How Olo saved $300K and leveled up their HRIS platform with OutSail

About

Olo is a leading hospitality tech solution that empowers restaurants to increase orders, streamline operations, and make every guest feel like a regular. Since their founding in 2005, Olo has partnered with over 700 restaurant brands to reach 85 million connected guests across 85,000 locations.

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Challenge

Olo needed an HRIS platform that could keep up with their rapidly expanding headcount

Since onboarding their previous HRIS platform, Olo has more than doubled their team headcount — and now they have their eyes set on global expansion. While their old system served them well in scrappier days, its lack of customizations required more manual upkeep as they scaled. For Senior Manager of HRIS Hannah Stein, this meant it was high time for an upgrade.

To make the right selection, Hannah knew she needed a better grasp of the sprawling HR software space. But doing the in-depth research needed was an overwhelming task for her busy team.

So Hannah decided to look for an external partner who could objectively lay out every option. When Olo’s trusted benefits broker recommended OutSail, Hannah was excited to check it out. OutSail’s instant attentiveness to Olo’s needs and deep industry expertise made the choice a no-brainer.

“The sea of HRIS options is really overwhelming to navigate — especially if you want to avoid bias. We knew OutSail’s insider knowledge of the HR tech industry and zero-pressure approach would help us keep it real.”

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Solution

OutSail helped Olo simplify vendor analysis and handle sales calls with confidence

With OutSail at their side and a selection deadline set, Olo embarked on a speedy search for the best HRIS platform. To facilitate this process, OutSail created a customized shortlist of 12 vendors that broke down each option’s pricing, pros and cons, and match score based on Olo’s requirements.

After Hannah’s team reviewed their shortlist, OutSail instantly generated a Request for Proposal (RFP) that clearly defined the high-level business goals they hoped to achieve with their new platform. This document solicited straightforward proposals from four finalists, enabling Hannah’s team to easily compare their choices across three categories: pricing, value, and functionality.

“Reviewing each vendor with OutSail gave us so much more leverage in sales conversations,” says Hannah. “When you’re just one team with limited industry connections, it’s hard to advocate for yourself — but OutSail already works with every single vendor and knows all the questions to ask and red flags to identify.”

This deep dive also gave Hannah’s team the confidence to commit to a solution they might otherwise have written off. Although their winning platform was more expensive than others they’d considered, OutSail helped them see beyond biased competitor reviews and identify the platform’s scalability and exceptionally high ROI potential. What’s more, with OutSail’s guidance, they were even able to negotiate down their vendor’s initial quote to secure the most favorable payment terms.

“We needed to know where each vendor fell in terms of pricing, value, and functionality, and OutSail made it crystal clear. They saved our team countless hours of research and networking.”

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Results

Olo selected its best-fit vendor in just 90 days

Thanks to OutSail, Olo carefully assessed every HRIS possibility, cut costs, and implemented a truly bespoke platform in half the time it would’ve taken to DIY. Now, Hannah and her team have an HRIS foundation powerful enough to shore up their rapid growth.

The results speak for themselves:

• $300K savings over 3 years
• 90 days to run process
• 4 best-fit vendors identified
• 100+ targeted vendor questions prepared

Moving forward, Hannah is excited to experiment with the new platform’s premium and customizable options. As Olo accelerates toward the 1,000-employee milestone, she knows her team will have all the support they need.

“The OutSail team understood our needs to a tee. Picking a new HRIS was a huge investment for us, but they supported us throughout the entire process and made sure we found the perfect fit.”