Sales Director


  • Full Time

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Chatterbox is looking for it’s first Sales Director. Collaborating cross-functionally with both marketing and product teams, you will help to shape a unique and delightful customer experience in the SaaS EdTech space for a range of corporate clients. The Chatterbox language learning platform is anything but ordinary, having garnered significant press and won the support of mostly blue-chip corporate clients since its inception.

As Sales Director, you will work closely with our CEO to develop our corporate sales strategy and take full ownership of delivering our B2B growth. Initially applying your expertly honed communication, negotiation, and marketing skills to become an expert seller of Chatterbox yourself, you will be responsible for building, training, and managing an A- team of sellers across new and renewal sales to help us 10x our revenue. This is a role with significant influence within the organisation, offering the right candidate the potential to grow significantly and have impact across the organisation as we scale globally.



SALES – Leading by example, becoming an expert at selling Chatterbox to B2B clients. Partnering with customers to understand their business needs and objectives. Building and maintaining strong, long-lasting customer relationships.

LEADERSHIP – Being responsible for managing all sales operations, hiring a starting A-team of sellers for Chatterbox, tripling our headcount in 12 months. Training and developing our Account Executives, Sales Development Representatives and Customer Success Managers to be the best they can be, driving a culture of sales excellence within sales and the wider organisation.

REVENUE MANAGEMENT – Owning the design, execution and success of marketing and sales campaigns to hit/exceed annual sales targets, optimize buyer engagement and maximise sales conversions. Managing operational teams to ensure customer execution results in customer success to reduce churn, maximize customer retention, increase cross-sell and upsell. Collaborating with customer success teams to ensure they are executing effectively to maximize retention, up-sell and cross-sell.

STRATEGY DEVELOPMENT – Working alongside the CEO to design and implement strategic plans for B2B growth. Taking full ownership of strategic implementation within the sales team, developing key sales strategies, tactics and action plans. Fine-tuning Chatterbox’s value proposition, sales processes, playbooks, training plans and methodology. Setting targets & creating competitive compensation structures for the sales team. Reporting on revenue performance and helping to shape wider business targets and the design of the Chatterbox product.


  • A strong and inspiring communicator
  • Extensive experience in B2B sales
  • A proven track record of managing teams closing deals over £200,000
  • Track record of success operating in the complex and challenging early stage of a business’ lifecycle
  • Data driven and financially literate, comfortable with projections and financial analysis
  • Extensive knowledge of the B2B customer journeys
  • Previous experience within business and people leadership, setting down a vision and strategy and mobilising teams across all functions (experience operating at Board-level or with founders is a plus)

Other than a competitive salary, we’re proud to support our team members with:


We’re a VC-backed startup looking to produce systemic change by unlocking talent in marginalised communities. We’re supported by some of the best early stage partners in the world, including startup studios All Turtles, Founders Factory, and GMG Ventures. They will become a part of your team too.


The Chatterbox founders first started working together between the sandy beaches of Lisbon and the cityscapes of London. Today, we’re a global and remote-first company with an office in both tech hubs. You can choose to work from either of our offices in Lisbon or London, or 100% remotely from anywhere in the world – whatever suits you best, as long as you’re functional in GMT.


We’ve always worked remotely so know a thing or two about how to build thriving working relationships and a close-knit company culture remotely, currently across 5 countries. For those who like in-person events, we have quarterly team retreats, co-working and socials in London/Lisbon, and a ‘Chatterbox House’ in each city to host members of our team overnight if they would like to visit.


“The best minds of my generation are thinking about how to make people click ads. That sucks.” Joining us, you will be working on a social problem that genuinely matters; the global opportunity gap that causes talented people from marginalised backgrounds to become long-term unemployed. As an early stage startup, your work with us will have an even bigger impact on the future of our company and movement.


Because you can’t be superwoman or superman without the right cape and boots. We offer magical quarterly team retreats, an annual personal learning budget, and the opportunity to invest in your own success with EMI-qualifying share options in Chatterbox. Oh, and unlimited free language learning (naturally 😉).


Founded by an award winning social entrepreneur and a Y-combinator alum, Chatterbox is on a mission to shake things up in the labour market by connecting the world’s most talented, yet marginalised, people with opportunities in the online economy. Our AI-powered, multi-award winning language learning platform matches marginalised people in need of work with opportunities in the digital economy.

Our startup has sparked interest from the likes of the Guardian and the BBC, as well as backing from leading investors in Europe and Silicon Valley, as a social innovation capable of radically and permanently tipping the scales towards a more just global economy. This is a rare opportunity to work in a high-growth, VC-backed startup with global social impact embedded at it’s core – supporting an incredible yet marginalised community who inspire and motivate our team every day. Join us and spend your time and skills building technology that really matters, from the ground up, with a global team of industry leaders.


We believe in fostering a diverse and inclusive workplace. Therefore, we want to make sure that our recruitment process is accessible to everyone. So if you need any reasonable adjustments – at any point in the process – we’ll do our best to help. Just let us know what you need on your application form or reply with your request to the email we send you after you have applied.

We’re also usually hiring several roles at once – if you recommend someone who lands any of our paid roles we can offer you a reward of £250 to thank you for adding another valuable member to our family. You can also sign up to hear about future roles on this career site.

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