Checkmate
Overview
Checkmate is a global Workforce Compliance and Risk OS, empowering organisations to hire and manage safer, more compliant, and more productive workforces. We’re transforming how businesses identify, mitigate, and monitor workforce risk, delivering trust, compliance, and operational certainty at scale. We’re expanding our U.S. team and looking for an ambitious, people-driven Account Executive to lead outbound sales, manage inbound opportunities, strengthen client relationships, and activate partner-sourced growth. Role Overview As our Account Executive, you’ll be a key growth driver for Checkmate’s U.S. mid-market, owning the full sales cycle from pipeline creation to close, onboarding support, and ongoing relationship management. You’ll focus on outbound prospecting, managing inbound leads, developing event-driven demand, nurturing client relationships, and working closely with integration and channel partners to generate sustainable, long-term growth. You’re a hunter and a farmer: confident in outbound sales, skilled at discovery and demos, and passionate about maintaining relationships that lead to upsell, cross-sell, referrals, and advocacy. Key Responsibilities 1. Pipeline Generation (Outbound & Inbound)
Identify and target ideal customer profiles across priority verticals (healthcare, aged care, education, construction). Lead structured outbound campaigns through LinkedIn, HubSpot, and automation tools. Respond to and qualify inbound leads rapidly, turning interest into discovery meetings. Maintain an active pipeline with accurate forecasting and CRM discipline. 2. Sales Discovery, Demos & Closing
Conduct discovery calls to uncover client goals, challenges, and compliance needs. Deliver tailored demos and proposals that demonstrate Checkmate’s value and ROI. Manage full sales cycles from qualification through to contract negotiation and close. Collaborate with Sales Engineering, Product, and Customer Success for smooth handover and onboarding. 3. Account Management & Relationship Growth
Build and nurture strong client relationships post-sale to ensure satisfaction and renewal. Identify opportunities for upselling, cross-selling, and expanding Checkmate’s footprint within existing accounts. Leverage happy customers for referrals, case studies, and advocacy. Organise and participate in client appreciation and networking events to strengthen engagement. 4. Events & Field Marketing
Represent Checkmate at key industry events, conferences, and partner roadshows. Collaborate with marketing to plan and deliver regional events, workshops, and client sessions. Drive post-event follow-up and lead conversion to maximise ROI. 5. Partnerships & Alliances
Co-market and co-sell with ATS/HRIS integration partners. Build relationships with consulting, compliance, and industry partners for joint opportunities. Maintain a quarterly partnership cadence and shared pipeline metrics. 6. Collaboration & Continuous Improvement
Share client feedback and market insights to inform product and marketing strategies. Contribute ideas to enhance the sales playbook, messaging, and customer experience. Participate in internal team meetings and training to refine sales skills and industry knowledge. What Success Looks Like
Consistent attainment of pipeline, revenue, and retention targets. A healthy balance of outbound, inbound, and referral-sourced opportunities. Strong conversion rates across discovery, demo, and close stages. Active account growth through upsells, cross-sells, and renewals. High client satisfaction and engagement scores. Strong visibility at key events, representing Checkmate with professionalism and energy. Skills & Experience
3–5 years’ SaaS sales experience, ideally within HR tech, compliance, or B2B SaaS. Proven success managing both outbound and inbound sales cycles. Experience nurturing client relationships and driving account growth. Skilled in discovery, solution selling, and demo delivery. Comfortable with CRM systems (HubSpot preferred) and automation platforms. Excellent communication, presentation, and interpersonal skills. Confident event presence and strong networking capability. Willingness to travel domestically and internationally (approx. 20%). Why Join Checkmate
Help shape the future of workforce compliance and risk management. Join a high-growth, mission-driven global team. Competitive base salary, commission, and stock options. Global travel opportunities, autonomy, and visibility with senior leadership. Opportunity to grow your career within a rapidly scaling SaaS company redefining how organisations manage workforce risk.
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Checkmate is a global Workforce Compliance and Risk OS, empowering organisations to hire and manage safer, more compliant, and more productive workforces. We’re transforming how businesses identify, mitigate, and monitor workforce risk, delivering trust, compliance, and operational certainty at scale. We’re expanding our U.S. team and looking for an ambitious, people-driven Account Executive to lead outbound sales, manage inbound opportunities, strengthen client relationships, and activate partner-sourced growth. Role Overview As our Account Executive, you’ll be a key growth driver for Checkmate’s U.S. mid-market, owning the full sales cycle from pipeline creation to close, onboarding support, and ongoing relationship management. You’ll focus on outbound prospecting, managing inbound leads, developing event-driven demand, nurturing client relationships, and working closely with integration and channel partners to generate sustainable, long-term growth. You’re a hunter and a farmer: confident in outbound sales, skilled at discovery and demos, and passionate about maintaining relationships that lead to upsell, cross-sell, referrals, and advocacy. Key Responsibilities 1. Pipeline Generation (Outbound & Inbound)
Identify and target ideal customer profiles across priority verticals (healthcare, aged care, education, construction). Lead structured outbound campaigns through LinkedIn, HubSpot, and automation tools. Respond to and qualify inbound leads rapidly, turning interest into discovery meetings. Maintain an active pipeline with accurate forecasting and CRM discipline. 2. Sales Discovery, Demos & Closing
Conduct discovery calls to uncover client goals, challenges, and compliance needs. Deliver tailored demos and proposals that demonstrate Checkmate’s value and ROI. Manage full sales cycles from qualification through to contract negotiation and close. Collaborate with Sales Engineering, Product, and Customer Success for smooth handover and onboarding. 3. Account Management & Relationship Growth
Build and nurture strong client relationships post-sale to ensure satisfaction and renewal. Identify opportunities for upselling, cross-selling, and expanding Checkmate’s footprint within existing accounts. Leverage happy customers for referrals, case studies, and advocacy. Organise and participate in client appreciation and networking events to strengthen engagement. 4. Events & Field Marketing
Represent Checkmate at key industry events, conferences, and partner roadshows. Collaborate with marketing to plan and deliver regional events, workshops, and client sessions. Drive post-event follow-up and lead conversion to maximise ROI. 5. Partnerships & Alliances
Co-market and co-sell with ATS/HRIS integration partners. Build relationships with consulting, compliance, and industry partners for joint opportunities. Maintain a quarterly partnership cadence and shared pipeline metrics. 6. Collaboration & Continuous Improvement
Share client feedback and market insights to inform product and marketing strategies. Contribute ideas to enhance the sales playbook, messaging, and customer experience. Participate in internal team meetings and training to refine sales skills and industry knowledge. What Success Looks Like
Consistent attainment of pipeline, revenue, and retention targets. A healthy balance of outbound, inbound, and referral-sourced opportunities. Strong conversion rates across discovery, demo, and close stages. Active account growth through upsells, cross-sells, and renewals. High client satisfaction and engagement scores. Strong visibility at key events, representing Checkmate with professionalism and energy. Skills & Experience
3–5 years’ SaaS sales experience, ideally within HR tech, compliance, or B2B SaaS. Proven success managing both outbound and inbound sales cycles. Experience nurturing client relationships and driving account growth. Skilled in discovery, solution selling, and demo delivery. Comfortable with CRM systems (HubSpot preferred) and automation platforms. Excellent communication, presentation, and interpersonal skills. Confident event presence and strong networking capability. Willingness to travel domestically and internationally (approx. 20%). Why Join Checkmate
Help shape the future of workforce compliance and risk management. Join a high-growth, mission-driven global team. Competitive base salary, commission, and stock options. Global travel opportunities, autonomy, and visibility with senior leadership. Opportunity to grow your career within a rapidly scaling SaaS company redefining how organisations manage workforce risk.
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