To thrive in this new era, you must become a detective, peering deep into the heart of your customer's world. You need to uncover their needs, goals, challenges, and the pain points that keep them up at night. To achieve this, ask the right questions, listen actively, and, most importantly, empathize with your customer. You're not just selling software; you're a problem solver. Dive into research about their industry, competitors, and emerging trends. Understand who holds the decision-making strings and who influences the final call.

Most often customers who compare your software to OSS will be particularly interested in: 1. Pricing - how do you fare against the cost of hosting OSS themselves. Highlight that the cost would not just be about hosting it themselves, but they will also need to spend valuable resource time in deploying and running it themselves. 2. Support & New Features: It's far easier to request relevant features from an enterprise company than convincing the open source community to do something for your enterprise. Highlight how your team can support and enable new functionalities that align with the customer. 3. Differentiation: What features does your software offer that OSS doesn't and how much more value does it bring to the table vs the price.

With OSS, there's always a chance of project being abandoned unless its a well funded one. Plus, quality support on OSS is almost non-existent. Build trust and credibility with your customer on the basis of how you offer dedicated support if it exists. Share case studies and customer stories on how you helped a customer solve for a challenge with on-demand feature fulfilment. Use quality testimonials to back up your story. Highlight the fact that your company is invested in customer success because that's the only way you win in the market. You can also share a long-term product roadmap with the customer to share where your product is headed & that they know what to expect vs. the uncertainty that comes with OSS project.

Familiarize yourself with the open source software ecosystem, its strengths, and limitations. Explore partnerships or integrations with open source projects to provide overall solutions. Emphasize the unique benefits of your proprietary software, such as support, scalability, and security. Focus on understanding clients' specific needs and tailoring solutions to address them. Offer additional services like training, customization, or consulting to differentiate your offering. Ensure your software has robust customer support and maintenance to build relationship. Be competitive in pricing while demonstrating the long-term value of your solution. Highlight security features and compliance standards to assure clients of data protection.

On the face of it, both have their pros and cons. There are countless articles swaying companies toward the other. In my experience, customers don't just evaluate software costs in terms of upfront/initial costs. They look at the bigger picture and also assess hidden cost elements like time to value, risk, support and trust. All of these play a massive role in understanding the actual total cost of ownership. Enterprise software usually helps mitigate these hidden elements as they are backed by years of R&D, a dedicated support team and a company that wants its customers to be successful.