Don’t Buy Like the Fortune 500: A Better Buying Model for Small Businesses

Avoid the Fortune 500 trap—discover how SMBs can make smarter HR tech choices tailored to their size, budget, and growth goals for long-term success.

Brett Ungashick
OutSail HRIS Advisor
April 23, 2025

Small and mid-sized businesses (SMBs) often look up to Fortune 500 companies for inspiration, especially when it comes to building their technology stack. It’s easy to assume that what works for the biggest and most successful organizations will work for you. But when it comes to buying HR technology, copying the enterprise playbook can be a costly mistake. Here’s why—and how SMBs can build a smarter, right-sized approach.

The Fortune 500 Trap

Fortune 500 companies are often seen as the gold standard in business operations, including their choices in HR technology. Many SMBs, eager to grow and professionalize, try to emulate these large organizations by purchasing the same software platforms and tools. On the surface, this seems logical: if a solution works for a global giant, it must be robust and future-proof.

However, the reality is that enterprise software stacks are built for a very different scale, budget, and set of needs. For SMBs, adopting these tools can backfire, leading to wasted resources, frustrated teams, and stalled growth. The key is to recognize the unique context of your business and adopt a buying model that’s tailored to your size and goals.

Why Enterprise Buying Models Don’t Fit SMBs

Enterprise software isn’t one-size-fits-all. What suits large corporations often burdens small to medium-sized businesses (SMBs) with complexity, high costs, and unused features. SMBs need lean, flexible tools—not bloated enterprise systems.

Here’s why Enterprise Buying Models Don’t Fit SMBs.

1) Different Budgets

Enterprise tools are expensive—not just in licensing fees, but in implementation, customization, and ongoing support. Fortune 500s can afford dedicated internal teams to manage these systems and negotiate long-term contracts. SMBs, by contrast, must be much more cost-conscious and agile. Complex enterprise solutions can quickly overwhelm a small team’s capacity and budget.

2) Different Org Structures

Large companies have layered hierarchies, specialized departments, and complex workflows. Their HR tech stacks reflect this complexity, with modules for every conceivable function. SMBs, on the other hand, rely on leaner teams where people wear multiple hats. They need tools that prioritize speed, simplicity, and flexibility, not sprawling feature sets designed for thousands of users.

3) Different Priorities

Fortune 500s optimize for scale, compliance, and risk management. Their HR tech is designed to handle global payroll, complex compliance requirements, and large data volumes. SMBs need to focus on ease of use, fast onboarding, and tools that solve immediate pain points. Flexibility and time to value matter far more than long-term scalability at this stage.

Common Mistakes Small Businesses Make When Copying Big Co’s

What works for giants can sink the small. Too often, small businesses mimic enterprise decisions without considering scale, resources, or priorities. But copying big companies can lead to wasted budgets, underused tools, and operational drag.

Here are the most common mistakes SMBs make when trying to follow in Fortune 500 footsteps.

1) Over-prioritizing Features Over Fit

Enterprise tools often come with every bell and whistle. But for a small team, this can be overwhelming. Many features go unused, yet still require maintenance, training, and support. SMBs end up paying for complexity they don’t need, which can create confusion and slow adoption.

2) Undervaluing Service and Support

Fortune 500s have internal HRIS teams to manage their software, troubleshoot issues, and liaise with vendors. SMBs rarely have this luxury. They need vendors who offer hands-on support and act as true partners, not just software providers. Choosing a tool without considering the quality of customer service can lead to headaches down the line.

3) Choosing by Brand Name, Not Business Need

Big logos create FOMO (fear of missing out), but what works for a multinational may not be a good fit for your business processes or team capacity. SMBs should focus on solutions that fit their workflow, culture, and growth trajectory, not just the most recognizable brand.

4) Underestimating the Cost of Complexity

A tool that requires 12 weeks of training and 10 hours per week to maintain is not viable for a three-person HR team. The hidden costs of complexity—lost productivity, frustrated employees, and stalled projects—can outweigh any perceived benefits.

A Better Buying Model for SMBs

Small and mid-sized businesses (SMBs) face unique challenges and opportunities when selecting HR technology. Rather than replicating the enterprise approach, SMBs should adopt a buying model that aligns with their size, resources, and growth trajectory. Here’s a proven, step-by-step approach for SMBs looking to build a world-class HR foundation—without the bloat.

1. Start with the Problem, Not the Platform

Before evaluating software, clarify your most pressing HR challenges. Are manual time-tracking processes causing payroll errors? Is onboarding inconsistent, leading to poor first impressions? Are compliance requirements becoming overwhelming?

  • Pinpoint Specific Pain Points: List the top three HR issues that consume the most time or cause the most frustration. For example, you might struggle with tracking employee absences, managing compliance documentation, or keeping up with recruitment.
  • Engage Stakeholders: Involve HR staff, managers, and even employees in identifying these pain points. Their perspectives will highlight real-world problems that software must solve.
  • Set Measurable Goals: Define what success looks like—such as reducing onboarding time by 50%, eliminating manual data entry, or automating compliance reminders.

This problem-first approach ensures you invest in solutions that address your business’s real needs, rather than being seduced by flashy features that don’t add value.

2. Buy for the Next 2-3 Years, Not the Next Decade

It’s tempting to choose a platform that claims to “scale forever,” but SMBs often experience rapid and unpredictable change.

  • Prioritize Short- to Mid-Term Needs: Focus on tools that will serve you well over the next two to three years. Your business may double in size, pivot, or restructure—so flexibility is more valuable than hypothetical long-term scalability.
  • Scalability Without Overcommitment: Look for software with modular features or tiered pricing, allowing you to add functionality as you grow, without paying for unused capacity upfront.
  • Avoid Over-Engineering: Don’t be pressured into buying enterprise-grade systems with features you won’t use. Instead, select a solution that can adapt to your evolving needs but remains simple and cost-effective in the present.

By focusing on the near future, you avoid locking yourself into expensive, complex systems that may not fit your business in a few years.

3. Prioritize Ease of Use and Time-to-Value

For SMBs, time and resources are precious. The HR system you choose should be intuitive, quick to implement, and easy for everyone to use.

  • User Experience Matters: Select platforms known for logical navigation, clear interfaces, and minimal training requirements. A system that’s easy to use will see higher adoption and less resistance from your team.
  • Rapid Implementation: Ask vendors about typical rollout times. Many SMB-focused HR solutions can be deployed in days or weeks, not months.
  • Immediate Productivity: Look for features like employee self-service, automated workflows, and pre-built templates that help your team become productive quickly.
  • Customer Reviews: Check independent reviews to see how real users rate the platform’s usability and how quickly they saw benefits.

A system that’s too complex or requires extensive training will slow your team down and erode ROI.

4. Vet Service Levels as Hard as the Tech

For SMBs, vendor support is just as important as product features.

  • Onboarding and Training: Ask about the onboarding process—will the vendor provide hands-on setup assistance, training sessions, and resources tailored to small teams?
  • Ongoing Support: Evaluate the quality and responsiveness of customer support. Is help available via chat, phone, or email? What are typical response times?
  • Peer Feedback: Read reviews and case studies from other SMBs to gauge satisfaction with vendor support. Top-rated vendors for SMBs are often praised for their customer service and willingness to help clients with limited in-house HR expertise.
  • Customer Success Resources: Look for vendors who assign a dedicated account manager or success specialist, ensuring you always have a point of contact.

A vendor that feels like an extension of your team can make a significant difference, especially when HR resources are stretched thin.

5. Focus on Integration and Flexibility

SMBs typically rely on a mix of tools for payroll, benefits, scheduling, and more. Your HR software should connect seamlessly with these systems.

  • Integration Capabilities: Ask about pre-built integrations with popular payroll, accounting, and time-tracking tools. Seamless integration reduces manual data entry, minimizes errors, and streamlines workflows.
  • Open APIs and Customization: If you have unique needs, look for platforms that offer open APIs or customizable connectors so you can build tailored integrations as your business evolves.
  • Avoid Data Silos: Centralizing HR data in one system improves accuracy and reporting, while disconnected systems can create inefficiencies and compliance risks.
  • Adaptability: Choose software that can be easily reconfigured as your processes change, whether you add new benefits, update compliance requirements, or expand your team.

Integrated, flexible systems future-proof your HR operations and keep your business agile.

Practical Steps for SMB HR Tech Buying

  • Map your current HR processes. Identify bottlenecks, manual tasks, and compliance risks.
  • Engage your team. Involve end users—such as HR staff, managers, and employees—in the selection process to ensure buy-in and adoption.
  • Set clear goals and metrics. Define what success looks like: reduced admin time, faster onboarding, improved compliance, etc.
  • Shortlist vendors based on fit, not just features. Look for tools that solve your specific problems and are designed for small to medium-sized businesses (SMBs).
  • Ask for demos and trials. Test usability, support responsiveness, and integration with your current systems.
  • Check references and reviews. Learn from other SMBs’ experiences—what worked, what didn’t, and why.
  • Negotiate for flexibility. Look for monthly contracts or tiered pricing that lets you scale up or down as needed.
  • Plan for implementation and training. Make sure your vendor offers onboarding support and resources tailored to small teams.

Closing: Small Business, Smart Choices

You don’t need to buy like the Fortune 500 to build a world-class HR foundation. In fact, trying to do so can set you back. With a right-sized strategy and modern, SMB-focused tools, you can punch above your weight, delivering efficiency, compliance, and a great employee experience without the bloat.

Be deliberate. Ask tough questions. Build for your team, not someone else’s org chart. The best HR tech for your business is the one that fits your unique needs, culture, and growth stage—not just the one with the biggest brand or the most features.

By focusing on your real challenges, prioritizing usability and support, and selecting flexible and scalable solutions, you’ll set your business up for sustainable success.

“As a smaller enterprise, you’re simply easier to do business with. Suppliers can offer more aggressive pricing terms because the costs of doing business with you are lower, and the chance of maintaining a longer relationship with you are higher… So don’t assume that smaller volumes equate to inferior pricing. You have more leverage than you may think.”

Don’t fall into the Fortune 500 trap. Build smarter, not bigger. Your business—and your people—will thank you.

Reports
2025 HRIS 
Landscape Report
Read OutSail's 2025 HRIS Report with write-ups on 30+ leading vendors
Thank you! You can download your report at this link
Oops! Something went wrong while submitting the form.
Expert Support
Brett Ungashick
OutSail HRIS Advisor
Accelerate your HRIS selection process with free support
Thank you! Our team will reach out to you shortly
Oops! Something went wrong while submitting the form.
Newsletter
The HR Tech Download
Stay on the industry's cutting edge with our popular newsletter
Thank you! You will receive the next HR Tech Download newsletter
Oops! Something went wrong while submitting the form.
HR Consultants
Challenges go beyond technology?
Download our "State of HR  Outsourcing" whitepaper. Discover trends, strategies & costs within the HR consulting world
Thank you! You can download your report at this link
Oops! Something went wrong while submitting the form.

Meet the Author

Brett Ungashick
OutSail HRIS Advisor
Brett Ungashick, the friendly face behind OutSail, started his career at LinkedIn, selling HR software. This experience sparked an idea, leading him to create OutSail in 2018. Based in Denver, OutSail simplifies the HR software selection process, and Brett's hands-on approach has already helped over 1,000 companies, including SalesLoft, Hudl and DoorDash. He's a go-to guy for all things HR Tech, supporting companies in every industry and across 20+ countries. When he's not demystifying HR tech, you'll find Brett enjoying a round of golf or skiing down Colorado's slopes, always happy to chat about work or play.

Subscribe to the HR Tech Download

Don't miss out on the latest HR Tech trends. Subscribe now to stay updated
By subscribing you agree to our Privacy Policy.
Thank you! You are now subscribed to the HR Tech Download!
Oops! Something went wrong while submitting the form.