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Head of Sales

Jigsaw· Client
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Hybrid (London)Full-timePosted 4w ago

About the role

Head of Sales responsible for owning and evolving Jigsaw's sales strategy, building go-to-market across multiple segments (SMB to Enterprise), mentoring the sales team, shaping the product roadmap, and partnering with the CEO on strategy. Role involves leading complex enterprise sales, building SMB/mid-market motion, and scaling revenue with a startup-like pace.

Responsibilities

  • Own and evolve Jigsaw's sales strategy, building on the existing outbound engine and designing the go-to-market for multiple segments from SMB to Enterprise
  • Build with startup freedom and scale-up backing
  • Nurture, mentor, and grow the existing sales team, adding enterprise capability without resetting what already works
  • Shape the product roadmap with the Head of Engineering
  • Partner directly with the CEO on Sales Strategy, ensuring correct market segmentation and impactful customer engagement
  • Build long-term relationships with General Counsel, Heads of Legal Operations, and senior fincorp stakeholders across a global customer base with travel opportunities
  • Create a flywheel between early wins and reference customers (advisor and fincorp) to open up adjacent opportunities

Qualifications

  • Strong track record in B2B enterprise SaaS sales, selling into legal tech, legal operations, financial services or broader professional services tech markets
  • Experience scaling company revenue from $15M+
  • Proven ability to build long sales cycles and long-term account relationships; existing network of contacts
  • Sales leadership or player-coach experience (hiring, ramping, coaching teams of 5+) or SMB/scale-focused leader with enterprise background
  • Experience building go-to-market strategy, commercially focused with ownership of numbers
  • Analytical, data-led approach to sales efficiency; experimentation mindset
  • HubSpot experience with ability to use for workflows and reports
  • Fluency with AI and enthusiasm for leveraging it in selling and leadership
  • Gravitas and charisma to engage General Counsel and C-suite; clear, energising team leadership
  • High ownership balanced with genuine collaboration

Skills

Required:B2B enterprise SaaS salesGo-to-market strategy developmentTeam leadership and coachingData-driven salesHubSpotAI fluency
Last updated Oct 8, 2026. Interested? Apply on the company site.

About Jigsaw

Visual intelligence platform for professional diagramming

Transform complex business data into powerful visuals with visual intelligence. Create diagrams, timelines, and org charts 60x faster than PowerPoint. Trusted by 200+ firms.

visual intelligencediagrammingtimelinesorg charts
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