How Smart Teams Are Finding The Right Software

Information Overload

The process of buying software has become a nightmare for many HR teams. What should be an exciting opportunity to upgrade systems and simplify workflows, has instead become a daunting task.


The explosion of new HR technologies has led to a lot of innovation, but it’s also made it nearly impossible for HR professionals to keep a pulse on what services are out there, and which ones are a good fit for their team.



“The process of researching software is really tough,” said Julie Goldstein, People Operations Manager at Dynamic Yield. “One of the biggest challenges is where do you start? I’ll go to Google, but Google is tricky because there are so many paid ads. You don’t know which services are good and which are just paying to be there.”


Online review and comparison tools have become more popular in recent years, but those sites still leave HR buyers wanting more.


“There are review sites out there, but when I see a thousands 5-star reviews for BambooHR, I wonder “Are those reviews real? Are these only the happy customers? Are those companies my size?” said Alanna McCowen, HR Manager at Eggplant.


Not only is it difficult to trust the information out there, it’s also very time-consuming to obtain useful information from software companies. Most sales reps require a 45-minute conversation before disclosing basic information, like pricing.


“I’d tried doing research on my own,” said McCowen. “I’d tried sitting on demo, after demo, after demo. It was really time consuming and it wasn’t working. We ended up investing in a performance tool that we never used, so that was a very costly mistake.”


“Another pain point is those initial calls with those sales reps. They can be very aggressive with their follow-up,” added Goldstein.


With how overwhelming the technology landscape has become, many HR teams are forced to settle for less than ideal solutions. Rather than deal with a lengthy research process, teams are buying software they’ve used at a previous company, buying what their neighbor down the street is using, or vowing to deal with the problem next quarter.


A True Partner

Looking at this messy environment, the OutSail team saw an opportunity. Thousands of people are working on behalf of the companies selling software. But no one is working on behalf of the people buying software.


Launched in early 2018, OutSail is pioneering a new business model, one that charges the software companies and stays free for HR teams.


“The big draw for OutSail was that we don’t have to pay for your services,” said Goldstein.  “We’re a start-up and all of our costs have to be justified, so anytime there’s a free service that can deliver major value, that’s a huge win.”


The major value she was describing was OutSail’s vendor broker services. Early adopters within HR have started to make OutSail their first stop in a buying process. HR teams simply reach out to their OutSail advisor and describe the solution they’re looking for. Within a few days, their advisor sends over a detailed report of the best-fit technologies.



“I’m the only HR person in the US, so I always have a million balls in the air. Doing research and sitting on 45 minute calls just isn’t an option for me,” said McCowen. “With OutSail, I’d have a 10-15 minute call and, a few days later, I’d get a PDF with everything I needed. It was quick, easy and as painless as possible.”


“OutSail gave us the basic knowledge of what these platforms do, and that saved us hours of not having to meet with vendors that weren’t a good fit,” said Goldstein.


Beyond saving HR teams time and money, HR buyers have enjoyed working with someone who is a true partner.


Julie Goldstein wanted to provide a unique wellness offering to her employees, but she didn’t know if the service existed. She approached the OutSail team who hadn’t searched for this type of solution before.


“It was really refreshing that they didn’t tell me, “We only work with these five providers,” said Goldstein. “When I mentioned what we were looking for, they told us, “We don’t really know if that exists, but let me see what’s out there.”


Thankfully, the OutSail team was able to find what Goldstein was looking for and the wellness program is being rolled out in early 2019.


Simplifying the Future

It’s a great time to be in HR. Companies are starting embrace the importance of attracting and retaining talent, HR teams are becoming key stakeholders in strategic planning and technological innovation is continuing to allow HR teams to take on more transformational tasks.


“HR has been behind the technology curve for a while, but you can tell that HR is now stepping into the forefront,” said Laura Martinez, CHRO at JAMS. “I was at the HR Tech conference and so many people see the future, but don’t know how to handle it.”


Having a trusted technology expert in their corner is allowing HR teams to embrace this new era with open arms.


“I’ve implemented tons of software in my career. OutSail is making the buying process so much simpler,” said Anthony Kogan. “My only complaint is that it wasn’t around sooner.”



Get in touch with an OutSail advisor

And see how enjoyable the software buying experience can be