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Make Software Purchasing Painless

I want to make software purchasing painless for anyone reading this post. When I first broke into Business Systems, I had to pick up various non-technical skills. 

One of the top three was vendor management and procurement. I had yet to learn what I was doing and made every mistake in the book. It was excruciating.

Of the many things I love about my role is the ability to support every department. This means learning how they operate and what specialty software they use to get stuff done.

This has led me to sit in on countless sales cycles across multiple industries and verticals. I learned the rhythm of how these calls go and what I should be sharing but also listening for.

Combining these experiences with supporting sales organizations, you get to sit in a particular seat to understand what is happening in this weird dance called sales.

Often, buyers think it’s a complicated process. True, there are mechanisms in place to create asymmetry. But, I want to share with you how to make SaaS purchasing painless, and that first starts with knowing the process.

The Sales Process

There are tons of resources out there that go into deep detail about the sales process and what it is. Gartner provides overall guidance – I don’t buy into the Gartner Magic Quadrant, but they have other good content. Zapier goes into great detail about the process.

But, for our purposes, I will distill it down and potentially use non-standard terminology. So, sales folks, yes, some liberty has been taken for readability.

Why? Because in order to make things painless, we need to know what to expect.


If you’ve ever received a quirky LinkedIn message, email, or even the dreaded cold call, you’re officially a prospect. Someone thinks you are in the market for what they want to sell. Congratulations!

How did they get this idea? From lists they bought, data they’ve collected to build a profile, and a bunch of other magic that may appear on this blog someday.


This is where you talk to a Sales Development Representative (SDR) or equivalent.

Regardless if it’s a cold call or they’re responding to a lead form you’ve filled out, they are confirming information about you.

In addition to this confirmation, they determine if you are a fit for their product or service. They’ll ask you about your use case, the size of your company, and any other platforms you may have.

These determine what the next steps are.


This call may be combined into the pitch meeting. But this is where you meet your Account Executive, who will guide you through the rest of the process.

They’re building onto the qualification meeting and asking more probative questions. Here they may share bits and pieces of the product to gauge your interest.

They’ll also ask four usual questions: do you have a budget? What is the buying process, and where are you in the process. Are you looking at competitors?

The discovery phase is to determine how large a lift the sales process will be and to understand how to craft a tailor-made demo for you.


This is the core of the process. Here is where they share the product with you and the value their company brings.

You may see a sales manager on this call to lend extra support. Different faces may include an implementation manager or sales engineer.

The meeting cadence usually includes a few slides on the background of the product or company, a demo, questions, and the next steps.

Bring everyone who you think is vital to attend. They can ask questions here, and they should. It would be best if you also prepared them beforehand for the meeting on what to listen for and why you’re looking to purchase.


Where you’re presented with how much it’s going to cost you. 

Honestly, this is the most adrenaline-pumping part of the process. But, hold on, you don’t get to pricing first.

You will be sold on the product again for a few slides and then get the pricing. Then you’ll discuss your feelings about the pricing and the next steps.

Contract Execution

The fun part. DocuSign or something similar (always different to keep your boss on their toes) is sent and signed. 

Yay! You bought something. 

Enough said.

How To Make Purchasing Painless

How do you make the purchasing process painless? I have some good news and bad news. 

The biggest thing you can do requires no additional work. It just means knowing this is a cooperative process. 

The bad news is that you will have to do some work ahead of time to ensure everything runs smoothly.

Don’t Be A Jerk

These tips aren’t in any particular order, with the exception of this one.

Just be nice. The sales process is really a win-win for everyone when done correctly. It’s okay to be cordial.

Understand there are rhythms to meetings. It involves some small talk before business. It may mean repeated concepts or multiple meetings.

You don’t have to be a shrewd negotiator or start questioning everything from the beginning. 

There’s a process for a reason. It makes everything have a rhythm.

When you are cordial, it reduces pressure and increases the likelihood the seller will work with you on pricing.

Remember your relationship with the company exists post-sale. You want to avoid being flagged in their CRM as a demanding or difficult customer. 

Also, you may work with your AE again to buy additional SKUs or upgrade. They’ll remember.

Further, they can assist you in raising any support requests.

Know What You Are Wanting To Buy

This seems common sense. But you’d be surprised at how many folks make their discovery during the sales demo. 

They leverage the salesperson to tell them what they should be looking for and what they need. This is a seller’s favorite. They can craft a narrative. If the seller is good enough and the first, they’ve set a benchmark you can’t move from.

You’ll hear me scream requirements in order to understand what you want to buy, but this doesn’t mean a complicated process with many spreadsheets.

Know what problem you’re looking to solve. 

What is the problem, and why will software fix it. What features are around that you need? 

What is a deal breaker, a nice to have, and a that would be cool if? Please stick to your deal breakers. There’s a reason that they are that.

Also, do a bit of research in the space before you start talking to vendors. Know the competitors, and understand what the landscape looks like. 

When you come to the table with knowledge about the landscape and product, you can ask deeper questions. 

Know Your Procurement Process

Getting to the dotted line and being blocked by other departments will frustrate you. 

So, before taking a spin around the block with vendors, do a little internal discovery. Figure out who is on your procurement team and what the process is.

Typically this team comprises Finance, IT, Legal, Security, and sometimes a project management office. They are your partners and can make the process painless.

They will have guidance for things they are looking for if the product is on a restricted list or maybe your organization has a product in place already.

This is a good time to determine if you need to submit formal requests, budget addendums, or what documents you need during the process. They will also give you an idea of how long the process takes.

I recommend engaging early, before any meetings with vendors. This will keep the process flexible, and you don’t have to worry about delays later.

This also helps you with the vendor. Let them know at the beginning if there will be heavy redlines or if they need security documents that need extra work, or if your procurement process takes a long time.

Know How Much You Can Afford

Nothing is worse than getting to the end of the process and then negotiating internally. 

It’s frustrating for everyone. 

Your email is blowing up from the rep following up, and you want an excellent product that will solve all your problems.

This is why knowing your procurement process is essential.

Knowing what you can afford is vital to the entire process. There isn’t much point in investing time into demos and research if there won’t be a budget for the product.

Before engaging finance (or your leadership), it would be best to do some competitive research to determine what the price may be first. 

This does two things: it lets you prepare for what the price may be and gets a baseline for your finance team ahead of time.

How do you do this?

Surf their site for pricing, try to find clients, look at postings on forums, or hint around it with an SDR or AE. Also, ask internally, someone may have purchased the product at a prior company.

The more you know ahead of time helps you level set. But keep in mind that pricing on a website may be the max price. There may be negotiation room.

It’s okay to negotiate.

Don’t accept the first offer. It’s like paying sticker on the car lot.

Companies will never want to make the lowest amount that’s possible. 

Most often, this is the best guess based on your company size, past deals they’ve had that look like you, and a bit of intel about your budget.

If it seems wildly out of line with what you’re expecting, take the time to discuss it with your team. Let the seller know that “it’s a bit higher than I thought, and we’ll need to debrief internally.”

Chat with your team, figure out what your counter is, and pitch it back. This is where you see your sales rep work between their management and operations teams.

Don’t be unrealistic here. Use your best judgment based on your research and use that as a benchmark. Don’t want this pressure? Consider a company like Vendr to provide all of these details for you.

Don’t be a jerk and try to renegotiate if they meet you at your number. Yes, you probably had more room to go down, but it’s called good faith.

Having someone else to defer to on this is excellent. Usually, the CFO or other executive will advise if they think the price is reasonable and can inform budget.

Sales teams are incentive driven and have pressure to meet quotas. 

This is where being flexible comes into play. You’ll see better discounts if you have time to buy at the end of a month, quarter, or fiscal year.

If you’re briefing your procurement team ahead of time and can move quickly, you can get a discount for closing fast. You may get pressure to commit to a date, but know the seller wants this deal. You can usually extend this date.

Multiyear sales will also garner discounts. A caution here, as you will want to have the ability to negotiate an opt-out after the first year or truly know this is the platform for you. Nothing is worse than picking a bad product and still paying for it.

You should have set a baseline price discovered on competitive research before. This is what you’re willing to accept. Don’t go above this. Knowing what you’re ready to accept will make life easier. It also sets your benchmark ahead of time.

A caveat: If a company tells you they don’t negotiate, trust, and then verify it. Companies like Slack will sell you the price on the website, no different. Differences here are if you’re in the nonprofit or government sectors.

It’s okay to share

You don’t have to keep all the information to yourself. Please share it with the vendor. 

Are you working with competitors, or are you switching from one? Do you have this approved in your budget?

Let them know if you’re stuck internally or have to punt a project. This rapport builds over time. 

You never know if your sales contact goes to another company; they’ll remember how it was working with you. 

I’ve worked with some of the same sellers at multiple companies and sometimes bought different products from them. Your network really does help.

Make Software Purchasing Painless Conclusion

There is a ton more that I can share with you on the process of procuring software, but I hope this is a good primer on how to make it easier.

The more you engage in these discussions, the easier they are. But you’re also not alone in the process. 

There are communities out there to support you in your journey, and there are probably great resources internally at your organization as well.

The best advice I have is: we’re all people at the end of the day. Don’t feel intimidated. 

Do you have any tips on making the buying process easier? I would love to hear them.

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