How to select the right business software for your startup

Sam Rosen, the co-founder of coworking-space subscription startup Deskpass, is intimately familiar with this challenge. With six full-time employees and roughly a dozen contractors, Deskpass requires a suite of software that is financially reasonable, can scale with the company, and frees up employees’ time so they can deliver the best human experience to their users.

Rosen is a self-diagnosed “software junkie” who has test-driven a host of business software options over the company’s near-decade of existence. Here are the lessons he’s learned about choosing business software for your team as it grows.

1. Fully understand your team’s needs

“Ask your team if they like what they’re using now, and understand what they’re using it for,” Rosen says. “Start there, and pick a solution that’s extensible.”

Consider diversifying the types of tools at their disposal, too. One size rarely fits all, and if you pick one all-inclusive business software solution from the beginning, any gaps are bound to become more of an issue as you scale.

“Different parts of your company will use the tools [you select] in different ways,” Rosen says. “You should ask: Should we all use the same tool? If we are using the same tool, does this work enough for everybody that they can use it appropriately and it’s not a stretch?”

Above all, you’re going to need your team to actually use the software product. They don’t have to be enthusiastic about it from the get-go, but it has to do enough for their day-to-day work that they’ll want to use it.

“If your team isn’t on board, it’s just a waste of your time and money,” says Rosen. “Picking something that your team can buy in to is almost as important as picking the right solution [for the business].”

2. Be realistic about your budget

The most expensive business software option might be an aspirational buy to prepare your company for the day it scales into corporate enterprise territory. But right now, that would likely be a massive drain on your resources and ability to stay agile.

“Figure out what your actual budget is. Don’t pay for something you don’t necessarily need,” Rosen says. Deskpass initially tried more robust software options like HubSpot and Marketo, but the streamlined Autopilot was more affordable for a small outfit and featured the option to scale up when the business grew.

Money isn’t the only budget you need to consider, either—so is time. “Factor in how long it’ll take to transition over, for people to adopt it,” Rosen suggests. “You have to consider the whole cost of all of the factors combined, not just the $200 a month the software costs.”

He adds, “There’s no holy grail. Every tool has drawbacks and advantages, so you have to pick what’s right for your team. Otherwise it drains your funds but also your political capital and your relationships, not to mention the time you could otherwise be spending building an awesome product.”

3. Always test-drive before doing a full migration

Pilot testing is a major factor in choosing new business software. “Don’t dive 100% in without testing it,” Rosen says. “We tend to try new tools in little experiments, because our business is pretty reliant on [them].”

Additionally, Rosen explains, “It wouldn’t ever be as simple as ‘Hey, now we’re using Google Chat’ or ‘Now we’re using Asana.’ Anything we choose will be a pretty big migration for how we communicate and prioritize, so we need to see [with a smaller test group] if we’re going to like it.”

4. Get business software that automates the least human parts of the job

Software shouldn’t be a replacement for human interaction. Quite the contrary—it should be used to minimize the robotic tasks cluttering up your people’s time and maximize their ability to engage meaningfully with one another and with your customers. For Deskpass, that means using automation apps like ProfitWell. It runs in the background throughout the day gathering business metrics data.

“The big win comes when I can spend five minutes in a day looking at data that otherwise would have cost a lot of my time and energy manually aggregating and reporting,” Rosen says. The key is to select “tools to replace things that I don’t need to be doing.”

Remember, some things can’t be solved with business software

“There’s no software substitute for human creativity and relationships,” Rosen points out. “Empathy is such an important characteristic in running a successful company and being a good manager. No matter how many tools and charts and graphs and spreadsheets you have, there’s nothing like high-fidelity communication: just getting on the phone and talking to people.”