10 Questions Every Mayor Should Ask a Potential GovTech Vendor

As a mayor or city administrator, you’re likely facing the challenge of selecting the right technology partner to modernize your municipality’s digital infrastructure. In today’s rapidly evolving digital landscape, the stakes have never been higher—your choice will impact citizen services, operational efficiency, and your city’s ability to meet rising expectations for years to come. This comprehensive guide will walk you through the essential questions that separate exceptional govtech vendors from those who simply can’t deliver.

Why Vendor Selection Matters More Than Ever in 2026

The govtech market has reached unprecedented maturity in 2026, with over $20 billion in deal volume recorded in 2025 and continued momentum into this year. With hundreds of vendors competing for your attention, making the right choice requires more than reviewing glossy brochures or attending a few demos. Municipal leaders who ask the right questions upfront avoid costly mistakes, implementation failures, and the nightmare of being locked into unsuitable technology.

Recent trends show that successful municipalities are moving beyond simply seeking the lowest bid. Instead, they’re prioritizing overall value, long-term partnerships, and vendors who demonstrate genuine commitment to the unique needs of local government. The shift toward AI integration, enhanced cybersecurity, and practical application of technology means your vendor selection process must be more rigorous than ever.

The 10 Critical Questions to Ask Every GovTech Vendor

1. How Is Security Embedded in Your Organizational Culture?

Security isn’t just a feature—it’s a fundamental requirement for any government technology. Ask vendors to explain how security is woven into their company culture, not just their product. Look for evidence of:

• Ongoing security training for all employees, not just IT staff
• A dedicated internal security team that continuously evolves protocols
• Regular employee education on threat identification and prevention
• A physical Security Operations Center (SOC) for 24/7 monitoring

Red flag: Vendors who treat security as an afterthought or can’t articulate their security culture clearly should be eliminated from consideration immediately.

2. What Certifications and Compliance Standards Do You Meet?

Don’t accept vague assurances about security. Demand specifics about certifications and compliance frameworks:

• FedRAMP compliance for any solution processing Controlled Unclassified Information (CUI)
• NIST framework adherence for cybersecurity standards
• ISO certifications demonstrating international security standards
• Section 508 and WCAG compliance for accessibility requirements

Ask to see documentation, not just claims. Vendors without these foundational certifications may not prioritize security or compliance, putting your municipality at risk of data breaches, lawsuits, and loss of federal funding.

3. Does Your Executive Team Include a Chief Information Security Officer (CISO)?

The presence of a CISO in the vendor’s executive leadership team signals that security is a top-level priority, not just an operational concern. This role ensures:

• Security considerations influence strategic business decisions
• Customer data protection receives executive-level attention
• The company stays ahead of emerging threats and vulnerabilities
• Resources are allocated appropriately for security initiatives

If a vendor doesn’t have a CISO or equivalent executive security leader, question whether they’re truly prepared to protect your sensitive municipal data.

4. How Do You Handle Software Updates, Customization, and Integration?

Understanding the practical, day-to-day operation of the technology is crucial:

Software Updates:

• How frequently are updates released?
• Are updates automatic (SaaS) or do they require manual implementation?
• What are the associated costs for updates and upgrades?
• How do you communicate upcoming changes to customers?

Customization:

• Can the software be customized to match our specific workflows?
• Who handles customizations—your team or ours?
• What are the costs and timelines for custom development?

Integration:

• How does your solution integrate with our existing systems?
• What APIs are available for data sharing?
• Do you offer Single Sign-On (SSO) capabilities?
• How do you vet your integration partners?

Vendors who offer rigid, one-size-fits-all solutions rarely work well for municipalities with unique processes and legacy systems.

5. What Is Your Track Record with Municipalities Similar to Ours?

Experience matters in govtech. Request specific references from municipalities of similar size, budget, and complexity:

• Ask for at least 3-5 current clients you can contact directly
• Inquire about implementation timelines and challenges they faced
• Understand how the vendor supported them through difficulties
• Learn about the long-term relationship and ongoing support quality

Pro tip: Don’t just accept the vendor’s curated reference list. Search for other municipalities using their technology and reach out independently. Online reviews, conference discussions, and peer networks can reveal insights vendors won’t volunteer.

6. What Is Your Financial Health and Long-Term Viability?

Your technology partner needs to be around for the long haul. For privately held companies, don’t hesitate to ask:

• What are your yearly financials and revenue trends?
• How are you funded, and what are your future funding plans?
• What percentage of annual revenue is invested in R&D?
• What is your customer retention rate?

A vendor’s financial instability can leave you stranded with unsupported technology, forcing costly migrations and disrupting citizen services. The 2026 GovTech 100 companies have collectively raised $11.1 billion and average nearly 19 years in operation—look for similar indicators of stability.

7. How Do You Measure and Help Us Prove ROI?

Municipal budgets are tight, and every investment must be justified. Ask vendors:

• What metrics do you use to measure success?
• How do you help customers quantify ROI?
• What efficiency gains have similar municipalities achieved?
• Can you provide case studies with specific, measurable outcomes?

Vendors who can’t articulate clear ROI or provide concrete examples of value delivered should raise concerns. Look for partners who understand municipal budget constraints and can help you build compelling business cases for council approval.

8. What Is Your Approach to Customer Support and Service Level Agreements?

Even the best technology encounters issues. Understanding support quality before signing a contract is essential:

• What are your SLA response times for different severity levels?
• Who responds to support requests—customer service reps or senior engineers?
• What support channels are available (phone, email, chat, portal)?
• Are there different support tiers, and what do they cost?
• How do you handle after-hours emergencies?

Request to speak with the actual support team, not just sales representatives. Ask current customers about their real-world support experiences, including response times and problem resolution effectiveness.

9. How Do Customers Participate in Your Product Roadmap?

Your needs will evolve, and your vendor’s product should evolve with them. Inquire about:

• How customer feedback influences product development
• Whether you’ll have a voice in prioritizing new features
• How often the product roadmap is updated and shared
• What mechanisms exist for submitting feature requests

Vendors who develop in isolation, without customer input, often build features that look impressive in demos but fail to address real municipal needs. Look for partners who view customers as collaborators in product evolution.

10. Can We Start with a Pilot Program or Proof of Concept?

Before committing to a full implementation, ask about smaller-scale validation:

• Do you offer pilot programs for new customers?
• What would a proof of concept look like for our specific use case?
• What are the costs, timelines, and success metrics for a pilot?
• How do we transition from pilot to full implementation if successful?

Vendors confident in their solutions will welcome the opportunity to prove value in your specific environment. Those who push for immediate, large-scale commitments may be more interested in closing deals than ensuring customer success.

Beyond the Questions: Evaluating Vendor Responses

Asking these questions is only the first step. Pay attention to how vendors respond:

• Transparency: Do they answer directly, or do they deflect and obfuscate?
• Specificity: Do they provide concrete examples and documentation, or vague assurances?
• Understanding: Do they demonstrate knowledge of municipal government challenges?
• Patience: Are they willing to take time to address your concerns thoroughly?

The best vendors will welcome tough questions because they’re confident in their answers. Those who become defensive, evasive, or dismissive likely have something to hide.

Preparing Your Team for Vendor Evaluation

Before engaging with vendors, ensure your internal team is aligned:

• Define Your Needs: Clearly articulate what problems you’re trying to solve
• Identify Stakeholders: Include IT, finance, legal, department heads, and end-users
• Establish Evaluation Criteria: Create weighted scoring rubrics for objective comparison
• Set Budget Parameters: Understand total cost of ownership, not just initial costs
• Document Requirements: Create detailed technical and functional specifications

This preparation ensures you ask consistent questions across vendors and can make objective comparisons.

The Bottom Line: Partnership Over Purchase

Selecting a govtech vendor isn’t about buying software—it’s about choosing a long-term partner who will support your municipality’s digital transformation journey. The right partner will:

• Understand the unique challenges of local government
• Prioritize security and compliance without compromise
• Provide transparent, responsive communication
• Demonstrate financial stability and commitment to innovation
• Offer flexible, scalable solutions that grow with your needs

By asking these 10 critical questions and carefully evaluating responses, you’ll be equipped to make an informed decision that serves your community for years to come. Don’t rush the process, don’t settle for vendors who can’t answer these questions satisfactorily, and don’t let budget constraints force you into partnerships that will ultimately cost more in the long run.

Take the Next Step Toward Digital Transformation

The journey toward municipal technology modernization requires careful planning and the right technology partner. Municipal leaders who take action now will be better positioned to serve their communities effectively and meet the rising expectations of 21st-century citizens.

At mycitygov.com, we specialize in helping local governments navigate these digital transformations successfully. Our team understands the unique challenges mayors and city administrators face, and we’re committed to providing secure, scalable, and user-friendly solutions backed by exceptional support.

Ready to modernize your municipal website and digital services? Contact mycitygov.com for a free consultation and discover how we can help transform your digital presence while ensuring security, compliance, and long-term value for your community.