Whether a corporate strategic plan is driving your search for a custom software vendor, or your legacy system needs life support, finding a vendor that aligns with your vision and budget does not have to be an arduous task. 

Often when business executives begin researching custom software vendors, they’re looking for partners who can deliver value, minimize risk, and support long-term growth.  But software vendors often speak a different language and being able to cut through the jargon is critical to project success. 

 After 20 years in business, supporting some of the world greatest IT teams, we have compiled a guide, including some key questions designed to help executives with the decision-making process. 

Questions and Considerations: 

Proven Expertise & Industry Experience 

Alignment is essential: 

• Has this vendor worked with companies in our industry? 

• Do they understand our business model, regulations, and pain points? 

Why it matters:

Industry experience means faster ramp-up times, fewer communication gaps, and a higher chance of success. Executives often search for case studies, client lists, or domain-specific certifications. 

Portfolio and References 

Visible proof of success: 

• What projects has this vendor completed? 

• Are there testimonials or client references? 

• Do they have experience with similar challenges? 

Why it matters:

Seeing a strong track record reassures decision-makers that the vendor can handle complexity and deliver results. 

Technical Capability & Scalability 

Determining the right technical fit is critical: 

• Can the vendor build scalable, secure, and performant software? 

• Do they have expertise in relevant tech stacks (e.g., C/C++, .NET, Java, Python, PHP,  mobile, cloud, APIs, etc.)? 

• Can they handle both legacy integrations and modern platforms? 

Why it matters:

The wrong technical fit leads to rework, instability, or project failure. Executives often want vendors that can flex as their needs evolve. 

Project Management & Communication 

Key concerns include: 

• How will the project be managed? Agile? Waterfall? Hybrid? 

• Can we as a client manage the project? 

• Will there be a dedicated point of contact? 

• Is the vendor responsive, transparent, and easy to work with? 

Why it matters:

Even great code is meaningless if a project isn’t delivered on time, on budget, and with clear communication. 

Cost and Value 

Understanding the price and the hidden costs: 

• What is the total cost of ownership (TCO)? 

• Does the vendor deliver ROI through efficiency, automation, or competitive advantage? 

• Is their pricing models clear and fair (fixed bid, hourly, retainer)? 

Why it matters:

They need confidence that the investment will pay off and not spiral into hidden costs or extended timelines. 

Contracting 

Understanding the nuances of software specific contracting: 

• Is the contracting process straightforward? 

• What are their term lengths and types? 

• Will the vendor sign an NDA? 

• Code ownership, what are the options? 

Why it matters:

Executives need confidence that there are mutual protections in place. 

Support, Maintenance, and Long-Term Partnership 

They ask: 

• What happens after launch? 

• Do you offer ongoing support, updates, and maintenance? 

• Are you equipped to grow with us long-term? 

Why it matters:

our software is a major part of your business, you need a reliable partner for the long haul. 

Security & Compliance 

For regulated industries especially, questions include: 

• How do you handle data security? 

• Are you compliant with HIPAA, GDPR, PCI, etc.? 

Why it matters:

One security misstep can damage reputation, cause legal trouble, or shut down operations. 

Innovation & Strategic Thinking 

Forward-thinking execs want to know: 

• Will this vendor bring ideas, not just execution? 

• Can they advise us on technology trends or process improvements? 

Why it matters:

Nontechnical executives, are often seeking insight—not just coding—especially when custom software supports digital transformation efforts. 

Final Thought: 

Executives don’t just want code. They want confidence. They’re searching for a vendor they can trust—one that understands their business, delivers results, and grows with them. Custom software isn’t just a technical challenge—it’s a business-critical investment, and the right vendor can make or break its success. If you managed to get this far and still have questions, reach out, our Advisory Division  offers a no pressure 30-minute consultation.