Lead Recruiter

About Check

Payroll is broken. Come fix it alongside a team that’s as passionate as you are!

At Check, we’re not just building our own business — we’re building payroll businesses together with every one of our partners. As the inventors of embedded payroll, we’re redefining how people get paid and making it easier for payroll businesses to launch, grow, and thrive.

On our team you'll use creative problem-solving, critical thinking, and grit to simplify the complexity of payroll for thousands of employers of every size, across all industries. We ignore conventional role boundaries in favor of the unique strengths and values each builder brings to our mission: make paying people simple. Check out our origin story!

Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses. See how it works for our partners.

The People Team

At Check, Talent is our highest investment, and Checketeers are the ultimate driver of our long-term growth and success. The People team is dedicated to bringing together skilled and dedicated individuals that can bring our business vision to life, and to fostering an engaged, high-performing team. We aim to create a diverse and equitable workplace where everyone pitches in to achieve incredible things, and every Checketeer is celebrated, supported, and valued for their contributions.

Check is looking for a Lead Recruiter to drive our hiring efforts during a critical growth phase, partnering closely with people leaders across R&D, GTM, and G&A. This role sits at the center of how we build the company. It requires strong judgment, clear communication, deep ownership, and a genuine love for partnering with hiring managers and candidates alike.

You'll be responsible for bringing exceptional people into Check while building real partnership with hiring managers — shaping roles, calibrating bar, and running rigorous-but-human interview processes. To thrive in this role you must care deeply about candidate experience, hiring quality, and the daily business impact of your work, and you should be excited to be a public-facing partner across the leadership team, not a heads-down operations engine.

As you burn through our highest-priority reqs, your scope will broaden into deliberate optimization and infrastructure work: interviewer up-skilling, employer branding, debrief and calibration tooling, and hiring manager enablement at scale.

In this role, you will:

• Own full-cycle recruiting across Engineering, GTM, and G&A with an outcomes-focused mentality. You'll partner with hiring managers to define needs, clarify what great looks like, and engage with top talent to fill those seats.

• Be a true partner to hiring managers from day one. You'll shape roles, drive intake conversations that draw out spicy takes, challenge assumptions, and align teams on Check's standards and needs. Stakeholder partnership is the primary mode of operation here, it’s not optional.

• Run sourcing, outreach, and pipeline-building campaigns that keep candidate flow rich for our highest-priority roles. You'll optimize for quality over quantity to keep efforts efficient.

• Drive recruiting operations within Ashby, leveraging the platform's AI-augmented sourcing, search, and pipeline tools to amplify your reach and impact. You’ll continually explore new ways to help our team make great hiring decisions quickly, while keeping candidates excited about Check.

• Scale our recruiting function as we grow from 85 → 100 → 150 FTEs and beyond, always building with ROI and stakeholder experience in mind.

• Set and maintain a high performance bar for talent while moving fast. You'll keep the big picture in mind, ensuring strong long-term staffing decisions and helping us dodge negotiation traps.

• Work in the open. You'll be a public partner to hiring managers and an active voice in our recruiting channels. We don't need a quiet ops engine. We need someone visible, opinionated, and trusted.

• Partner closely with the Head of People to build creative and engaging hiring loops, competitive compensation structures, effective training programs, and executive reporting capabilities - you’ll continually raise the visibility of the work you do and maximize its impact on every aspect of the business!

Many backgrounds could fit this role, but ideal candidates will have:

• 5+ years of in-house recruiting experience across multiple disciplines (technical and non-technical), preferably in a fast-paced startup or growth-stage environment.

• AI fluency as a core competency — proven ability to leverage AI tools to amplify sourcing, outreach, screening, and decision-making, while applying judgment about where AI helps and where it doesn't. We're hiring people who are strong in their domain and know how to scale that strength through AI.

• Fluency with Ashby and LinkedIn Recruiter (or proven ability to ramp quickly on Ashby — we recently migrated and our system is in active use).

• Proven ability to own full-cycle recruiting independently — sourcing through coordination, closing, and offer management, with a stakeholder-partnership-first orientation.

• Strong sourcing capability, including outbound outreach and pipeline building for hard-to-fill roles.

• Clear, direct communication and exceptional storytelling. You're equally adept at influencing senior stakeholders and selling candidates on a vision.

• Strong judgment and the ability to maintain a high talent bar under time pressure — there's urgency, and then there's false urgency. You know the difference.

• A bias toward visibility — working in the open, speaking up in cross-functional spaces, building hiring-manager confidence through engagement, not invisible reliability.

• Comfort with ambiguity — you're comfortable laying the track when the train is already moving, and always helping our team move faster without sacrificing the integrity of our process.

Travel & Office Policy

The Check team is distributed across the US. Roles can be remote, hybrid, or based in one of our offices in New York City or San Francisco. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons throughout year. All Checketeers gather in the spring for our annual 3-day company retreat.

For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays and there are regular happy hours, game nights, and other in-person events.

Remote work at Check requires the ability to perform all responsibilities without distraction or disruption, while maintaining quality, effective communication, and productivity.

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Check is proud to be an Equal Opportunity employer. We do not discriminate based on race, religion, color, national origin, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender, gender identity, gender expression, transgender status, sexual stereotypes, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, provided they are consistent with applicable federal, state, and local laws. Check is committed to providing reasonable accommodations for candidates with disabilities in our recruiting process.

Check participates in E-Verify and will provide the federal government with Form I-9 information from all new employees to confirm that they are authorized to work in the U.S. Check does not use E-Verify to pre-screen applicants.