Fractional Chief Commercial Officer - 6+ Months (2-4 days pw)

About Us

We are a mission-driven accessibility start-up dedicated to transforming how neurodivergent individuals navigate their educational and professional journeys. 

Since launching our first product, Present Pal, back in 2018, Estendio has empowered students across over 150 universities in the UK and US to excel in their presentations and communication skills. Building on this success, we recently launched our second product, Tailo, an AI-powered reading platform designed to create a tailored reading experience for every mind.

Our vision is to make inclusivity the standard, not the exception. If you’re ready to join a brillian team committed to levvelling the playing field through tech for good, we’d love to hear from you.

About the Role

We're looking for a Fractional Chief Commercial Officer for a focused 6-7 month engagement (mid-September 2026 to March/April 2027).

The mission is specific: define and deliver Estendio's first repeatable, scalable B2B institutional pipeline for Bifrost. This is a pointed commercial project - not a seat-warmer.

This is a senior, hands-on commercial role. You'll inherit two products in active validation: Tailo, an AI-powered reading platform for students (B2C), and Bifrost, an AI-powered document accessibility solution built for higher education (B2B).

The primary focus is B2B - defining a route to revenue, landing and closing institutional deals for Bifrost. Depending on the September go/no-go outcome, we may choose to run a dual-track approach, with Bifrost and Tailo (B2C) active in parallel. You’ll need to be comfortable leading across both tracks; if we go dual, a dedicated B2C advisor will support alongside you.

By the time you start, a September go/no-go decision on Bifrost will have shaped the strategic direction - but you'll need to be comfortable operating across both tracks regardless of the outcome. You'll manage a small, capable team (a Senior Marketing Lead and, a newly hired Marketing Manager, a Senior Education Lead and Head of Commercial), and report directly to the CEO.

If you thrive in early-stage environments where the strategy is still being written, this role will suit you.

What you'll be doing - Key Responsibilities

B2B: Institutional Sales and Deal Strategy

• Work alongside the Head of Commercial to navigate complex institutional sales cycles - CIO and LMS director conversations, procurement processes, compliance requirements, and budget approvals

• Help structure deals that can get through - understanding how universities buy, what procurement needs to see, and how to position pricing for different institution types

• Work closely with the Head of Commercial to build and optimise the commercial pipeline - lead qualification, deal progression, and conversion tracking

• Build the GTM infrastructure around sales: CIO-targeted content, case studies, ABM campaigns, sales enablement materials, and outreach sequences

• Define and track commercial KPIs - pipeline progression, conversion rates, deal size, and time-to-close

• If Bifrost validates: accelerate the sales motion and support hiring of an Account Executive. If it doesn't: help the team pivot and reallocate resource

• Work closely with the Director of Product and CTO to develop and sharpen the overarching value proposition - acting as the commercial voice in product and strategy conversations

Own our Commercial and GTM Strategy

• Lead the go-to-market function across both product lines, adapting the strategy as validation signals come in

• Define what success looks like for each track - and what "not working" looks like

• Report weekly learnings and recommendations to the CEO

Lead and Develop the Team

• Manage the Senior Marketing Lead (full-time), the new Marketing Manager and set direction for day-to-day execution

• Brief and re-integrate the B2B Marketing Manager when she returns in January

• Orchestrate freelancers and contractors, ensuring activity aligns with learning objectives

About You

Experience

• Higher Education sector experience is strongly preferred - existing networks and domain knowledge will meaningfully accelerate Bifrost validation.

• Significant B2B SaaS GTM experience - you've marketed to institutional or enterprise buyers, ideally in education or a regulated sector

• Experience in early-stage or pre-revenue environments where you had to validate before scaling

• Comfortable managing small teams and working with senior leadership

Skillset

• Comfortable with ambiguity: You'll join mid-pivot. The strategic direction will still be forming. You see that as an interesting challenge, not a red flag.

• Experiment-driven: You'd rather test, learn, and pivot than stay stuck in planning. You set clear learning goals and budget caps before spending.

• Candid and decisive: You have the confidence to say "this isn't working" and recommend a change of direction. You value progress over being right.

• Curiosity over assumptions: You ask "why" constantly, listen to learn, and let data and user insight drive your recommendations.

• Resilient through direction changes: Early-stage strategy pivots - sometimes fast. You can hold the line when it does, keep the team focused, and adapt without losing momentum or confidence.

What We Offer

• 9-day fortnight - every second Friday off. A major benefit that we all love

• Remote working - work from home, or a co-working space. What matters is that you do your best work

• Flexibility - core hours flexi system so you can organise your day around what works for you

• EMI options - the hard work comes from everyone, so we want the whole team to share in the success

• Home working budget - £150 towards your home office set-up

• Tools and tech - MacBook as standard, plus whatever else you need to stay connected and do your best work

• Assistive technology - we mean what we say about accessibility, and we'll set you up with the tools you need

• Socials - quarterly in-person get-togethers with a team committed to making real impact through tech for good (and having a laugh along the way)

• Make a real impact - building inclusive tech for every mind

• Location: Remote (Based in the UK)

📣 Other Notes

Please Note: You must be based in the UK and have the right to work in the UK

• Remote, with a distributed team across the UK. You'll need to be available to travel across the UK (sometimes up to Glasgow) a minimum of four times per year for company events.

Our Recruitment Process

• Diversity, Equity and Inclusion are at the heart of who we are and what we do. Estendio is a Disability Confident Employer, and we aim to make your recruitment experience as accessible as possible. If you have any additional support needs, please let us know and we'll work with you throughout the hiring process.

• We believe interviews are a two-way process, and finding a great fit for you and our team - ask us anything you like.

Ready to help us level the playing field? We’d love to hear from you.