TABLE OF CONTENTS
Edited & Reviewed
Why do 56% of organizations regret their tech purchase within just two years? Worse, that regret sets in before software implementation even begins.
Moreover, 67% of stakeholders sit outside IT, including those in finance, legal, operations, and security. As expected, misalignment and delays are common, and a slow or scattered approach can become a significant business risk.
Here’s all you need to know to avoid these issues and move towards a more efficient software procurement process.
TL;DR:
- Software procurement can either simplify operations or create years of tech and financial debt; it all depends on how you handle the process.
- This article walks you through 9 steps to get software procurement right.
- Before you look for tools, you must engage stakeholders, map future-state workflows, and conduct an audit of existing software.
- It’s equally important to examine integration skills, data handling practices, support models, and contract terms related to security and SLAs.
- Finally, monitor adoption, measure outcomes, and set regular checkpoints to revalidate vendor fit or renegotiate terms.
Step 1: Define software requirements through business objectives
Enterprise environments are inherently fragmented.
Marketing wants more automation; finance requests audit trails, and security teams require access control. Procurement teams must gather all of these inputs, but not as a departmental wishlist.
Instead, requirements for software (even hardware) should be structured by business use case and broader strategic objectives.
This means translating abstract feature requests into concrete operational needs. For example:
Replace ‘we need audit logs’ with ‘finance needs traceable records for quarterly reviews.’
Read More: 10 Steps to Optimize Your IT Procurement Process
Step 2: Audit your existing tech stack and procurement policies
Once your requirements are in place, account for what’s already in use before investing in new software.
We recommend examining all organizational tools, as well as any operating below the radar.
This is necessary to determine what is duplicative, outdated, underutilized, or non-compliant.
During the audit, map all existing applications by:
- Functionality and usage: List the business processes each tool supports, how heavily it's used, and by which teams.
- Integration and dependencies: Find tightly coupled tools. Are they pushing/pulling data across platforms, and if so, how?
- Licensing and Cost: Review the number of paid seats versus the number of seats in use, and verify for duplicate subscriptions.
- Security posture: The tools used must meet current compliance standards. Also, verify whether access controls and data policies remain valid.
Once the audit is complete, plan what to procure by analyzing your procurement policies. Also, check if your policies are still relevant.
This is also a good time to review whether your current procurement method relies on manual processes or outdated digital workflows.
In rare cases, it’s better to rewrite policy frameworks than to force every tool through a broken or outdated process.
Step 3: Involve stakeholders early in the process
PwC’s research finds that projects with effective stakeholder engagement are statistically more likely to succeed.
Yet in many enterprise environments, software procurement is still treated as an IT-only initiative until the final stages.
Here's who to involve to make procurement more collaborative:
- Business unit leaders who can validate how software maps to current and future workflows.
- Finance and accounts payable for processing payments, reviewing payment terms, and other financial aspects.
- Legal and compliance, to review data handling, auditability, and contract language.
- Security, and
- Support and operations for backend and user issues.
Bringing stakeholders in early avoids procurement-by-escalation, where a project is paused halfway through because the legal team finds an unacceptable clause or because the tool violates a data residency rule that never surfaced.
Here’s a Redditor sharing a practical example:
Via Reddit
Remember, this must not mean opening the gates to opinion overload. Establish clear decision-making frameworks with the right people, and:
- Schedule working sessions to gather needs and constraints.
- Create a decision-making matrix: who’s an approver, who’s a contributor, and who’s informed only.
- Share evaluation criteria so stakeholders understand what trade-offs are being considered.
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Getting software into the right hands shouldn’t be a messy, manual process. With Workwize, a global IT hardware lifecylce platform, software gets deployed alongside hardware from day one—no IT tickets, no delays. Workwize also pulls licenses back when someone leaves and gives teams a clear view of what’s being used. 
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Step 4: Conduct market research and create an approved vendor list
Once the requirements and stakeholder alignment are in place, shift your focus outward to market research.
Begin by understanding the landscape: the leading and emerging vendors, new technologies dominate, and preferred pricing models.
Before you even start looking at vendors, define your research objectives, such as:
- Typical vendor capabilities and limitations
- Regulatory or compliance factors
- Standard technical requirements and integrations
- Business structures and contract models
- Pricing benchmarks (“should-pay” pricing)
- Potential risks: financial, operational, and performance-related
A good method is to run peer interviews. Talk to industry counterparts who’ve made similar purchases and ask pre-scripted questions.
Check out this Redditor’s response to a thread on market research. In many ways, this person reflects what we feel:
Via Reddit
From there, your search area for potential vendors and potential suppliers widens.
- Use Gartner or Forrester to understand the market and established vendors.
- Read case studies from companies of similar size and complexity.
- Explore community forums like Reddit and G2 for real-world experiences.
- Request demos tailored to your actual workflows.
Now, narrow down your list methodically. Filter vendors by geographic coverage, capacity, financial health (using tools such as Dun & Bradstreet), and alignment with your specific requirements.
Towards the end, you’ll have a tiered, approved vendor list.
Step 5: Draft and issue a detailed RFP or RFI
Once you’ve got a list of vendors ready, send out a Request for Proposal (RFP) or Request for Information (RFI) to learn how well vendors can solve your specific problems.
Your RFP/RFI should be clear, technical, and precise. At a minimum, it should include:
- A short, contextual project overview
- Detailed requirements, broken into functional and non-functional sections
- Integration points, such as APIs, authentication layers, and data pipelines etc.
- Certifications like SOC 2, ISO 27001, encryption standards, and the like
- Implementation and support expectations
- Your evaluation framework
- Standardized submission format and deadlines
You can also include a pricing template so vendors return cost breakdowns in a consistent format.
Don't write your RFP in isolation; consult with other departments before issuing it, so their constraints are already factored in.
Via Reddit
Finally, give vendors enough time; at least 2–3 weeks for proper responses, as 20 percent of RFPs are left incomplete due to time constraints.
Procurement leaders should view this as a key step in the entire procurement lifecycle.
Step 6: Evaluate proposals for security, scalability, and ROI
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“You can't hold firewalls and intrusion detection systems accountable. You can only hold people accountable.” - Darryl White, BMO Financial Group |
At this stage, your shortlist is in place, but to select a vendor, you must assess how each proposal meets the demands of an enterprise-grade solution.
Start with security. Every vendor should be measured using a structured framework. The Cloud Security Alliance (CSA) CAIQ and NIST 800-53 are commonly used as benchmarking controls for access, encryption, auditability, and incident response. Vendors should provide evidence of compliance: SOC 2 Type II, ISO 27001, or FedRAMP if applicable.
Scalability comes next. Look at the system architecture and performance metrics under load. For ROI, conduct a full cost analysis to measure the total cost of ownership and identify potential cost savings.
Again, you don’t need to evaluate in isolation. Bring in finance to validate ROI assumptions and security teams to stress-test risk claims.
At the end of this process, you want a clear understanding of which vendor meets your specifications and which one can withstand the operational realities of your environment.
Related Read: Hardware Procurement Automation: All You Need to Know
Step 7: Evaluate legal terms, SLAs, and compliance clauses
Once technical and financial evaluations are complete, legal and compliance reviews come in. This is where risk management lives.
The first thing to conquer is the Master Services Agreement (MSA). Here, you focus on liability caps, indemnification, data ownership, termination clauses, and governing law.
Review the SLA next. Look for guarantees on uptime, response times for critical incidents, escalation paths, and penalties for missed targets. Don’t entertain vague language like “commercially reasonable efforts.”
This Reddit user puts advice in perspective:
Via Reddit
For compliance, the vendor must meet your industry’s regulatory requirements, typically HIPAA, GDPR, CCPA, PCI DSS, etc. Ask for documentation: data processing agreements (DPAs), audit logs, subprocessor lists, and retention policies.
Legal and security teams must collaborate during this phase. If even one clause raises suspicion, resolve it before moving forward.
Step 8: Plan implementation with IT, finance, and operations departments
Implementation takes a coordinated effort across systems, budgets, processes, and people. IT manages deployment and integrations, while finance tracks spending and validates forecasts.
When treated as IT’s job alone, deadlines slip, and adoption suffers.
Instead, form a cross-functional task force with clear roles, timelines, and shared accountability..
Step 9: Monitor adoption and conduct regular vendor reviews
Finally, once new software is live, you must track its use and whether it delivers the expected outcomes.
Quantifiable metrics, such as active users, usage depth, support tickets, and integration success, will indicate whether teams are bypassing the tool or relying on outdated systems.
Ultimately, never ignore post-purchase oversight, or there’s a real chance your expensive software will become shelfware.
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Workwize is an IT hardware lifecycle management platform that lets you procure IT hardware, manage, track, retrieve, and dispose of it globally.
Lepaya automated its IT processes with Workwize and saved $44 K per year. You can, too.
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