Rosterly reclaims 18 hours a week by putting its security posture in the open with Cairnwell

Helping teams hire the people they actually need

Rosterly is on a mission to make hiring legible — helping teams source, evaluate and onboard people without losing the thread. More than 3,100 companies run their hiring on the platform, from twelve-person studios to hospital networks.

Over the last three years Rosterly found real traction upmarket, and enterprise buyers arrive with a different set of expectations. The company already serves more than 900 enterprise customers, and that momentum keeps building. Those buyers care deeply about how their candidate data is handled, and they expect their vendors to hold themselves to the same bar they hold themselves to.

The Deal Desk team at Rosterly owns the job of making it easy for a prospect to say yes. That means finding a better way to answer security questionnaires and to share security documentation with prospective customers — without turning every deal into a research project.

Getting security answers in front of buyers earlier

As Rosterly grew, the team noticed that prospects wanted to do their own research before ever meeting a salesperson. They didn't want to sit through three calls in order to get a basic reading on Rosterly's security posture.

“By the time a prospect reaches us, they've already done most of their homework. We wanted the security answers to be part of that homework, not a gate at the end of it.”

As deals moved toward signature, buyers would send security questionnaires to confirm that Rosterly's posture met their standards. The formats varied wildly — spreadsheets, web forms, customer portals — but the questions underneath were nearly identical. In practice that meant sellers handed every questionnaire to the security team, who answered them one at a time, by hand. It was slow, and it usually took two or three rounds of follow-up.

“Prospects were talking to our privacy and security engineers very late in the cycle, and that step was often what delayed the signature. Our team spent whole afternoons on calls answering the same eleven questions,” says Rosterly.

It became clear that Rosterly needed a public destination where prospects and customers could do their own diligence. An internal wiki worked for a while, but it grew stale the moment the security program matured past it.

Autofilled questionnaires and a Trust Portal anyone can read

With Cairnwell's Questionnaire Autofill, Rosterly built an aggregated answer library drawn from its own security documentation and from every questionnaire the team had already completed. The security team now pulls from that library to respond to inbound requests, both inside Cairnwell and on third-party portals through the browser extension.

Alongside that, Rosterly took the proactive route and launched a public Trust Portal that centralises its compliance posture, security controls, privacy practices, subprocessors and more. Prospects and customers can review all of it in one place without booking time with anyone at Rosterly. Existing customers subscribe to the page and get a note whenever a document is refreshed.

What prospects and customers see when they visit Rosterly's Trust Portal

“The Trust Portal makes it straightforward to show customers that we're keeping pace with every change and revision in the regulations that apply to them.”

Rosterly also wired the Trust Portal into its CRM, so the team gets a signal the moment a prospect requests security documents. Sellers walk into the next meeting already knowing which topics the buyer cares about.

Shorter reviews, faster signatures

Since adopting Questionnaire Autofill and the Trust Portal, Rosterly has seen consistent gains in time saved. The team estimates the portal alone gives back a little over 18 hours a week.

Prospects are also moving through the process faster. In one deal, Rosterly cut several steps out of the cycle entirely: when the buyer's security team asked to schedule a review call, the seller simply put a link to the Trust Portal in the calendar invite.

After reading it, the prospect decided the call wasn't necessary and moved to signature. “That fast-tracked the deal and saved us an afternoon, because we never had to have the security conversation at all,” says Rosterly. All told, the Trust Portal helped accelerate more than $427,000 of contract value in the first year.