OutSail Reviews & Provider Details

Outsail was an outstanding partner throughout our HRIS evaluation process. They helped us clearly define what we actually needed (not just what vendors were selling), guided us through identifying the best-fit solutions, pressure-tested our top HRIS contenders, and supported us through contract review with a sharp, unbiased lens.

Brett, the CEO, brings deep strategic insight and credibility—he’s clearly built the firm around real-world HR and operator experience, not theory. Logan, the Director of Advisory Services, was equally impressive: organized, pragmatic, and relentless about keeping the process focused, efficient, and aligned to our business goals. Brett also supported us in the final stages by translating complex HRIS tradeoffs into plain language and actionable decisions, saving us significant time and helping us avoid costly missteps.

If you’re navigating an HRIS selection and want a partner who’s independent, knowledgeable, and genuinely on your side, Outsail is absolutely worth it. Review collected by and hosted on G2.com.

We connected with OutSail to solve the problem of the current HRIS no longer meeting our needs and to evaluate a new solution. We were facing a complex HRIS evaluation with competing priorities, strong sales pressure from vendors, and real risk of choosing a system that wouldn’t scale with our business or culture. OutSail brought structure, independence, and expertise to the process. Helping us clarify our true requirements, objectively evaluate and compare platforms, and understand the real tradeoffs between options.

The benefit was a faster, more confident decision with far less risk. We cut through marketing noise and entered contract negotiations informed and prepared. Ultimately, OutSail helped us select an HRIS aligned to our operational needs and long-term strategy, not just what looked good in a demo. Review collected by and hosted on G2.com.

I would recommend OutSail Review collected by and hosted on G2.com.

Choosing a New HRIS/Payroll Provider Review collected by and hosted on G2.com.

With a background in HR consulting and HRIS implementations, I knew just how overwhelming it could be to select a new HRIS provider. I’d been the one creating complex spreadsheets comparing HRIS options, so when I heard about Outsail, I was genuinely intrigued.

Working with Outsail was a game-changer for my team. Their support was invaluable—they helped us quickly narrow down a shortlist of vendors that aligned with our unique needs, saving us tons of time and effort. They provided us with a document that was clear and comprehensive, breaking down each vendor's offerings and highlighting which would best fit an organization of our size and with our needs.

Brett, the founder, was there for us every step of the way, always ready with answers, insights, and guidance. His expertise made us feel confident and informed throughout the process.

Outsail’s industry knowledge and commitment to supporting buyers made a daunting process feel manageable. Their proposal analysis and negotiation guide were a huge help in securing the best deal. I’d recommend Outsail to any company choosing new HR software—they simplified the journey for us and I am so grateful! Review collected by and hosted on G2.com.

Once you determine your needs, start with OutSail before doing your own research on the options. Without a service like OutSail you could spend hours and hours looking into options (and feeling overwhelmed) without any direction or process for narrowing down. Review collected by and hosted on G2.com.

OutSail took all the HR tech solutions available on the marketplace (and there are A LOT of options!) and helped us narrow down based on our needs then provided a comprehensive overview of the options with unbiased reviews of each as well as metric-based evaluation tools to assess them ourselves. Without OutSail, I was overwhelmed by the options and biased by all the people selling their solutions. After using OutSail I felt confident we were making an informed choice. Review collected by and hosted on G2.com.

Our organization was looking for a more comprehensive and scalable HRIS platform. Brett was so easy to work with. He really listened to what was important to us to provide us with a short-list of vendors that were targeted to our current and future needs. He assisted through every step of the process, guided us through questions to ask during vendor demos, and helped us tremendously during our negotiation phase! His insight was exactly what we needed to not only find the vendor best suited for our organization, but to get the very best pricing possible. He was always quick to respond and had answers for every question we asked! Review collected by and hosted on G2.com.

With countless HRIS options on the market, it's easy to get overwhelmed by the daunting process of researching and evaluating different systems. OutSail made it a breeze - we had curated options presented in an easily digestible format, saving me countless hours of research and allowing me to jumpstart the project way faster than I would've been able to otherwise. Knowing that our shortlist had vendors specifically tailored to our company's size and was invaluable and meant we were evaluating solid options from the get-go. Thanks to OutSail, we identified and signed on with our new HRIS provider within weeks - not the months I was expected to have to dedicate to this project! Review collected by and hosted on G2.com.

If you have a concern or need in the HR technology space (whether ATS, Employee Engagement platform, HRIS or others), they are an absolutely excellent consultant to work with to understand your pain points and help you really hone in on what alternatives are available. Review collected by and hosted on G2.com.

We were having trouble with our current HRIS and our setup. We needed to consider a new solution to keep up with our accelerated volume and size. They were able to get us several vendor options while also providing great resources to draw comparisons and get a wholistic view of what the best HRIS solution looks like for you. Review collected by and hosted on G2.com.

Think through what criteria are important to your decision making in advance to help you get the best data as quickly as possible. Review collected by and hosted on G2.com.

We worked with OutSail to determine which HRIS made sense for our company as we scale from about 50 people to up to a few hundred. We had a lot of constraints including integrations with existing systems and nuances with our org structure and employee distribution. OutSail helped us find appropriate options and gave us meaning criteria and scoring to make the decision making easier, and then introducing us to the right teams at each company. Review collected by and hosted on G2.com.

Make the call! Get them involved in your HRIS search! Review collected by and hosted on G2.com.

Helped me select a new HRIS provider. I had 4 different ones I was evaluating and Brett at Outsail helped me narrow my choices to 2 and then Brett helped with price negotiation which got us the system we liked the most. Review collected by and hosted on G2.com.

I definitely recommend companies partnering with OutSail. The support and knowledge expertise that OutSail brought to our table will assist us in being succesful in our quick turnaround implementation. Review collected by and hosted on G2.com.

My company was in a very difficult position withour our current HRIS. We were struggling and not receiving the service we need to be successful. We made the decision to start the process to find a new system on a short timeframe. We could not have accomplished this huge lift without the assistance of OutSail and Brett! We were able to narrow our search to 3 top matches which in the end saved us countless hours of searching and viewing demos! Review collected by and hosted on G2.com.