Do You Need a Website Support Retainer? Red Flags and Where Web Agencies Can Actually Provide Value

Interested in listening or watching the discussion:

• YouTube: Website Support Is Broken — Here’s the Better Way
• Spotify: From Maintenance to Value: Rethinking Website Support Models

Introduction

If you're a CMO or technology leader or marketing manager or business owner paying $3,000 to $15,000 per month for vendor support, ask yourself: what are you actually getting? For many organizations, the answer is uncomfortable. That hefty monthly retainer buys slow response times on simple updates, vague reporting with no clear metrics, and a nagging feeling that you're locked into a relationship designed to keep you dependent. Often, what you're really purchasing is a bundle of support services and management, but without the operational oversight or proactive solutions that actually drive results.

The traditional agency support model has a dirty secret: it's built on backwards incentives. When your vendor makes money by billing hours to fix problems, they have little motivation to build solutions that eliminate those problems. It's time to rethink what effective support looks like—and whether you need it at all.

The Broken Economics of Traditional Web Support Retainers

Traditional support retainers operate on a fundamentally flawed premise. As the hosts point out, "When agencies profit from your problems, your problems become the product." This isn't hyperbole—it's basic economics.

Most retainers are structured around billable hours for maintenance, bug fixes, technical patches, and resolving technical issues. The vendor thrives when there are issues to resolve. Extended timelines mean extended billing cycles. "Quick fixes" become recurring revenue streams because permanent solutions would kill the golden goose.

Many agencies offer their services through various plans, packaging support and maintenance to fit different business needs and budgets. These plans often include ongoing work such as managing and updating plugins, which are essential for site functionality, security, and compatibility, especially within a content management system like WordPress.

Consider the absurdity: organizations report paying premium hourly rates just to update website copy—a task that should take minutes but requires submitting a ticket, waiting for a response, and burning through retainer hours. As one host notes, "It surprises me… we're constantly having these conversations" about websites that weren't designed with client self-sufficiency in mind.

The model becomes even more problematic with proprietary systems. If a firm owns its own homegrown content management system (CMS) platform, "that is probably like cover, duck and cover and run," one host warns. These vendors are simultaneously running a product business and a services business, selling you the platform, the hosting, and the services to maintain what they built on that platform. It's a recipe for conflict of interest—what the hosts call "digital slumlords" holding clients captive on subscription platforms they control.

Red Flags: Signs You're in a Dependency-Driven Relationship

How do you know if you're trapped in one of these backwards relationships? Watch for these warning signs:

Slow Response Times on Simple Updates: The ratio of simplicity to response time reveals everything. If routine content updates require multiple weeks and multiple billable meetings, something is broken. One example shared: a vendor burning most of the retainer budget just on scoping calls, with eight people on two-hour calls racking up billable hours before any actual work begins. Delays in handling feature requests are another red flag—if new features or improvements take ages to implement, your support is lacking.

Knowledge Hoarding: Lack of documentation is a massive red flag. If your vendor hasn't provided comprehensive documentation about your technology stack, they're deliberately keeping you dependent. As the hosts discovered in a recent client conversation, some vendors don't create any documentation at all—even for complex digital transformation projects. The absence of regular audits can hide issues like broken links and problematic external links, which can negatively impact user experience and SEO.

Opaque Reporting: Vague monthly reports showing "hours used" without clear metrics tied to business outcomes. Everything feels like a black box, and you can't see what's actually being worked on or why simple changes take so long. Unused hours are a common issue in unclear retainer reports, with no transparency on how hours are tracked or what happens to hours that aren't utilized.

Proprietary Platform Lock-In: If you're on a vendor's homegrown CMS, you're handcuffed to their technology. These platforms can't compete with billion-dollar companies like Webflow, WordPress, or Shopify, yet you're paying both subscription fees and service fees with no viable migration path.

Finally, the absence of regular maintenance—such as scheduled updates, security checks, and backups—is a clear sign of a problematic relationship.

What Value-Driven Website Maintenance Support Actually Looks Like

Value-driven retainers flip the traditional model entirely. Instead of billing for maintenance, they focus on measurable improvement and strategic enablement.

The shift starts with treating your website as a product, not a static asset. "When you launch the website, that's really day one," the hosts explain. The question becomes: how do we maximize this investment through continuous optimization? This means keeping your website content updated, maintaining the site through regular updates, and ensuring the website is always optimized for performance, security, and search engine visibility.

Effective retainers include kickoff meetings to establish objectives, quarterly check-ins to align priorities, and a collaborative approach where "those hours are there to be utilized… for the right things." The focus moves from firefighting to strategic initiatives:

• Optimization and A/B Testing: Implementing frameworks that allow you to prototype, test, and choose the best direction for new initiatives, continually optimize functionality, and keep the website optimized for users and search results.
• Knowledge Transfer: Documentation, training, and access that enables your team to self-manage, supporting ongoing website maintenance and wordpress maintenance as part of comprehensive maintenance services.
• Strategic Enablement: Spending dollars on accessibility compliance, conversion optimization, SEO lift, or improving user experience for visitors and users—not ticket queues. This includes adding new features, ongoing development, marketing support, management support, and enabling more digital marketing and digital marketing strategies. A structured plan guides these efforts, ensuring your website's design, web design, and website design remain current and effective across all devices, including mobile devices.
• Proactive Monitoring: Using tools to track your website's performance, monitor for security vulnerabilities, and ensure the site running smoothly. Regular updates and audits help maintain compliance with accessibility standards and mitigate risks.

This approach often means clients don't need ongoing support at all. The hosts cite Django projects they built years ago that "are still running, still secure, and we don't hear anything from them because they were just built in a way that didn't need that level of support."

The ROI of Enablement Over Dependency

Here's the paradox: when you work to make clients self-sufficient, they often stay longer. As one client told the hosts: "You're essentially working yourselves out of the job by making us self-sufficient." The client kept them on retainer anyway—not for maintenance, but for strategy, optimization, and growth.

When clients see ROI in strategic enablement and ongoing development rather than firefighting, the entire relationship changes. They stop nickel-and-diming support hours because they trust the partnership is aligned with their success. The retainer becomes an investment in growth, not a tax on keeping the lights on.

For organizations with understaffed teams or bandwidth constraints, including small businesses and small business owners, the right support model actually delivers cost savings. As the hosts point out, it's inefficient to have intermediate or senior-level employees managing routine website updates when a dedicated developer or a team of developers can provide more effective support. A value-driven vendor partnership that includes development services can be more cost-effective than internal resources—but only when structured correctly.

Do You Actually Need a Support Retainer?

The hosts recommend discussing retainers at the end of a project, not the beginning: "By then we will know what level of support you need that will actually fit your business." Many successful projects don't need ongoing support at all, but having a maintenance plan or structured plan for ongoing website support can be essential for some businesses.

Consider this decision framework:

You probably need support if:

• Your sites or platform are live, evolving assets with continuous optimization needs
• You're running a product (not just a brochure website) with complex integrations
• You lack internal bandwidth or expertise for strategic initiatives
• You are launching a new website and want to ensure ongoing updates, security, and performance through a maintenance plan

You probably don't need support if:

• Your sites are relatively static with infrequent updates
• Your platform is stable and built on solid infrastructure (like Webflow, which handles security, patches, and uptime at scale)
• Nothing urgent breaks when you imagine not having the retainer

Run a cost-benefit analysis. What's the worst-case scenario without support? How likely is it? What measures ensure continuity and recovery? These questions reveal whether you're paying for necessary enablement or unnecessary insurance, and whether a maintenance plan or tailored plan is needed for your sites.

Conclusion

The traditional agency support model is fundamentally broken, built on incentives that reward your dependency rather than your success. But the alternative isn't just finding a "better" vendor—it's rethinking what support means entirely. The best relationships are built on enablement, transparency, and shared success metrics.

Whether you need a retainer at all depends on your specific situation, but one thing is certain: if your current vendor profits more when you have more problems, it's time for a change. Listen to the full episode for deeper insights into spotting red flags, structuring value-driven partnerships, and determining what level of support actually makes sense for your organization.