As a mayor, you’re likely facing the challenge of selecting the right technology partner to modernize your city’s digital infrastructure. In today’s rapidly evolving digital landscape, the stakes have never been higher—with GovTech deal volumes exceeding $20 billion in 2025 and AI transforming how municipalities serve their residents. This comprehensive guide will walk you through the ten essential questions that will help you identify a vendor who can truly deliver on their promises and become a long-term partner in your city’s success.
Why Vendor Selection Matters More Than Ever
Municipal leaders across the country are grappling with unprecedented technological change. If you’re a mayor looking to modernize your city’s website, implement smart city solutions, or upgrade legacy systems, you’re not alone. Recent studies show that 58% of government executives prioritize accelerating AI and data adoption, yet only 26% currently have integrated AI systems. The gap between aspiration and implementation often comes down to one critical factor: choosing the right technology partner.
The wrong vendor can lead to cost overruns, security vulnerabilities, poor citizen adoption, and years of frustration. The right partner, however, becomes an extension of your team—helping you navigate compliance requirements, scale with your city’s growth, and deliver measurable improvements in citizen satisfaction.
The 10 Essential Questions
1. How Do You Embed Security Throughout Your Organization?
Why This Matters: Cyberattacks on local governments have increased by 50% over the last five years. Your vendor’s security posture isn’t just about technology—it’s about organizational culture.
What to Ask:
- Do you have a dedicated Chief Information Security Officer (CISO) on your executive team?
- How do you continuously update security protocols and train employees on emerging cyber threats?
- Do you operate a physical Security Operations Center (SOC) for 24/7 monitoring?
- What is your process for proactive vulnerability patching?
Red Flags: Vendors who can’t articulate a comprehensive security strategy or lack basic certifications like FedRAMP, NIST, or ISO 27001 should be eliminated immediately. These certifications are foundational—their absence signals a fundamental lack of security priority.
2. How Is Your Software Developed and Tested?
Why This Matters: The development process determines whether new features introduce vulnerabilities or strengthen your digital infrastructure.
What to Ask:
- Do you conduct dynamic application scanning to identify weaknesses in running applications?
- How frequently do you perform penetration testing to simulate cyberattacks?
- What is your software release cycle, and how do you ensure quality control?
- How can our city participate in your product development roadmap?
Look For: Vendors who invest at least 10-15% of annual revenue in research and development demonstrate a commitment to innovation. Ask about their R&D investment and how they incorporate customer feedback into product evolution.
3. What Is Your Track Record with Municipalities Like Ours?
Why This Matters: Government technology has unique requirements around compliance, accessibility, and public accountability. Experience matters.
What to Ask:
- Can you provide references from cities of similar size and complexity?
- What specific challenges have you helped other municipalities overcome?
- How do you measure and demonstrate ROI for your government clients?
- What is your average client retention rate?
Best Practice: Speak directly with at least three current clients. Ask about implementation experience, ongoing support responsiveness, and whether the vendor delivered on their promises. Don’t just accept curated case studies—insist on real conversations with real users.
4. How Will Your Solution Integrate with Our Existing Systems?
Why This Matters: Approximately 30% of government agencies use incompatible or proprietary technology stacks. Integration challenges can derail even the best-intentioned projects.
What to Ask:
- What APIs do you offer for integration with our current systems?
- How do you handle data migration from legacy platforms?
- Can you provide a detailed integration plan specific to our technology environment?
- What happens if integration proves more complex than anticipated?
Critical Detail: Request a shared responsibility matrix that clearly defines who is responsible for each aspect of integration, data security, and ongoing maintenance.
5. What Does Your Support Structure Look Like?
Why This Matters: The relationship doesn’t end at launch. Ongoing support determines whether your investment delivers long-term value or becomes a source of constant frustration.
What to Ask:
- What is your Service Level Agreement (SLA) for support response times?
- Who responds to support requests—entry-level agents or senior engineers?
- Are there different support tiers, and what do they cost?
- How do you handle after-hours emergencies?
- What training do you provide for our staff?
Negotiate Wisely: If a vendor cannot fully meet your support needs, ask whether they offer financial refunds or service credits. Build accountability into the contract from day one.
6. How Do You Handle Data Privacy and Compliance?
Why This Matters: Municipal websites handle sensitive resident data. Non-compliance with ADA, Section 508, or data privacy regulations can result in costly lawsuits and loss of federal funding.
What to Ask:
- What data do you collect, and where is it stored?
- Who has access to our data, and how is that access authenticated?
- Do you have written policies prohibiting the sale of data to third parties?
- How do you ensure ADA and WCAG compliance?
- What is your data breach response plan?
For Cloud Solutions: If you’re considering cloud-based tools that handle Controlled Unclassified Information (CUI), FedRAMP compliance is non-negotiable. Ask for recent risk assessment results and audit reports.
7. What Is Your Financial Stability and Long-Term Viability?
Why This Matters: Selecting a vendor who goes out of business or gets acquired can leave your city stranded with unsupported technology.
What to Ask:
- What is your company’s financial health and funding situation?
- Are you profitable, or what is your path to profitability?
- Have you been acquired or are you planning to be acquired?
- What is your product roadmap for the next 3-5 years?
Due Diligence: For privately held companies, request yearly financials or at minimum, information about recent funding rounds. Publicly traded companies should provide investor relations materials.
8. How Do You Stay Current with Emerging Technologies?
Why This Matters: The GovTech landscape is evolving rapidly, with AI, automation, and citizen engagement tools transforming service delivery. Your vendor should be ahead of the curve, not playing catch-up.
What to Ask:
- How are you incorporating AI and machine learning into your platform?
- What percentage of your customers are actively using your newest features?
- How do you promote user adoption of new releases?
- What differentiates your platform from competitors?
Forward-Thinking Indicator: Vendors who can articulate a clear vision for how emerging technologies will benefit your specific use case—not just generic AI buzzwords—demonstrate genuine innovation leadership.
9. What Is the Total Cost of Ownership?
Why This Matters: The lowest initial price often leads to the highest long-term costs due to hidden fees, poor performance, or expensive customizations.
What to Ask:
- What is included in the base price, and what costs extra?
- How do you handle software updates—are they included or additional?
- What are the costs for training, customization, and integration?
- Are there per-user fees, and how do they scale?
- What happens when our contract comes up for renewal?
Calculate TCO: Work with your finance team to calculate the total cost of ownership over 5 years, including implementation, training, support, updates, and potential customization. Compare this across vendors, not just the sticker price.
10. How Will You Help Us Measure Success?
Why This Matters: Without clear metrics, it’s impossible to demonstrate ROI to your city council or justify continued investment.
What to Ask:
- What key performance indicators (KPIs) do you recommend we track?
- How do you help customers measure and prove ROI?
- What analytics and reporting capabilities does your platform provide?
- Can you provide benchmarks from similar municipalities?
Success Framework: The best vendors will work with you to establish baseline metrics before implementation and then track improvements in areas like citizen satisfaction, staff efficiency, website traffic, and service request resolution times.
Making Your Decision
After asking these ten questions across multiple vendors, you’ll have the information needed to make an informed decision. Create a weighted scoring rubric based on your city’s priorities—perhaps security and support are more important than cutting-edge features, or maybe integration capabilities are your top concern.
Involve stakeholders from across your organization in the evaluation process. Your IT director, finance team, department heads, and even front-line staff who will use the system daily should have input. The most successful implementations happen when everyone feels ownership of the decision.
Ready to Find Your Ideal Technology Partner?
At mycitygov.com, we understand the unique challenges mayors face when modernizing municipal technology. Our platform is built specifically for local government, with robust security, intuitive content management, and dedicated support from a team that knows the public sector inside and out.
We welcome tough questions—in fact, we encourage them. Because we know that informed decision-making leads to successful partnerships and better outcomes for the communities we serve together.
Contact mycitygov.com today for a free consultation. Let’s discuss your city’s specific needs and explore how our solutions can help you achieve your digital government goals. No pressure, no sales tactics—just honest conversation about how we can support your vision for your community.
