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For Companies At a Glance
- Tasks: Drive sales and expand market presence for AI-driven content moderation solutions.
- Company: Join Checkstep, a leader in digital safety and AI technology.
- Benefits: Equity options, remote flexibility, full health coverage, and generous PTO.
- Why this job: Make a real impact on online safety while shaping the future of a fast-growing startup.
- Qualifications: 4+ years in B2B SaaS sales with a passion for AI and online safety.
- Other info: Opportunity for career growth into leadership as we scale.
The predicted salary is between 36000 - 60000 £ per year.
About Checkstep
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.
The Role
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.
Join Us
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.
Enterprise Account Executive in Slough employer: Checkstep
Contact Detail:
Checkstep Recruiting Team
StudySmarter Expert Advice 🤫
We think this is how you could land Enterprise Account Executive in Slough
✨Tip Number 1
Network like a pro! Get out there and connect with people in the industry. Attend events, webinars, or even local meetups. The more you engage, the better your chances of landing that Enterprise Account Executive role.
✨Tip Number 2
Do your homework on Checkstep! Understand their mission and how they tackle content moderation challenges. When you know the ins and outs of what they do, you can tailor your pitch and show them why you're the perfect fit.
✨Tip Number 3
Practice your sales pitch! Role-play with a friend or mentor to refine your consultative selling approach. Being able to clearly articulate how you can help clients navigate their trust and safety needs will set you apart.
✨Tip Number 4
Apply through our website! It’s the best way to ensure your application gets seen by the right people. Plus, it shows you’re genuinely interested in joining the Checkstep team and making a difference in online safety.
We think you need these skills to ace Enterprise Account Executive in Slough
Some tips for your application 🫡
Tailor Your Application: Make sure to customise your CV and cover letter for the Enterprise Account Executive role. Highlight your experience in B2B SaaS sales and any relevant knowledge of AI and online safety. We want to see how you can bring value to our mission!
Showcase Your Achievements: Don’t just list your responsibilities; share your successes! Include specific examples of how you've met or exceeded sales targets in previous roles. This helps us understand your impact and potential.
Be Authentic: Let your personality shine through in your application. We’re looking for someone who’s not only skilled but also a great fit for our team culture. Share your passion for online safety and how it aligns with our values.
Apply Through Our Website: We encourage you to apply directly through our website. It’s the best way for us to receive your application and ensures you don’t miss out on any important updates from our team. We can’t wait to hear from you!
How to prepare for a job interview at Checkstep
✨Know Your Stuff
Before the interview, dive deep into Checkstep's mission and products. Understand how their AI-driven content moderation works and be ready to discuss how your experience aligns with their goals in building safer digital spaces.
✨Showcase Your Sales Skills
Prepare to share specific examples of how you've successfully generated new business opportunities in previous roles. Highlight your consultative sales approach and how you've tailored solutions to meet client needs, especially in the B2B SaaS space.
✨Engage with the Team
Since this role involves collaboration with various teams, be prepared to discuss how you’ve worked cross-functionally in the past. Show enthusiasm for working closely with leadership, marketing, and product teams to shape strategies and messaging.
✨Ask Insightful Questions
Prepare thoughtful questions that demonstrate your interest in Checkstep’s challenges and future direction. Inquire about their approach to compliance with regulations like the EU Digital Services Act and how they envision the evolution of online safety.
