HRTech Interview with Kevin Hollingshead

Kevin, we’re delighted to have you at HRTechCube. Could you start by sharing your professional journey and how it led you to your current role as Head of Partnerships at Check?
Good to meet! I started my career in finance, working as an analyst at a small fund in LA. Those years cemented my love for numbers and helped me establish a data-driven approach to my work very early on. I also knew on a personal level that I wanted to drive real-world solutions that would actually improve people’s lives. And that’s how I transitioned into Tech, where new companies were popping up, seemingly daily, that were promising to revolutionize this or transform that. Over the better part of the last decade, I’ve held various GTM leadership positions at Stripe, Apollo, and CultureAnalytics, spanning sales marketing and advisory roles. I’m currently Head of Partnerships at Check, where I drive our growth initiatives and forge strategic partnerships.

Can you give us an overview of Check’s platform and explain how it supports companies in building, launching, and scaling a payroll business?
a. Legacy payroll is broken. Every week, countless are wasted on trying to run payroll. Large, existing payroll providers often innovate through acquisition, leaving employers today with no choice but to use cobbled-together tools built for someone else. Other service providers split their focus or don’t have the experience that Check has earned since creating this category over five years ago.
b. Check’s payroll infrastructure is designed to be robust enough for public enterprises to rely on and approachable enough to be the de facto choice for startups. It’s one thing to build a payroll product. It’s an entirely different thing to build a lasting payroll business. Powerful APIs and clear documentation are table stakes. Empowering platforms with products and services, they can leverage to ensure payroll growth is what makes Check unique and what makes our partners some of the fastest-growing payroll businesses. With Embedded Setup and Embedded Support, we’ve productized what has historically been a laborious and high-friction experience for employers and a growth blocker for our partners.

How does Check’s intuitive API and the Components feature enable flexible and customizable payroll solutions for businesses?
a. Imagine a world in which running payroll means a quick glance at the numbers and hitting submit, taking a minute tops out of your Friday, allowing you to focus on what truly matters: your business. Imagine a world in which payroll is tailored to each industry and its particularities. Imagine a world in which payroll isn’t painful.
b. Instead of a one-size-fits-none approach, Check’s API is designed to be frontend-agnostic, enabling partners to build bespoke payroll solutions that cater to the unique requirements of different industries, such as restaurants and construction businesses. This flexibility ensures that payroll processes are streamlined, seamless, and efficient, allowing businesses to focus on their core activities while Check handles the complexities of tax calculations, filings, money movement, and compliance.

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