The Sales Operations Guide to Evaluating Sales Tools

5 min read

All good sales operations leaders know that the first step to building out a smart tech stack is identifying areas in the sales process that need attention. Once you’ve identified those areas, then comes the fun part – choosing a shiny new sales tool. But once the initial excitement wears off, the task of evaluating sales tools can seem a little daunting. With so many vendors to choose from, each offering ‘the best money can buy’, even the most experienced sales ops leaders can become lost.

We wanted to put the fun back into evaluating sales tools, so we asked our community of sales operations leaders how they do it.

Brandon Bussey, Director of Revenue Operations, Lucid

For 2019, I’m looking at purchasing a sales enablement tool to evolve our tech stack and enable the sales reps. Rather than me doing a bunch of demos, I put together a team of sales leaders and reps and presented five categories (including enablement software, insight management, call recording etc) and we discussed which would be the most useful and chose a category. Then enablement and I surveyed the market and came up with who we think the top two to three players are for us and we had them come in and run demos with that same panel. We’re currently at the stage of doing the POC. Then I’ll sit down and find out what they thought. This is proving to be a much more impactful approach because the sales leaders and sales reps have more involvement. It doesn’t feel like Brandon from his glass castle is making decisions by himself. It’s their choice as much as mine.

I’ve seen a big impact with this approach compared to other projects I’ve seen or even done myself. We’ve failed with full transparency in the past and that’s sometimes because of tight deadlines for rolling out a process. The learning from this is giving ourselves enough time to bring sales leaders and reps up to speed as to why we’re doing it and getting them involved in the decision where possible.

A key ingredient for us is those front-line managers. If they’re bought in, the reps will buy in. The managers have garnered a lot of respect from their reps.

Read our interview with Brandon.

Rebecca Silverstein, Manager of Sales Operations, Smartling

First of all, you should consider at a really high-level what you need this tool to do. And then from there, breaking it down and saying, so that means that we definitely need X, we definitely need Y, we definitely need Z. And then look at the features and benefits on G2 Crowd or similar rating providers. But keep in mind you don’t want to just see the Best of the Best, you just need the best fit for you.

Then it’s about going through your criteria checklist and looking at all the vendors who have met that criteria.

Read our interview with Rebecca.

Jessie Schreiber, Director of Sales Operations, Program Management, Ibotta

I am actually starting an initiative to take one away – we’ll call it “tool A.” Tool A worked 5 years ago, but we have outgrown it. I am in the early stages of deprecating it and introducing a different tool, “Tool B” that has everything “Tool A” has, plus much better reporting functionality. Some people won’t be happy initially, but it’s only because it represents change, uncertainty and a few hours of extra work up front.

I will give you another specific example where we transitioned from Yesware (the Inbox point solution) to Outreach, which is a more fully baked sales engagement platform. If I had to go back, I probably would have re-signed for at least a year with Yesware.

We knew the team didn’t love Yesware – it was plain, simple, and we consistently experienced technical issues with the Chrome extension. But the key to that was, it was simple. So I had a sizable group of people across all teams, across all roles, and we went through a pretty deep-dive into vetting Outreach and their other competitors in the space.

I had created surveys, they evaluated, and I created a thorough competitive analysis that was reviewed by sales leadership. Outreach came on top but for a lot of the wrong reasons. That didn’t get discovered until after we tried to implement it and the complexity became apparent. Testers liked the user interface during the buying process but that shouldn’t have driven our decision. The product was built for SaaS companies that handle high volumes of prospecting and need all the bells and whistles and sequences. We don’t, we need something simple that provides specific value without keeping our teams from their actual selling activities.

I have learned some valuable lessons about what to look for, and what feedback does and does not matter. In some instances, I can objectively say that the way that people are using something is not how it was intended to be used.

“Tool A” is not meant to be used for someone’s personal task list. So if people come to me saying “I can’t do my job without it,” I hear them out, but am ready to explain exactly how “Tool B” is going to be a better version of that task list, plus more.  I prepare for those conversations ahead of time.

Read our interview with Jessie.

Kirsty Charlton, Head of Sales Operations, Signal AI

It starts with undertaking demos and making a shortlist. Decide on some KPIs and rigidly score each tool that way. Those KPIs could be ease of use, whether it integrates with Salesforce etc.

I can give you an example of a great buying and onboarding experience we had which ticked all the boxes.

We were looking at Outreach and the first positive sign was that they use their own tool. After every call we had with them, they sent us a personalised email. They laid everything out in steps and it meant that we moved down the sales funnel really easily. We were always given the right material at the right touch points. They also have a fantastic knowledge base with explainers.

Ultimately, we didn’t ever feel like we were being sold to. People love buying but hate being sold to, right?! They’ve got reps who’s job is purely to onboard people – they’re experts in the tool and are extremely helpful, available at anytime and always have the answer.

Read our interview with Kirsty.

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