Head of Sales

About us

At Jigsaw, we’re on a mission to transform the way professional services and financial institutions work. We do this by helping our clients organise, visualise and use their data (think Figma or Canva but for the ‘City’). Our clients include the world’s biggest consultancies, leading financial institutions and top law firms. Jigsaw was founded by two seasoned entrepreneurs, Stephen and Travis. This is their second venture together; their first was acquired by a US private equity firm and went on to become a billion-dollar company and a household name in professional service firms across the world. Jigsaw is now on a growth trajectory few Series A companies achieve - putting us in the top quartile SaaS companies globally. Today we proudly serve thousands of users from nearly two hundred businesses worldwide, who love our products and use them every day. But we’re only getting started! We have ambitious goals and we’re looking for talented people to help us achieve them.

Why join us?

We're not about the corporate grind; instead, we thrive on creativity, enthusiasm, and a touch of humour to make magic happen. We hire people with high ownership and a bias for action. Then we trust and empower 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 complex enterprise, multi stakeholder purchase categories - think ERP, contract management, compliance, cyber security, or payments. You’ll also need to roll up your sleeves and work with the sales team, join their calls, run demos with clients and demonstrate what good looks like.

You'll get to...

• Own and evolve Jigsaw's enterprise sales strategy, building on our existing outbound engine while designing the go-to-market for larger, more complex deals
• Shape enterprise selling for a brand-new category, our ELM platform, with real ownership from day one
• 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 5+ people before
• 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