SideLight AI
Commercial Director
How your CV stacks up
Upload your CV to see how well it fits this job role
?%
Commercial Director
Full-time | Remote | UK
Help reshape how complex injury claims are investigated and resolved
SideLight is building the operating system for clinical negligence and personal injury litigation. Our platform helps legal teams assess the merits and risks of a claim, organise complex medical evidence, build chronologies and collaborate with experts and counsel — from initial instruction through to resolution.
We combine advanced AI with optional clinical human oversight, giving lawyers speed without sacrificing confidence in the evidence.
We are now looking for a Commercial Director to help take SideLight through its next stage of growth.
The opportunity
This is not a traditional legal sales role.
We are looking for someone who understands how complex claims actually progress: how cases are screened, where fee-earner time is lost, how medical evidence shapes strategy and why promising technology often fails to translate into everyday legal practice.
You may be a clinical negligence or personal injury lawyer considering a move away from fee-earning. You might already be working in legal technology, insurance, litigation services or business development.
What matters most is that you can speak credibly with senior lawyers, understand their commercial and practical pressures, and turn strong conversations into long-term client relationships. You will work directly with SideLight’s founders and leadership team, with significant influence over our commercial strategy, positioning and growth.
Reasons to use Rodeo
Start with a chat, not a search bar
Grad scheme, placement, apprenticeship? Not sure what you want yet — that's fine. Your agent talks it through with you and turns "I have no idea" into a shortlist.
It searches the market for you
Every day your agent scans the market matching roles against what actually matters to you, not just keywords on a CV.
Only hits
No noise. No "maybe this fits." Just roles with a clear explanation of why they're right — and where to focus when applying.
What you will do
- Lead new business development across claimant law firms, insurers and other litigation stakeholders.
- Build relationships with heads of department, managing partners and other senior decision-makers.
- Run thoughtful, credible product demonstrations grounded in real legal workflows.
- Convert pilots and early interest into sustained firm-wide adoption.
- Help shape SideLight’s positioning, pricing and go-to-market strategy.
- Develop partnerships with relevant legal, clinical and industry organisations.
- Bring client insight directly into our product roadmap.
- Represent SideLight at conferences, roundtables and industry events.
- Build the commercial function as the company grows.
Who we are looking for
You will ideally be a former practising lawyer with experience in clinical negligence, although strong candidates from personal injury, insurance, litigation funding or closely related fields will also be considered.
You will likely have:
- A strong understanding of complex injury litigation and medical evidence.
- The credibility to engage senior lawyers as a peer rather than as a conventional salesperson.
- Commercial instinct and the confidence to create and close opportunities.
- The ability to explain sophisticated technology clearly and persuasively.
- A practical understanding of how law firms make decisions and adopt new ways of working.
- The energy and independence to thrive in an early-stage, fast-moving business.
- A genuine interest in improving the way legal services are delivered.
Get help with your application
Your very own career expert that helps elevate your application to the next level.
Previous sales experience is valuable, but it is not essential. We are more interested in judgement, relationships, curiosity and commercial ambition.
Why SideLight
SideLight is already being used on active clinical negligence and personal injury matters by leading UK firms.
You will join at a point where the technology is proven, client demand is growing and the opportunity to define a new category remains wide open.
This role offers:
- A senior position with direct access to the founders and board.
- Meaningful influence over company and product strategy.
- The opportunity to build a commercial function rather than inherit one.
- A fully remote working environment.
- Competitive salary and meaningful equity participation.
- The chance to apply your legal experience in a way that could change how an entire area of litigation operates.
Interested?
Please send us a CV or LinkedIn profile, together with a short note explaining why SideLight and why now.
“It took my CV and asked me questions relevant to understanding what kind of jobs to suggest for me. Suggestions were almost perfect. Jobs were exactly what I’ve been looking for.”
Jessica, London
Skills
Location