OutSail helps companies research, evaluate, and select the right HR software- at no cost.
We act as an independent advisor, guiding HR and People leaders through requirements building, vendor shortlisting, demo orchestration, proposal analysis and negotiations.
We combine expert-led guidance with proprietary technology to cut through noise, surface the best-fit systems, and ensure you make a confident, well-informed decision.
We’ve supported thousands of organizations across industries, including organizations like DoorDash, Hims & Hers and Ramp.
Our HR Tech broker model allows us to deliver our advisory services at no cost to clients while remaining independent in our recommendations.
If you're a fractional CPO or HR leader navigating a new system decision, OutSail brings structure, expertise, and leverage- without adding cost or bias to the process.
"Working with Carl at OutSail was a game changer. The OutSail process made it much easier to identify several vendor options and clearly compare their strengths, weaknesses, and pricing. Their tools and reports surfaced insights we would not have uncovered on our own and helped us save a significant amount of time. This process was invaluable in keeping the executive team aligned and confident in both the approach and the final decision. Thank you!"
OutSail partners with Fractional People leaders as an extension of their team, bringing structure and expertise to HR tech evaluations.
Every engagement starts with a 30-minute kickoff to align on goals, timelines, and requirements.
From there, we quickly move into intake and shortlisting—delivering a curated set of best-fit vendors within a day.
We then collaborate to refine the shortlist, coordinate introductions to the right vendor reps, and run a structured demo process using OutSail’s tools.
Starting with OutSail (rather than going directly to vendors) ensures a more efficient process and unlocks better pricing, terms, and overall outcomes.
Your current HR or payroll system worked when you were smaller, but it’s now creating more problems than it solves. Reporting is limited, processes are manual, and it doesn’t support your complexity. OutSail helps you identify a system that can scale with your business and reduce operational headaches.
You’re ready to move off your PEO and bring HR, payroll, and benefits in-house. This transition can be complex, and choosing the right system is critical. OutSail guides you through vendor selection, helps avoid common pitfalls, and ensures you set up the right long-term infrastructure.
Your team is growing internationally, but your current system can’t handle multiple countries, currencies, or compliance requirements. OutSail helps you evaluate global-ready platforms and partners so you can confidently support employees wherever they’re located
HR and payroll tasks are taking too much time due to manual work, disconnected systems, or poor user experience. OutSail helps you find solutions that automate workflows, improve usability, and create a better experience for both your team and employees.
