Checkmate is workforce compliance software used by major employers across New Zealand, Australia, and the US. We sit at the intersection of HR technology, compliance, and data intelligence, and we're expanding rapidly across APAC.

We're a tight team that moves fast, cares about the product, and treats every customer relationship as a long-term partnership. Joining us at this stage means real impact, real autonomy, and a seat at the table as we scale.

The Role

This isn't a classic quota-and-close sales role. You'll operate as a trusted advisor across enterprise accounts, strategic partners, and the broader ecosystem we operate in. You'll work closely with our product team, bring customer intelligence inward, and represent Checkmate outward with credibility and depth.

We want someone who's been around long enough to know that the best deal is the one both sides are glad they did, a year later. Minimise risk. Maximise potential. Add genuine value to every conversation you enter.

What You'll Do

• Lead the full enterprise sales cycle - from pipeline development through to close and expansion, with a focus on long-term account health
• Build and deepen relationships with enterprise stakeholders across HR, Legal, Procurement, and the C-suite
• Activate and grow strategic partnerships - working with our Partners team to identify, develop, and leverage referral and integration relationships
• Be a bridge between customers and our product team - translating real-world friction into product intelligence that shapes our roadmap
• Show up as a genuine participant in the HR tech ecosystem - industry events, associations, and networks where our customers live
• Protect and grow net revenue retention across your accounts; upsell and cross-sell where it genuinely makes sense
• Maintain rigorous pipeline hygiene in HubSpot and hold yourself to high standards on forecast accuracy

Who You Are

You've been in enterprise sales long enough to know that relationships are the product. You don't just work your accounts - you understand their businesses, their risks, and what keeps their leaders up at night. You bring solutions before you're asked.

• 5+ years enterprise B2B sales experience, ideally in HRtech, SaaS, or professional services
• A proven track record of hitting and exceeding targets - with retention metrics you're equally proud of
• Strong existing relationships across HR, talent acquisition, or compliance functions at enterprise level
• Experience working alongside partners and channels, not just direct
• A collaborative mindset - you loop in product, you support CS, you share market intelligence freely
• Commercial rigour: you understand margin, risk, contract terms, and the difference between a good deal and a great one
• You're active in your industry. You know the names. You're known.

What Good Looks Like

After 12 months, you'll have built a high-quality enterprise pipeline with strong conversion, established yourself as the go-to person for your accounts, delivered meaningful partner-sourced pipeline, and contributed product insights that made it onto the roadmap. Renewal is never in question.

The Package

• Competitive base + uncapped commission
• Equity participation for the right person
• Flexible working — outcomes over optics
• Annual team retreat (past stops: Bali, Queenstown, San Fran)
• Genuine career trajectory in a scaling business

If this role interests you, please reach out and let's grab a coffee.