LESSO has appointed Bee Digital, a specialist education marketing agency, to act as its external marketing arm during this early stage. Bee supports market development, lead generation, campaign execution and pilot recruitment. As CCO, you will own the strategy, direct the agency relationship, set commercial priorities and ensure customer knowledge, pipeline data and learning remain inside LESSO.

The commercial proposition starts with materially reducing the work surrounding teaching and expands into giving schools a controlled environment through which AI can be adopted, measured and governed. The CCO should prove value, not merely market it.

What you will own

• Owning the full commercial and customer lifecycle from lead generation through renewal and expansion.
• Managing Bee Digital as the external demand-generation partner, including lead quality, campaign priorities, funnel performance and pilot recruitment.
• Owning the school and MAT pipeline: qualification, stakeholder mapping, budget ownership, procurement, sales progression, forecasting and close.
• Design the commercial structure of school pilots, define the evidence required for conversion, and own the path from pilot approval to paid contract.
• Building the enterprise sales motion end to end, including how LESSO progresses from an individual school win into trust-wide adoption.
• Owning onboarding, implementation, adoption, customer health, account management, renewal and expansion until dedicated teams are built beneath the function.
• Designing the future Sales / Commercial organisation and the future Customer Success / Adoption / Account Management organisation, including systems, roles, operating rhythms and KPIs.
• Shaping pricing, packaging and contract structures around what schools and MATs can actually buy, not simply what LESSO can build.
• Building the revenue model, commercial forecast, CRM discipline and reporting required for fundraising, board scrutiny and future hiring.
• Creating a disciplined customer-feedback loop so buying objections, onboarding friction, adoption evidence, usage behaviour and renewal risk become structured input for the product team.
• Working closely with the Founding CPTO and potential Founding Chief AI & Data Officer so commercial promises remain grounded in what the product and AI capability can deliver.
• Representing LESSO in strategic customer, partner and investor conversations alongside Luke where appropriate.

The package

This is an equity-bearing co-founder position, not an advisory appointment or an early-employee option grant.

• The founder equity and post-raise compensation package will be discussed directly with credible candidates and will reflect experience, fit, pre-raise contribution, commercial ownership and commitment to join full-time once funded.
• A competitive founder salary and performance-related package will begin once the funding round completes, and the role moves full-time.
• A genuine seat at the table shaping LESSO's category, customer model, pricing and commercial strategy, not simply executing somebody else's playbook.
• You inherit a live product, structured pilots, existing market learning, a confirmed product/technology founder and an external education marketing partner already in motion.
• Remote working, with travel to schools, MATs, events, and strategic meetings as required.

Before the raise

This is an equity-only founding role before the raise, but we are not asking someone to leave an existing position immediately and work full-time without salary until funding lands. Luke is currently building LESSO alongside other commitments and understands the realities of this stage.

The initial pre-raise work will focus on auditing the current pipeline and GTM assumptions, directing the work with Bee Digital, shaping the first pilot cohort, defining qualification and conversion criteria, building the post-pilot commercial journey and establishing the first version of the customer-success and account-management operating model.

The exact commitment will be agreed with the right person. We expect meaningful founder-level ownership before the raise, with the role becoming full-time once funding completes, or earlier where circumstances allow.

Essential experience

• Senior commercial leadership experience with direct responsibility for a pipeline of schools, MATs or comparable education organisations.
• A demonstrable record of successfully selling technology, software or SaaS into the education sector, ideally directly into UK schools and MATs.
• First-hand understanding of SLT buying behaviour, education procurement, budget ownership, stakeholder mapping and multi-stage sales cycles.
• Experience taking opportunities from early qualification through commercial negotiation and signed contract, rather than operating only at lead-generation or partnership level.
• The judgement to distinguish interest from real buying intent and to understand what evidence, urgency and internal champion are required to move a school or MAT forward.
• Strong commercial forecasting and pipeline discipline, with the ability to build a repeatable system rather than rely on individual relationships.
• Comfort owning the customer relationship beyond signature, including implementation, adoption, account health, renewal and expansion while the team is still small.
• The ability to operate autonomously: set commitments, follow through without supervision, communicate early when something changes and take an outcome from problem to resolution.

Highly desirable

• Experience building or scaling both a sales/commercial function and a customer-success, adoption or account-management function.
• Previous founder experience, an exit, or experience operating as a fractional CCO / CRO / senior commercial leader in early-stage businesses.
• Experience expanding from individual school customers into multi-academy trust or group-level contracts.
• Experience selling AI, workflow software, SaaS or other products where adoption and behaviour change matter as much as the initial sale.
• Comfort representing a company in investor, strategic partner and board-level conversations.

How you will operate

This is a founding role. You will be expected to challenge assumptions, make decisions, build beyond a narrow job description and take responsibility for outcomes. LESSO is moving quickly through pilots, team formation and fundraising, so dependable follow-through and transparent communication matter as much as experience.

We are looking for someone who wants ownership, not simply a senior sales title.

Apply

If you have built and managed a school or education technology pipeline, know what it takes to turn interest into signed contracts and want to build the commercial and customer engine behind a category-defining company, get in touch.