startup sales desk

How to Buy Sales Software

When I joined Abacus, I was the first business hire on a 5-person team. At the time we were trying to figure out how to structure the sales machine, the marketing machine, the support machine and almost everything else.

Thankfully, we live in a time where you can accomplish much more with the right technology in place. We were able to stay lean by adopting systems that helped us work smarter and faster. There’s a SaaS solution for almost everything.

One of the first things we wanted to do was make sure we had the right tool set, so we spent a lot of time evaluating solutions. After a bunch of hits and misses, we eventually came up with an approach for buying sales software.

Conduct an Internal Audit

Take some time to become familiar with the tools your team is using. It’s more than likely that reps have gone ahead and adopted new tools just to help their own individual workflows.

Whether those are tools such as Salesloft, Clearslide, or, knowing what is currently in place can help you shy away from software whose features may overlap with your existing tools. Most importantly, you need to get real feedback about what they like, dislike and need.

You’re likely trying to architect a workflow that solves for 15 different pieces, and your reps have probably independently solved for a few of them – now you can focus on the gaps.

Identify Your Needs

Before soliciting feedback from my team, I map out my ideal workflow for whatever the solution does. After collecting feedback, it’s easy to figure out where the misalignment is. It’s either going to be something where you have visible gaps, or it’ll be something where it’s tough for reps to stick to the right process and they skip steps.

Building a ranked list of your needs is a key step. There’s so much sales software out there that solves different and overlapping areas, so it’s important to understand your needs first to make sure you find the solutions that specifically target your focus areas.

I like to categorize my needs into two buckets:

  1. Productivity optimization
  2. Doing things “the right way” (ex: correctly storing leads in a CRM so you can efficiently recycle, assign and suppress against).

Now you can start to research and reach out to vendors you think could be a good fit.

Question Your Vendors

Sales reps know how they want to present their software – what features to hit on and what order to go through in their presentation.

Since reps are used to mechanically following their presentation plan, I like to start the demo by laying out everything I’ve discovered about my needs up to that point along with the things that I am looking to solve. It helps me ask the curve ball questions up front and also helps the rep better tailor the demo.

Asking the curve ball questions keeps them on their toes, and informs me of how their software solves my unique needs or whether I’m thinking about the process all wrong. I’ve definitely been coached into re-working my strategy a few times.

It’s also important to give the sales rep the time to go through all the features that could be relevant to you. It’s not always easy to understand a certain feature from the start but it’ll be something you want to keep reference of as your team scales and new things become relevant.

After a demo, here are some typical questions I hit on:

  • What does your typical buyer look like?
  • When your customers are successful, what features do they love?
    • What other tools are they using with this?
  • Why did you lose deals in the past?
  • What questions did you wish I asked?
  • What’s on the product roadmap?

I also love talking to other companies about what tools they’re using. It’s the most helpful gut check. Asking around, especially with peer companies that are about 12-18 months ahead of you, can help you understand what sales tools they used to use and what triggered changes.


I try to do demos and evaluations with at least three vendors (rule of 3’s). After that, it’s time for trials, the fun stuff.

I pick one or two people internally to test the software for a week and get their feedback. I’ll check in with them every day to get general feedback on how it’s going and then at the end of the week, really dive into what they liked and didn’t like about the software.

You will have already mapped out your ideal process in step 1, so you can do an audit of whether everyone is sticking to the plan.

During the trial, stay engaged with the sales rep – make sure what they said before holds water now. They may have said something during the demo that isn’t on point with how things actually works. Call them with any problems that may come up during the demo to make sure you’re getting the most out of the trial. I really value buying software from responsive teams that are able to make adjustments quickly.


After the trial process, there’s almost always a clear winner. You’ve already screened for budget, you’ve seen the features and how they work for you and now you’re ready to buy.

For the most part we don’t negotiate price because we jump for the month-to-month contracts instead of an annual deal. As an early-stage company, we love the flexibility. There’s also so much advancement in the market, that you want the optionality to review new vendors.

After The App Is Live

Always be screening. As mentioned, we like to go month-to-month because of how easy it is to switch if need be.

If people reach out to you for new software, it’s worth it to look at a demo (live or recorded). You never know, it could make your work more productive or solve a problem that has recently cropped up in your organization. It’s what we see with Abacus all the time.

It’s what we see with Abacus all the time. We talk to companies already using Expense Management tools, but once they look at what we do, it becomes an entirely new conversation that surfaces up opportunity. Constantly be open to new and better software.

Dev Anand

Dev Anand is the Strategy & Business Development Director at Squarspace. Squarespace empowers millions of dreamers, makers, and doers by providing them with the tools they need to bring their creative ideas to life. Dev was the Director of Sales at Abacus.