Head of Sales

What You'll Do

Sales Leadership & Strategy

• Lead, develop, and hold accountable a high-performing sales organisation across New Business, Enterprise Account Management, Sage 200 and Sage Intacct Account Management, Sales Support, and Pre-Sales/Solution Architecture.
• Build a culture of accountability, collaboration, and continuous improvement — setting clear expectations, providing regular feedback, and empowering managers to lead with confidence and consistency.
• Coach and develop managers and individuals across all five sales sub-teams, actively assessing and upgrading talent to maintain a high-performance bar.
• Identify, develop, and retain high-potential talent; make clear decisions on underperformers when needed.
• Contribute as an active member of the Commercial Leadership Team, supporting the wider commercial strategy alongside Marketing and Lead Generation.

Revenue Operations & Process

• Lead the adoption of HubSpot as the sales system of record — embedding consistent sales processes, forecasting, pipeline management, and reporting across the organisation.
• Build scalable, data-driven sales processes from a standing start, with a focus on pipeline hygiene, funnel visibility, and forecasting discipline.
• Develop the New Business team (currently one player-manager and two contributors, growing to three) to build velocity in net new Sage Intacct, Sage 200, and Sage X3 logos and improve closure rates.
• Inherit a New Business motion that is approximately 70% marketing-fed and build a more balanced, proactive pipeline-generation engine over time.
• Formalise the reporting and go-to-market integration of the Pre-Sales/Solution Architect team within the broader sales structure.

Account Management & Retention

• Enhance Datel's proactive account management model, shifting the team from reactive to proactive through segmentation, tiering, cadence, and strategic account planning.
• Drive customer value, retention, and commercial growth across Sage Intacct, Sage X3, Sage 200, and Sage 1000 — ensuring in-life growth and migration conversations are built on long-term partnerships, not short-term transactions.
• Treat the Sage 500/1000 legacy migration wave (customers moving ahead of 2029 end-of-life) as a strategic account expansion lever.

Commercial & Strategic

• Contribute measurably to new-logo volume targets and recurring revenue growth, thinking in ARR, customer lifetime value, and EBITDA — not just top-line bookings.
• Build a cohesive, modern sales motion aligned to how buyers of financial software and services actually buy today.
• Anticipate the market's shift from time-and-materials to outcome/fixed-fee services pricing and position Datel ahead of the curve.
• Align sales plans and priorities with marketing activity, customer growth initiatives, and broader business objectives.

What They're Looking For

Required

• Proven sales leadership experience in a SaaS or recurring-revenue environment — fluent in ARR, recurring revenue, and customer lifetime value as operating metrics.
• Strong rev-ops orientation — naturally thinks in KPIs, pipeline data, and process; a builder, not just a closer.
• Demonstrated experience professionalising account management through segmentation, tiering, and shifting teams from reactive to proactive.
• Proven ability to build scalable sales processes and manage data flow and pipeline hygiene from a standing start.
• Strong people leadership — experience developing managers, building team capability, and making clear talent decisions.
• Commercially fluent, with the ability to quickly get up to speed on partner economics, channel dynamics, and margin-aware deal structuring.
• Data-driven by default: insists on pipeline visibility, forecasting discipline, and funnel reporting as standard practice.
• Growth mindset — a credible long-term leader as the business scales, not a hire for the moment.

Nice to Have

• HubSpot experience, including building workflows, reporting, and sales process automation.
• Experience with comp plan design and sales incentive structuring.
• Familiarity with the Sage partner ecosystem — though candidates sourced directly from the Sage business partner pool are not being considered for this role.
• Experience embracing AI and technology within sales processes, including research agents and AI transcription tools.