Enterprise Account Executive in England

Checkstep is at the forefront of building safer digital spaces by providing AI-driven content moderation and trust & safety solutions for online platforms. Our platform empowers Trust & Safety teams with flexible workflows, moderation tooling, and cutting-edge machine learning to automate harmful content detection and policy enforcement at scale. We work with forward-thinking platforms across social media, marketplaces, gaming, and beyond to help them meet regulatory requirements and user safety expectations. Our technology is already helping reduce the spread of harmful content, protect vulnerable communities, and support compliance with major international laws, all while allowing our customers to maintain focus on growth and innovation.

As AI reshapes the future of digital content, Checkstep ensures platforms are equipped to handle the challenges of today and tomorrow, from compliance with the EU Digital Services Act to moderating nuanced content such as hate speech, misinformation, and CSAM. If you're passionate about helping tech platforms build trust with their users, we’d love to talk.

We are seeking a driven and experienced Enterprise Account Executive to join our growing sales and business development team. At Checkstep, our Account Executives are critical to our mission, enabling platforms to deploy trustworthy, scalable content safety solutions. In this role, you will work directly with the commercial and leadership teams to expand our market presence, grow existing relationships, and close new business. You'll play a key role in bringing our AI-powered platform to some of the most pressing content safety challenges faced by digital platforms today. This is a strategic, full-cycle sales role focused on mid-to-late stage technology companies and global enterprises. You'll also have a clear growth path: as one of the early hires in our sales team, you'll help shape our GTM strategy and have the opportunity to build and lead a team as we scale.

Responsibilities

• Identify and generate new business opportunities through outbound efforts, inbound lead qualification, and strategic partnerships
• Build and manage a robust sales pipeline across multiple verticals including social media, marketplaces, gaming, and online communities
• Guide prospects through a consultative, solutions-based sales process from initial contact to close and onboarding
• Develop a deep understanding of client needs and how Checkstep’s products can address key pain points and regulatory obligations
• Collaborate closely with Checkstep’s leadership, marketing, and product teams to tailor GTM strategy and messaging
• Deliver product demos and proposals, manage RFPs, and negotiate contracts with mid-market and enterprise clients
• Maintain up-to-date records and forecasting accuracy within our CRM (HubSpot)
• Gather market intelligence and customer feedback to help inform product development and positioning
• Consistently achieve and exceed quarterly and annual revenue targets

Requirements

• Bachelor’s degree or equivalent practical experience
• 4+ years of experience in B2B SaaS sales, ideally selling AI, Trust & Safety, or compliance-related technology
• Proven track record of meeting or exceeding quota in high-growth environments
• Strong interest in AI, online safety, and digital platform regulation (e.g., DSA, UK Online Safety Act, etc.)
• Excellent communicator with the ability to engage both technical and non-technical stakeholders
• Comfortable working in a fast-paced, startup environment with a global customer base
• Highly organized, self-driven, and proactive, a natural relationship builder and problem-solver
• Prior experience selling into trust & safety, compliance, platform policy, or moderation teams is a plus

What We Offer

• Equity options
• Remote work flexibility in the US and hybrid work in London
• Full health coverage (medical, dental, vision)
• Annual learning and development stipend
• Home-office budget to support your remote setup
• Generous PTO and local public holiday coverage
• Opportunity to shape the sales function of a fast-growing AI startup
• Direct impact on how the internet becomes safer and more trustworthy
• Career path into leadership and team-building as we scale the commercial function

Time Zone & Travel

We are a globally distributed team with hubs in both the US and Europe. This role requires a minimum of 4 hours of daily overlap with GMT or CET working hours. Occasional travel may be required for customer meetings, team summits, or industry events.

At Checkstep, we're solving some of the toughest problems in content moderation and online safety — and we’re just getting started. We operate with integrity, transparency, innovation, neutrality, and ambition at our core. If you’re excited about working at the intersection of AI, policy, and platform trust, we’d love to hear from you.