Checkstep provides AI-powered content moderation and Trust & Safety solutions to online platforms. We work with:
* Marketplaces
* User-generated content platforms
* AI-native platforms
As regulation such as the EU Digital Services Act increases accountability for platforms, Checkstep enables organisations to combine automation, policy enforcement, and human oversight at scale.
The Role
We are hiring two Enterprise New Business Executives with a clear mandate: deliver £/$600–800k in annual net-new ARR through full-cycle enterprise sales.
This is a 90% new business role with typical deal sizes ranging between £/$60–80k ACV.
You will own the full sales cycle end-to-end — from outbound prospecting and qualification through demo, POC leadership, negotiation, and close. Success in this role typically requires closing 8–12 new enterprise logos annually.
You will collaborate with Customer Success and Partnerships post-sale, but your primary accountability is acquiring new logos and consistently delivering against quota.
This role requires a disciplined operator who thrives in evolving environments and is capable of building structure while executing at pace.
This is not a farming role.
Key Responsibilities
1. New Business Acquisition (Primary Focus)
* Generate and close £/$600–800k in annual net-new ARR
* Close 8–12 new enterprise customers per year
* Build and maintain pipeline coverage aligned with quota expectations
* Drive outbound-led opportunity generation
* Lead complex, multi-stakeholder consultative sales cycles (technical + commercial)
* Own and lead POCs from scoping through validation and commercial conversion
* Negotiate commercial agreements and close contracts
2. Pipeline, Reporting & Commercial Discipline
* Maintain rigorous CRM hygiene (HubSpot)
* Deliver reliable monthly, quarterly, and rolling forecasts
* Operate with structured qualification methodologies
* Create clarity where needed — improve reporting frameworks, tracking methods, and sales processes
* Strengthen lead generation effectiveness through structured feedback loops
* Contribute to building scalable commercial infrastructure
3. Strategic & Cross-Functional Contribution
* Partner closely with Marketing, Product, Partnerships, and Leadership
* Provide structured market intelligence and competitive insights
* Contribute to vertical prioritisation and GTM refinement
* Build strong internal relationships to ensure seamless execution
What We Are Looking For Mandatory
* Bachelor’s degree in Business, Economics, Management, or related field
* 6–8+ years in B2B SaaS new business sales
* Experience selling AI, Trust & Safety, compliance, or regulatory technology
* Proven history of carrying and exceeding £/$600k+ quotas
* Experience closing enterprise deals in the £/$50–100k ACV range
* Demonstrated ability to manage multiple complex opportunities concurrently
* Experience leading structured POCs or technical evaluations
* Comfortable operating in high-growth, evolving environments
Preferred
* Additional academic background in social sciences, law, public policy, or related disciplines
* Experience selling into digital platforms, policy, compliance, or risk teams
Profile
* Highly self-driven and accountable; does not require close supervision
* Comfortable building structure in environments that are still scaling
* Strong analytical and reporting mindset
* Improves processes rather than waiting for them
* Demonstrates intellectual curiosity and a continuous improvement attitude
* Motivated by impact, ownership, and professional standards — not solely compensation
* Determined to achieve demanding targets
Success in This Role Will Be Measured By
* Net-new ARR closed (£/$600–800k annually)
* Number of new logos acquired
* Pipeline coverage ratio and conversion rates
* Forecast accuracy
* Contribution to commercial process improvement
What We Offer
* Competitive base salary with performance-based upside aligned to quota
* Equity participation
* Remote flexibility
* Health coverage
* 401(k) with employer match (US)
* Annual learning & development budget
* Generous PTO Join Us
Checkstep operates at the intersection of AI, regulation, and platform accountability. We are building infrastructure that enables digital platforms to operate responsibly at scale.
We are looking for disciplined enterprise hunters who can create pipeline, lead complex sales processes, bring structure to ambiguity, and consistently deliver significant net-new revenue.
If you have closed at this level before and want to operate with autonomy and accountability, we would like to speak with you.
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