4 Steps to Getting Ahead in Today’s Complex Software Buying Cycles

Why does software buying feel so complicated now?

Gone are the days when a single buyer or procurement team could make a software decision in isolation. Today, purchasing software is a highly scrutinized, multi-stakeholder process involving finance, IT, security, procurement, and department-specific leaders. Why? Because:

1. There’s No Longer a Sole Expert: With an overwhelming number of vendors and tools in the market, it’s impossible for procurement teams to be experts across all categories.
2. Increased Risk Exposure: Beyond just cost, companies must now consider security risks, compliance requirements, and tech stack compatibility.
3. Opaque Pricing: Software pricing is often inconsistent, making evaluation more time-consuming and complex.

The result? Longer buying cycles, surprise renewals, and budget overruns. So how do we move from reactive buying to a strategic, controlled process that puts buyers in the drivers seat?

Step 1: Gain Full Spend Visibility & Centralize Data

The foundation of any strong procurement strategy is visibility. Without it, companies are constantly blindsided by unexpected purchases and missed renewal opportunities.

A common mistake is trying to establish a process first and assume visibility will follow. But it should be the other way around—visibility must come first. 

• It aligns procurement initiatives with company growth goals.
• It helps identify cost-saving opportunities, such as eliminating duplicate subscriptions.
• It prevents expensive mistakes, like missing an opt-out date on a high-value contract.

One company built an entire negotiation strategy for Slack, leveraging price benchmark data. However, they discovered too late that their opt-out date had passed—losing a potential $200K in savings that could have been reinvested elsewhere.

A common mistake is trying to establish a process first and assume visibility will follow. But it should be the other way around—visibility must come first. 

This is why visibility must include a single source of truth for spend data. By centralizing spend data across all stakeholders—procurement, finance, IT, and department heads—companies can identify duplication, track commitments versus actual usage, and make more informed decisions. Without this foundation, even the best negotiation strategy can fail before it begins.

Step 2: Implement Smarter Governance (Without Slowing Down Innovation)

A common misconception is that more approvals lead to better decisions. In reality, excessive complexity slows teams down, frustrates stakeholders, and leads to “shadow IT”—where teams buy their own tools to avoid red tape.

Instead, good governance should focus on:

• Strategic checkpoints: A single, knowledgeable stakeholder reviewing smaller purchases for red flags.
• Real-time data: Leveraging price benchmarks to prioritize focus. If your Asana renewal is priced optimally but LinkedIn is overpriced, direct your negotiation efforts accordingly.
• Automation: Manual processes kill momentum. Set up renewal alerts, automate supplier document collection, and streamline workflows so stakeholders don’t have to chase down approvals.

One procurement leader faced this challenge when their engineering team needed a new development tool urgently. Balancing that urgency with security and budget considerations, they used real-time data to fast-track the approval. Instead of blocking innovation with cumbersome processes, they streamlined approvals for low-risk tools while focusing scrutiny on higher-risk or high-cost purchases.

Step 3: Maximize Buying Power by Consolidating & Optimizing Spend

Many companies waste money because different departments independently purchase similar software. Without a unified source of truth, it’s easy to miss consolidation opportunities. This fragmentation weakens negotiating power and leads to redundant contracts.

To fix this:

• Start with Step 1 and centralize expense data and contracts to quickly identify duplicate spending.
• Empower department heads with visibility into company-wide spend so they can make smarter purchasing decisions.
• Enforce better spend decisions through workflow automation, ensuring purchases go through proper channels.

A finance leader we worked with was shocked to discover that three different departments had separate contracts with the same analytics vendor. By consolidating them into a single enterprise agreement, they unlocked volume discounts, eliminated redundancy, and significantly improved vendor relationships. This approach not only reduced costs but also streamlined internal processes for future renewals.

By consolidating them into a single enterprise agreement, they unlocked volume discounts, eliminated redundancy, and significantly improved vendor relationships.

Step 4: Use Varied Data to Drive Smarter Software Investment Decisions

Many procurement teams think price benchmarking is the answer to smarter software purchases. While benchmarks are valuable, they are just one piece of the puzzle. Before looking outward, companies must first analyze their own spend data (seeing a trend on why you need to start with getting your data all in one place?).

• Historical spend: What did you commit to, and how does that compare to actual usage? One company purchasing Loom added licenses throughout the year without realizing they exceeded their original commitment. Because of this, they missed out on volume discounts.
• Usage data: Are you actually using what you’re paying for? If only 75% of your team is using Monday.com, maybe not everyone needs a license.
• Price benchmarks: Then, layer on price benchmarks and ask yourself Are you overpaying relative to peers? Understanding market pricing helps prioritize negotiations.
• Negotiation intelligence: Last, but most important, knowing the best price isn’t enough—you need vendor-specific tactics to secure that price. 

Without this layered data approach, you risk leaving money on the table. 

A well-executed procurement strategy isn’t just about cutting costs—it’s about ensuring every dollar spent drives value. Companies can take control of their software purchases and maximize ROI, without slowing down innovation. A little upfront legwork goes a long way in avoiding overspending and costly inefficiencies.