HRTech Interview with Kevin Hollingshead, Head of Partnerships at Check

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.

What role does the user-friendly customer management dashboard, Console, play in enhancing the overall experience for Check’s clients?
Check is built so that our partners don’t need to be payroll experts, hire huge teams with deep expertise, find engineers who can replicate the tooling of legacy providers, etc. No, our purpose is to enable modern payroll providers with the most robust yet lean path to delivering payroll to the businesses they support. Console, in short, is our prebuilt partner-facing control center where non-experts can manage the payroll product for all of their customers, which will help them gain deeper visibility into their payroll business. It provides a clear outlook both on high-level items such as companies and employees on their platform and more granular details like individual payrolls, benefits, and deductions.

Check works with category-leading platforms such as Housecall Pro, Homebase, and Wave. How do these partnerships enhance the payroll services provided by Check?
This is the beauty of Check and really our core claim. We tackle the undifferentiated work of tax calcs, money movement, filing (and more) so that our partners can build bespoke solutions on top of our infrastructure. Each partner is the perfect expression of “bringing payroll where it should be,” and the result is different manifestations of Check in the wild serving distinctly different business models and employee types equally well, where legacy one-size-fits-none providers just can’t offer that and can’t compete.

How does Check support vertical SaaS, workforce management, financial services, and staffing businesses in their payroll operations?
Since Check’s public launch in January 2021, leading vertical SaaS companies and large scale workforce management and horizontal platforms have built successful payroll businesses on its infrastructure. Check’s over 60 partners collectively serve 3.5m businesses in the U.S. and 20m payees. Check is backed by Stripe, Thrive Capital, Index Ventures, and Bedrock.

What challenges and opportunities arise from supporting payroll services across all 50 states plus D.C., and how does Check ensure compliance and efficiency?
The complexity and patchwork web of rules and laws around compliant payroll in the U.S. is never clearer than when you talk to platforms who’ve attempted U.S. payroll or when you work with international platforms who have started to explore the U.S. payroll market. There is an increasingly complex regulatory framework for platforms to navigate, which has certainly deterred many from building their own solutions. But that complexity, not only as a barrier to entry, but also an ongoing challenge to maintain and stay abreast of the constantly shifting landscape, is precisely Check’s superpower. We obsess over those details so our partners don’t have to. Partners can have their cake and eat it too.

What personal strategies or principles guide your approach to forming and maintaining partnerships at Check?
a. At Check it really boils down to a few simple questions that I’m constantly cycling through: What do our platforms today need for tomorrow? What will the platforms of tomorrow need in the future to be successful? Where is Check uniquely positioned to drive outsized impact for our partners?
b. Once the strategy is defined, we’re really selective about which companies we partner with. In many ways, we see our partnership as an extension of our core offering. Benefits and Payroll go hand in hand. They have to feel like they fit and so it means working with best-in-class partners who are similarly obsessed with their customers and care deeply about making beautiful and powerful solutions for businesses and workers.

Based on your experience, what advice would you give to businesses looking to improve their payroll operations and select the right payroll platform?
If you or your team are moving data, mapping fields, manually tracking information, or using multiple systems to run payroll… there’s a better way. If payroll takes hours, not minutes (or seconds), there’s a better way. The software providers you trust to be the operating system for your business could run your payroll in the same window. Ask them to reach out to Check.

In closing, what final thoughts or key messages would you like to share about the future of payroll technology and the role of partnerships in driving innovation and success in this space?
a. Looking six years back, we have enabled a world in which payroll can fundamentally be not broken, and instead be an asset to any platform. We have created a world of choice, one in which selecting a payroll provider is not one of selecting a lesser evil, but one based on better experiences.
b. The more partners integrate Check’s API, the more end users have access to it. Eventually, small and medium business owners everywhere will not only recognize that their legacy payroll providers no longer fit their needs but will also begin to demand an easier and faster way to do payroll.