How OutSail Is Simplifying Software Buying

Last week, I was onboarding an HR team when their VP asked me a simple question: "Where did the idea for OutSail come from?"

Her inquiry was genuine. She loved that we were addressing some of the most infuriating things about working with software vendors - the nonstop outreach, the hidden information, the wasted meetings - and she was curious how we knew so much about these pain points.

I gulped like I was giving a confession, "Well... I used to be that annoying person in your inbox."

I began my career selling software to HR teams. It didn't take long for me to realize that the experience wasn't working for either side.

"Clearly no one in your shoes likes being constantly barraged by cold outreach," I told her, "and truth be told, few salespeople enjoy how transactional and automated sales has become."

"If the vendor-buyer relationship were to get more personal and more transparent," I explained "then someone was going to have to work on behalf of the buyers. And they should probably do it at no-cost to the HR teams."

That was the initial outline for OutSail: Work on behalf of HR teams, at no cost, to make vendor relations simpler.

Since then, we've gotten more specific about how exactly we do that. These are the five most popular ways:

1.) Consultative Intake

Today, companies are asking their HR teams to run leaner and leaner. As you get stretched thin, the daily to-do's can make it difficult to keep sight of strategic objectives.

With OutSail, each partnership starts with a 10,000 foot view. Helping our partners find the right solution requires more than just confirming it does X task and integrates with Y. For HR to be a true business partner, we need to take into account the state of the team, your strategic vision and how that intersects with the business's trajectory.

2.) Peel Back the Curtain

Among the HR teams we work with, a constant frustration is wasted meetings. Vendor outreach lands you on a vaguely interesting website, but as you dig around there’s never any pricing details, case studies or videos showcasing the platform.

Rather than hop on a 45 minute call only to find out it’s a bad fit within 3 minutes, HR teams working with OutSail receive detailed reports that cut through the sales-speak and show what the vendor actually provides, what it costs and what others are saying about it.

3.) Work On Your Timeline (Only Shorter)

Oftentimes a vendor who has got your attention, will do their best to convince you that, "Now is the absolutely essential time to start the buying process." This is their quota speaking.

You know your team's timeline better than anyone else, so we're always standing by on-call when the time comes. Within a week of our partners saying, "We're ready to start our HRIS search", we create reports on the best fitting vendors, go over the options with them and schedule calls with their preferred choices.

4.) Pitch Internally

Once our partners have determined which solution they like best, we help them make sure they get what they need.

Our partners can show the breadth of their research by using our side-by-side solution reports. We'll also help partners find other HR peers who are currently using the solution. We've even helped partners craft an ROI story for execs!

5.) Keep It Free (and Unbiased)

That's right - we do everything mentioned in points 1-4 at absolutely no-cost to the HR teams we work with. And you're probably wondering how that's possible (with a bit of skepticism). Here's how:

The way OutSail makes money is by charging every software vendor a flat referral fee each time we make an introduction. This fee is the same for all vendors (big, small, ATS, HRIS, etc.) so that we can stay unbiased. And the software companies have been happy to pay it, because they can get in touch with great teams without having to send thousands of cold messages.

Oftentimes our vendor partners will suggest that we join their pre-built referral programs because we can make more money that way. But we've stubbornly stuck to our flat fee, so that we can honor our commitment to being an unbiased matchmaker.

Get in touch with an OutSail advisor

And see how enjoyable the software buying experience can be