5 questions to ask when buying software in a bear market

Madeleine Work
August 11, 2022
min to read

5 questions to ask when buying software in a bear market

Madeleine Work
August 11, 2022
min to read

I don’t usually share images of myself online, but here’s real footage of myself checking out the most recent marketing technology landscape

This is just to say that shiny object syndrome is real. There are a gazillion articles written about it: here, here, and here.

In normal times, shiny object syndrome is just a distraction (and a bane to ops teams everywhere). But when the future of the economy is uncertain, it can be detrimental to your business.

Source: Marketoonist

So how do you cut through the noise and build a stack that actually increases productivity and generates revenue? 

So glad you asked.

How to buy software in 5 questions

One thing you don’t want to do is buy tech willy-nilly. 

That’s why we consulted tech stack experts — including consultants at leading agencies like CloudKettle and SaaScend — for their top tips on building your tech stack, without being distracted by shiny tools.

1. Do you need it? Like… really, really need it? 

Is this solving a real pain you’re having? Or is a savvy salesperson just painting you a beautiful picture? 

To make sure you’re not just swooning, open a new doc and start writing. 

In that doc, clearly state:

  • The problem you’re having
  • How you expect this tool will solve the problem
  • Why this tool will solve the problem better than competitors 
  • How you will measure success 

At Chili Piper, we make decisions about tech (and everything else) using something called a decision memo. 

If you’re having a hard time getting started on this doc, check out our article “How to buy business software without bias” to see how we do it. We even included an example and template that you can copy.
 

-Dan Stratton, Partner at CloudKettle

2. Is it a top priority? 

Inefficiencies that can be fixed with technology are a dime a dozen. 

As you’re solving these inefficiencies with technology, you need to start with the highest priority item. This is even more true in a bear market when budgets are tight, and revenue is dropping.

Craig Jordan, CEO and Founder of SaaScend, prioritizes his tech buying decisions based on four criteria:

  1. Revenue-Driving: Anything that actively drives revenue, or gives time back to people driving revenue (e.g. sales reps, SDRs, etc.) is top priority. 
  2. Better Decision Making: Being able to make objective decisions allows organizations to be more nimble and more effective
  3. Time Savings: Your people should be focused on doing their jobs, not wasting their talents on mindless, repetitive tasks that can be automated. 
  4. Proactive Investment: Buy tools that you’ll be able to grow into. It’s better to have something you can grow into than to be reactive to problems that crop up.

Always, always, always start with tools that will drive revenue — because if you implement them correctly, you’ll end up making more money than you spend. 

For example, Chili Piper helps you connect prospects to sales immediately after they book a meeting — doubling your inbound conversions. More sales meetings = more revenue.


3. Do you have the budget?

This one is kind of a “duh.” But a good reminder for those in the back. 

👏 If 👏 you 👏 don’t 👏 have 👏 budget, 👏 don’t 👏 waste 👏 anyone’s 👏 time.👏

4.  Do you have the right people?

Every new tool needs a champion. 

That champion will be responsible for implementing the tool. Training your team. Setting up integrations with your existing stack. And checking in with your team to measure adoption. 

Don’t just buy something and throw it over the fence. That’s when tools fail. 

-Craig Jordan, CEO and Founder of SaaScend

5. How will you measure success?

When you’re buying a tool, you need to know: 

  • Your expected outcome
  • The metrics you’ll use to measure success

For example, if you’re considering buying Chili Piper’s Form Concierge, you might write something like this: 

Expected Outcome: We’ll increase the number of sales meetings booked and decrease the number of no-shows.

Metrics to measure: 

When it comes time for renewal, you can revisit these metrics to see if outcomes equaled your expectations.

What’s next?

If you haven’t read the first blog in our series, check it out here: How to buy business software, without bias.

Then, it’s time to find your community.

While this checklist is a great starting point, you’ll also want to get some first-hand advice from your peers before you purchase any tech. 
To do that, you’ve got to be part of the amazing RevOps communities out there. Here are some of our fave communities that you should absolutely join:

Finally, if you haven’t implemented Chili Piper, what are you waiting for? At the very least you should schedule a demo to see what all the hype is about.

I don’t usually share images of myself online, but here’s real footage of myself checking out the most recent marketing technology landscape

This is just to say that shiny object syndrome is real. There are a gazillion articles written about it: here, here, and here.

In normal times, shiny object syndrome is just a distraction (and a bane to ops teams everywhere). But when the future of the economy is uncertain, it can be detrimental to your business.

Source: Marketoonist

So how do you cut through the noise and build a stack that actually increases productivity and generates revenue? 

So glad you asked.

How to buy software in 5 questions

One thing you don’t want to do is buy tech willy-nilly. 

That’s why we consulted tech stack experts — including consultants at leading agencies like CloudKettle and SaaScend — for their top tips on building your tech stack, without being distracted by shiny tools.

1. Do you need it? Like… really, really need it? 

Is this solving a real pain you’re having? Or is a savvy salesperson just painting you a beautiful picture? 

To make sure you’re not just swooning, open a new doc and start writing. 

In that doc, clearly state:

  • The problem you’re having
  • How you expect this tool will solve the problem
  • Why this tool will solve the problem better than competitors 
  • How you will measure success 

At Chili Piper, we make decisions about tech (and everything else) using something called a decision memo. 

If you’re having a hard time getting started on this doc, check out our article “How to buy business software without bias” to see how we do it. We even included an example and template that you can copy.
 

-Dan Stratton, Partner at CloudKettle

2. Is it a top priority? 

Inefficiencies that can be fixed with technology are a dime a dozen. 

As you’re solving these inefficiencies with technology, you need to start with the highest priority item. This is even more true in a bear market when budgets are tight, and revenue is dropping.

Craig Jordan, CEO and Founder of SaaScend, prioritizes his tech buying decisions based on four criteria:

  1. Revenue-Driving: Anything that actively drives revenue, or gives time back to people driving revenue (e.g. sales reps, SDRs, etc.) is top priority. 
  2. Better Decision Making: Being able to make objective decisions allows organizations to be more nimble and more effective
  3. Time Savings: Your people should be focused on doing their jobs, not wasting their talents on mindless, repetitive tasks that can be automated. 
  4. Proactive Investment: Buy tools that you’ll be able to grow into. It’s better to have something you can grow into than to be reactive to problems that crop up.

Always, always, always start with tools that will drive revenue — because if you implement them correctly, you’ll end up making more money than you spend. 

For example, Chili Piper helps you connect prospects to sales immediately after they book a meeting — doubling your inbound conversions. More sales meetings = more revenue.


3. Do you have the budget?

This one is kind of a “duh.” But a good reminder for those in the back. 

👏 If 👏 you 👏 don’t 👏 have 👏 budget, 👏 don’t 👏 waste 👏 anyone’s 👏 time.👏

4.  Do you have the right people?

Every new tool needs a champion. 

That champion will be responsible for implementing the tool. Training your team. Setting up integrations with your existing stack. And checking in with your team to measure adoption. 

Don’t just buy something and throw it over the fence. That’s when tools fail. 

-Craig Jordan, CEO and Founder of SaaScend

5. How will you measure success?

When you’re buying a tool, you need to know: 

  • Your expected outcome
  • The metrics you’ll use to measure success

For example, if you’re considering buying Chili Piper’s Form Concierge, you might write something like this: 

Expected Outcome: We’ll increase the number of sales meetings booked and decrease the number of no-shows.

Metrics to measure: 

When it comes time for renewal, you can revisit these metrics to see if outcomes equaled your expectations.

What’s next?

If you haven’t read the first blog in our series, check it out here: How to buy business software, without bias.

Then, it’s time to find your community.

While this checklist is a great starting point, you’ll also want to get some first-hand advice from your peers before you purchase any tech. 
To do that, you’ve got to be part of the amazing RevOps communities out there. Here are some of our fave communities that you should absolutely join:

Finally, if you haven’t implemented Chili Piper, what are you waiting for? At the very least you should schedule a demo to see what all the hype is about.

Madeleine Work

Madeleine Work is a Content Marketing Manager at Chili Piper. She loves learning new things and making discoveries — and then sharing her learnings with others. When she's not typing away at her laptop, you'll probably find her running, hiking, or off on an adventure somewhere. Connect with Madeleine on LinkedIn.

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