Head of People

What is Checkmate?

Checkmate is an AI marketing platform modernizing eCommerce by enabling smarter, more connected buying experiences between brands and consumers.

Powered by AI, Checkmate enhances high-intent buying moments; delivering personalized, timely messaging that meets consumers where they are and drives them to act. By partnering with brands, Checkmate unlocks net-new revenue by reaching high-intent shoppers brands can’t otherwise access.

We’ve expanded our consumer reach beyond our fast-growing app (2M+ shoppers) to a broader network of 100M+ high-intent U.S. consumers. Our platform uses AI to de-anonymize site traffic, uncover missed conversion opportunities, and launch high-performance campaigns that engage shoppers who are ready to buy.Checkmate offers three core products for brands:

1. Enrichment: Reveal and resolve anonymous visitors to fuel smarter lifecycle flows.

2. Targeting: Deliver single-use offers through high-converting surfaces like our app, extension, email, and SMS.

3. Audiences: Capture pre-checkout emails via gated discounts and gain competitive insights.

Backed by GV, Fuel Capital, Blackbird Ventures, Susa Ventures, F7 Ventures, Wischoff Ventures, and cultural icons like Paris Hilton and The Chainsmokers, Checkmate is poised to disrupt how brands connect with consumers.

People at Checkmate

Surprisingly, people have always existed at Checkmate, but now we’re hiring for an official function. This last year, e have 4x’d in revenue, launched a new product that’s garnered a significant amount of interest, and well - that means we want to hire quite a bit more to support that growth + our team.

This function will help scale and build out our hiring strategy, the people function (HR + culture), be a thought leader in employee retention, development and benefits.

Chiefly - the main purpose of this role will be the be able to source excellent talent, build an amazing pipeline, assess and create a thoughtful but efficient interview process, and then retain and develop that individual.

Our company is growing, but growing efficiently. We’d want you to be able to wear many hats within the People function.

Who we’re looking for?

• We’re looking for someone who has a great nose for talent. That is priority number #1. We hire fast at Checkmate from first interview (<2 weeks), but also very thoroughly. As the Head of People, you’ll have a good understanding of what our product does, and the correct pieces of the puzzle to hire and get us to next stage of our business. You should be able to treat recruiting like a funnel and constantly be building great networks where you can source candidates for.

• Someone who knows (or can quickly learn) about benefits, immigration (part of our team is Australian), state compliance (we have >5 states where everyone is based out of and have no immediate plans of being in-person).

• “Put your head over the onion.” Don’t worry — all it means is, be willing to dive in and do the work. The ideal person isn’t afraid to start building up a pipeline of candidates in Day 1, creating onboarding + ramp plans schedules for candidates Day 5, talking to Head of functions on Day 14 to gauge hiring needs… etc.

Roles & Responsibilities

• You’re a top class recruiter and know how to find + nurture great talent, build a world-class interview process, wrangle sheep during hiring, and help candidates (+ current employees) maximize their potential.

• You care about the product. If someone asked you a question on “How does Targeting work” you don’t immediately go towards “Let me get an Eng to tell you”. Instead, you live and breathe our roadmap and are bought into our company journey.

• You bring 6+ years of people experience, running recruiting, HR, compliance, with a deep understanding of payroll, benefits, and can circumvent state compliance (or read some docs) to get us there.

• Build in fostering talent internally, creating pathways for growth, obsessed about pushing managers and ICs to up-level themselves, performance manage, and scale people with tact

Hiring process

• Chat with Shounak (Head of Ops)

• Assessment

• Chat with Harry + Rory (co-founders)

• Meet the team

• Decision

Benefits 💸

• Competitive salary

• Healthcare

• Gym membership

• 4 weeks PTO and health days

• Company retreats 🏝

• Additional benefits

• US remote - Los Angeles or New York City preferred