7 Commandments for a Regret-Free SaaS Purchase

Selecting the right software product for your business is a complex and critical task. The process involves multiple steps that, if carefully understood and planned in advance, can make your purchase quick, easy, and provide long-term benefits. Unfortunately, companies often let the software vendor dictate the buying process rather than taking control and steering the decision-making. This can lead to choices that are heavily influenced by vendors and may not fully align with your original business needs.

Coming from a SaaS organization and selling SaaS products for the past 10 years, I have observed and understood companies that make the right choices with ease and documented the same. Below are the 7 commandments that you should follow to make the software buying process safe and regret-free. These steps will empower you to navigate the software selection process with confidence, authority, and predictability, ensuring that you become the Moses of your organization.

1 — You Shall Do Your Homework

Thoroughly Document and Prioritize the Problems

The first step is to thoroughly prepare before you start shopping. I know you’re eager to onboard a product and finally resolve that persistent issue you’ve been dealing with, but remember: an excited buyer with a fat wallet is every sales rep’s dream. Before you even begin searching for vendors, make sure you document all your problems clearly and prioritize them using a MoSCoW list. While the primary problem might be obvious, there are often edge cases, legacy use cases, special considerations, and regional variations that the software should be capable of handling. These details might only come up later from team members with questions like, “By the way, how do I do this in your software?” So, talk to every persona who will be using the product and gather complete requirements from them. Your purchase will be used by several personas in the organization; an executive’s expectations will be completely different from an operational user’s. So, understand the requirements from the whole spectrum and document the same.

Get Internal Buy-In

Ensure you’ve had enough conversations with internal team members about this purchase. Talk to your peers about their past product purchase experiences, and get their suggestions. Make sure the Procurement, IT, Security, Compliance, and Engineering teams are on board with this purchase. There will be overlaps, redundancies, and dependencies with other departments. These should be addressed and understood early on before you start shopping.

Get Your Case and Budget Approved

Build your case, circulate it internally to all key stakeholders, and secure the necessary approval and budget (in writing). While the exact budget can be finalized later, ensure that the company is willing and able to set aside funds for this problem. Additionally, try to offload some of your regular responsibilities so you have the time to focus on the purchase. Juggling your day-to-day activities with this task will reduce your ability to make the right decision, leading to rushed choices as the deadline approaches.

Pro Tip: Most sales teams in SaaS companies use an internal lead qualification technique to gauge the likelihood of a purchase. The most popular method is BANT, which assesses if the buyer has Budget, Authority, Need, and Timeline to make the purchase. A simple hack is to perform a BANT analysis on yourself. This self-assessment will give you a good indication of how successful your purchase is likely to be.

2 — You Shall Request for Proposal

When it comes to purchasing software, the natural dynamic between you as the buyer and the vendors as sellers might make you feel like you don’t need to put in much effort. This perception is often reinforced by sales reps who treat you like royalty. However, the reality is that even after spending money, you’ll need to work hard to make this purchase successful. Enterprise software isn’t like scrolling through Instagram reels — there’s no instant gratification; mistakes made now will show their symptoms a year down the line, and ROI is hard to calculate. You need to approach the entire process, from the initial decision to the go-live phase, as a well-planned project. It’s easy to lose focus and feel safe after selecting a vendor, expecting their team to handle everything. But for long-term success, you must have a clear plan in place, starting from the RFP stage to go-live and execute the plan diligently.

Prepare a Plan that Starts from Request for Proposal to Go-Live

Create a comprehensive RFP (Request for Proposal) and share it with potential vendors. A well-crafted RFP simplifies the shortlisting process for both you and the vendors. After publishing the RFP, carefully review the responses from each vendor, and ensure you give them ample time to fully understand your requirements and provide a thoughtful response. It’s important to include every aspect of the solution in your RFP — not just your business problem and cost considerations. Be sure to thoroughly address other critical factors, such as documentation, training, security, compliance, data location, availability, upgrades, and backward compatibility in your RFP.

Keep in mind that there may be delays from the vendors’ side, especially if you’re working with multiple vendors simultaneously. To keep the process on track, plan each activity carefully and maintain a sense of positive urgency in your communications with vendors to ensure timely responses.

3 — You Shall Shortlist the Vendors

After receiving and validating responses from the RFP, take time to review product feedback on G2, understand the company culture, company financials and once you are confident in the product, request a demo that covers the most important use cases outlined in your RFP. The product demo is the decisive moment for buyers, so it’s crucial to take the demo carefully and evaluate the product in action (avoid recorded demos). For better judgment, involve colleagues who can offer different perspectives during the demo and get their views. Be transparent about what you liked and didn’t like, and ensure the demo focuses on the specific pain points you provided to the vendors in advance.

After the demos and validation, maintain a scorecard to evaluate and compare the various vendors you’re considering. Once you’re satisfied with the demo and reviews, request access to a trial system. Spend ample time exploring the system to assess how self-service capable the system is and to understand its true capabilities in terms of getting started without external assistance.

After completing your final stage evaluation, take the time to make your decision not just based on features and cost but also on the overall value the software will provide. The value of a software product is a combination of several factors, including its ability to meet your immediate needs, address future requirements, the level of service provided, its self-service capabilities, and whether the product roadmap aligns with both your current and future needs. Consider all of these aspects carefully before making your final choice.

Pro Tip: One of the easiest ways to judge a product’s capabilities apart from demos is by reading their documentation. The documentation pages are mostly designed for signed customers and cannot lie about what is possible and what is not (there are no sales agents here). So, read the product’s documentation and also browse through their support forum. Look at the tickets raised, the responses given, and how the community is engaged as a whole. This gives you an unbiased perspective of the product and the services associated with it.

4 — You Shall Review the Contracts and SoWs

After shortlisting vendors, the next critical step is to thoroughly review the Contracts and Statements of Work (SoWs) provided by the vendors. These documents outline the terms of your engagement, the deliverables, timelines, and most importantly, the legal obligations of both parties.

Understand the Contract Terms

Before signing anything, ensure you understand the contract’s key details, such as the length of the agreement, pricing structures, renewal terms, and any penalties for early termination. Pay close attention to clauses related to price increases, data ownership, and service level agreements (SLAs).

Get Legal and Financial Teams Involved

This is the point where your legal and financial teams should get involved. Have your legal department review the contract for any red flags or ambiguous terms that could pose a risk to your business. Also, if there are any aspects of the engagement you want to be completely certain about, try to get that added to the contract. This will legally bind the vendor to deliver on this rather than just promising to do so next.

Get and Review a Scope of Work (SoW)

The Statement of Work is where the rubber meets the road. It details the specific services the vendor will provide, including the implementation process, support levels, and post-go-live services. Ensure that the SoW is as detailed as possible and that it aligns with your RFP and any promises made during the sales process. Any ambiguity here could lead to misunderstandings and unmet expectations later on. Vendors are often willing to make concessions to close the deal, especially if they know you’re considering multiple options. So, any such negotiations made should reflect in the SoW and Contracts.

Pro Tip: Ensure there’s an exit strategy in the contract. A well-defined exit clause can save you from long-term commitments if the software doesn’t meet your expectations after deployment. This could include provisions for data export, transition assistance, or a clearly defined offboarding process.

5 — Sign with a Vendor

Sign the contract, make the payments, and select the partner. From this stage onwards, it is important to build the relationship with the vendor like a partner, not just a buyer and seller. For a successful implementation, you need a true partner who can work with you. So, build your relationship and shift your focus to planning the implementation. This is where the real fun begins, and having a solid plan in place is crucial to avoid delays and ensure a smooth onboarding of the new system.

Create a Detailed Project Plan

Work closely with the vendor. Ensure that all stakeholders are on the same page and that there’s a clear communication plan in place. Ensure you clearly explain the rationale behind your decisions. Everyone should know what to expect, what the milestones are, and who is responsible for each part of the process. Clearly define the timeline, and track progress regularly to ensure the project stays on course.

Pro Tip: It’s essential to have regular meetings and status updates with your vendor. These should include key stakeholders from both sides. This will ensure that any potential issues are caught early and addressed before they become major roadblocks.

6 — Test, Validate, Train and Go-Live

Before going live, it’s crucial to thoroughly test the system to ensure it meets your expectations and that it’s functioning as expected.

Test the System

Start by running extensive tests, including unit testing, integration testing, and user acceptance testing (UAT). This will help you catch any issues before they become larger problems. Make sure to include all stakeholders in the testing process, and ensure that the system meets the business needs as documented in your initial MoSCoW list.

Validate the System

Validation involves checking whether the software meets the needs of your business. This means running the software through a series of real-world scenarios to ensure that it performs as expected. Make sure that the software integrates well with your existing systems and that it can handle the data and workflows specific to your business.

Train Your Team

Finally, make sure that your team is fully trained on the new system. This includes not just the basics of using the software, but also how to handle any potential issues that might arise. Ensure that your team is comfortable with the software before going live.

Go-Live

Going live is the final step in the process. It’s important to plan this carefully and ensure that everything is in place before you flip the switch.

Plan the Go-Live Process Plan the go-live process carefully. This includes setting a go-live date, ensuring that all stakeholders are available, and that there’s a clear plan in place for handling any issues that might arise. Ensure that the vendor is also on hand to assist with any issues that might arise.

Pro Tip: If possible attach an expansion, upgrade or a referral to a successful go live with your vendor. This will give vendors enough incentive to ensure that the implementation and onboarding is successful and fast.

7 — You shall calculate ROI

Monitor the System After going live, it’s important to monitor the system closely to ensure that it’s functioning as expected. This includes monitoring system performance, checking for any issues, and ensuring that the system is being used as intended. There would be an initial period of frustration, anger, resistance with you and your team, this is common and expected whenever a major change happens and users are asked to change their behavior.

Calculate the ROI

Review the ROI after a few months of using the new software, evaluate whether it’s delivering the expected return on investment. This includes not just financial metrics but also improvements in efficiency, user satisfaction, and other business outcomes.

Inform the Internal Sponsors

After the successful go-live and ROI calculation make sure you inform all internal teams of the success and circulate the data about the enhanced efficiency and ROI of the investment.This is important for you to secure budget approval for renewal of the product.

Pro Tip: Every software org knows that it is easier to retain existing customers than finding new ones. They also know that you are locked in with them for now as well. So if you feel you are not being heard after going live, don’t hesitate to throw in the churn scare once in a while to get the attention that you deserve.

In Conclusion

Remember, the key to a regret-free SaaS purchase lies in preparation, collaboration, and vigilance. Thoroughly understanding your business needs, engaging your internal teams, and maintaining control over the buying process will empower you to make a decision that you’ll stand by, not just today but in the years to come. The time and effort invested upfront will pay dividends, ensuring that the software you select truly supports your business growth and success.

In the end, a successful SaaS purchase isn’t just about choosing the right product — it’s about building a strong partnership with your vendor, executing a well-planned implementation, and continuously monitoring the solution’s performance to ensure it evolves with your needs. By approaching this process with the right mindset and strategy, you can make your software investment one that drives tangible results and leaves you with zero regrets.