Head of Sales

About us
Every large organisation runs on a web of legal entities, and the data behind them is scattered across in-house teams, law firms and accountants in PDFs, spreadsheets and slide decks. Jigsaw brings it into one place.
We started by giving lawyers and accountants a faster way to model client structures, and became the category leader doing it. Today 240+ organisations use Jigsaw, including all 10 of the world’s top 10 accountancy firms. Now we’re building Entity Lifecycle Management: one live record for every entity, from formation to dissolution.
Founded by former lawyer and repeat founder Stephen Scanlan, and backed by Exor Ventures.

Why join us:
You’ll help define a new software category with the backing of a loyal, global customer base. We hire people with high ownership and a bias for action, then trust them to do their best work.

About the role

As Jigsaw’s Head of Sales, you’ll level up a sales team that have been instrumental in establishing us as a market leader, whilst also preparing for a new challenge - building the go-to-market for a software category that doesn’t exist yet.

Across the corporate advisory network, lawyers, tax advisors and financial backers are all working off different versions of the same data, with no shared workspace, auditable source of truth, or easy to enact visual planning tools. This creates costly mistakes, messy handoffs and manual entry that general AI doesn't have the precision to automate. You’ll have ownership of how we launch and scale this, with no playbook to inherit.

Our existing customer base and revenue stream gives us the financial security to do this, where you’ll operate at a startup's pace with freedom to experiment. You'll shape the product roadmap with our Head of Engineering and partner directly with our CEO on strategy, whilst remaining hands-on with the sales team. With a global customer base, from the UK and Europe, through to the US, and APAC, there's genuine scope to travel and build relationships in person.

To be successful, we’d value someone bringing prior experience selling into both complex enterprise customers, whilst concurrently being comfortable building the motion for the SMB and mid-market, with industry experience across ERP, contract management, compliance, cyber security, or payments. Equally important is the mindset: this is a 0-to-1 journey, and we're looking for a genuine builder, someone energised by the process of creating something from nothing, not just by hitting a number, with the resilience to handle a go-to-market that will keep evolving as the product does.

You'll get to...

• Own and evolve Jigsaw's sales strategy, building on our existing outbound engine whilst designing the go-to-market for sales across multiple segments, from SMB to Enterprise

• Build with a startup's freedom and a scale-up's financial backing

• Nurture, mentor, and grow our existing sales team, adding enterprise capability without resetting what already works

• Shape the product roadmap with our Head of Engineering

• Partner directly with our CEO on Sales Strategy, ensuring we’re segmenting our markets correctly and impacting our customers in the right way

• Build long-term relationships with General Counsel, Heads of Legal Operations, and senior fincorp stakeholders across a global customer base with an opportunity to travel

• Create a flywheel between early wins and reference customers on both sides of the market, advisor and fincorp, to open up adjacent opportunities

You'll need...

• A strong track record in B2B enterprise SaaS sales, selling specifically into legal tech, legal operations, financial services or the broader professional services technology market

• Experience scaling company revenue from $15M +

• A track record building long sales cycles and long-term account relationships, not just closing transactional deals. You bring a little black book of contacts that you’d be happy contacting on day one

• Sales leadership or player-coach experience - you've hired, ramped, and coached teams of around 5+ people before. Equally strong: someone currently leading an SMB or scale-focused team who proved themselves on enterprise accounts earlier in their career

• Prior experience building a go-to-market strategy, you’re commercially focused and comfortable owning the numbers

• An analytical, data-led approach to sales efficiency - testing and experimenting rather than sticking to habit

• HubSpot experience, and you’re comfortable utilising it for workflows and reports, not just filling in fields.

• Genuine fluency with AI, and enthusiasm for pushing that further in how you sell and lead

• Gravitas and charisma, you’re credible in front of General Counsel and C-suite buyers, and clear, energising, and inspiring with your own team

• High ownership balanced with genuine collaboration

Nice-to-haves

• Familiarity with Entity Management Systems, contract lifecycle management, or adjacent legal/compliance software categories

• Experience leading Marketing, specifically for taking a product to market

• Experience selling in a marketplace or platform business model with a flywheel sales motion

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