales. Invest in your people, design smart processes, and leverage technology thoughtfully.

Sales isn’t just about closing deals anymore—it’s about creating value, building trust, and collaborating with buyers in ways that meet them where they are.

Watch our interview on YouTube

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From Observation to Innovation,

Andi Simon, PhD

CEO | Corporate Anthropologist | Author
Simonassociates.net
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