The “White Hell Jigsaw Puzzle” might be the hardest puzzle ever made.

Its face is solid white, so there’s no picture to guide you. The pieces are so tiny, it takes precision placement to get it right. And at 2,000 pieces, one reviewer resorted to writing some code to solve it. For the impatient (or sane): turn back now.

If you’re in charge of building a tech stack for your sales team, you’ve got a puzzle like that on your hands. There’s no master template to help you map your tools. There are so many options to choose from, it’s hard knowing where to start, and what goes next. 

When things go right, the pieces seem to fall into place. But when you have a solution that just doesn’t fit, the whole thing starts to fall apart. 

Here are six signs your sales tech isn’t coming together, and how to find the pieces that really fit.

1) No one is using your tools

Adoption is a tough nut to crack at the best of times. If your tools aren’t making your reps’ lives easier or giving them useful insight into their work, it’s that much harder.


First, figure out why your reps aren’t on board. Are they struggling to understand a game-changing benefit, or does that benefit even actually change the game? If it’s the former, it’s time for a new adoption strategy. If it’s the latter, it’s time to reevaluate that tool.

2) It confuses your reps

Do your sales tools overlap? 61% of salespeople say between 1 and 5 of their tools are redundant. The result: reps aren’t sure which ones to use for which tasks, or where the best information lives.


Your tech stack isn’t a one-and-done solution. It demands regular attention to new tools as they become available, along with changes in old ones. Take a look at what you’re using today, flag overlaps, and work to reduce them. 

3) It didn’t solve your problem

Sometimes, tech is the answer – but in other cases, it can actually make the symptoms worse, or create new ones. If you’re light on leads, a tool that brings in low-quality prospects might fill up your pipeline today, but it won’t do you much good tomorrow.


Before you throw technology at a problem, assess the root cause, beyond the symptoms. You might find you brought in the wrong tool, or that a tool wasn’t needed at all. Sometimes all it takes is a change in process or procedure.

4) There’s too much training

If your tech stack takes an intense amount of training to get right, you can bet it’s not easy for reps to use in practice. With average SDR tenure sitting at about 1.4 years, the time they spend onboarding adds up, too.


The easier your tools are to use, the easier they are to learn. So when you’re evaluating your tech options, put value and usability for your reps front and centre. Don’t forget to look for integrations that streamline your processes so they’re easier to understand and execute, too.

5) Your team’s actually less effective, not more

The dreaded sales disablement trap: when our heartfelt efforts to make our reps more productive backfires. Despite our best intentions, three in four sales reps say increased sales support led to an increase in job complexity, and translated to a 12% lower conversion rate.


More isn’t always more. That doesn’t mean taking an axe to your tech stack, but rather listening to your team to figure out what’s draining their precious minutes, and whether there’s an opportunity to automate time-wasting tasks for them.

6) Reps can’t find what they’re looking for

Reps spend nearly a third of their day looking for content – and creating it when they can’t find what they’re searching for. The average search for information results in nada almost half the time. No wonder 52% of reps label looking for information as a top time-waster.


This one’s a pinch of tech and a dash of culture. Unifying your company’s information (including your reps’ dark knowledge) is the first half of the equation, whether it’s through a central repository or a platform that brings your existing systems together through one point of entry. The second half: instilling a culture where sharing is the norm to make sure that information is available when others need it in the first place.


Like the White Hell Jigsaw Puzzle, there’s no final picture to show you the way… but that doesn’t mean building a sales tech stack needs to be the world’s hardest puzzle. Your reps, their struggles, and the reasons they’re struggling are the best guides you could ask for. 


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