The Company

Cledara helps companies manage their software and AI spend. We give finance and IT leaders complete visibility into their subscriptions, eliminate wasted spend on unused seats and redundant tools, and automate administrative tasks.

Backed by tier-1 SaaS and fintech investors—including Notion Capital, Nauta Capital, Anthemis, and CommerzVentures—Cledara supports over 1,300 customers across 32 countries. We have established product-market fit, high retention, and top-ranked usability (recognised among the Best UK Software Companies by G2).

We are now preparing to launch an autonomous software-management agent, moving from passive management to proactive optimization. To drive this next growth phase, we are hiring a hands-on, high-tempo Head of Sales.

The Role

Reporting to the COO and Co-founder, you will lead nine full-cycle Account Executives and an established Revenue Operations function.

This is a role with a licence to challenge and build, not just maintain. You will be tasked with elevating execution, optimising pipeline conversion, and architecting a scalable revenue machine.

Our sales team runs an effective outbound motion that generates a strong, consistent pipeline. In this role, your focus will be on mentoring AEs, refining sales execution, and building a high-performing team designed to scale. This is a frontline leadership position suited to someone who thrives on coaching, navigating live opportunities, and participating in customer conversations. The role carries no individual sales quota; variable compensation is linked directly to team performance.

Your Key Responsibilities include

Deal Execution & Sales Coaching

• Drive consistent quota attainment through structured training, active deal support, and rigorous performance management.
• Coach and upskill nine full-cycle Account Executives across the entire sales cycle—from initial discovery through to commercial negotiation and closing.
• Run disciplined deal inspections, objection-handling workshops, and call-shadowing sessions to boost win rates and shorten sales cycles.

Sales Operations & Revenue Architecture

• Lead the Revenue Operations function to enhance forecasting accuracy, funnel analytics, and CRM pipeline hygiene.
• Diagnose conversion bottlenecks across every stage of the funnel and implement pragmatic playbooks to resolve them.

Team Building & Performance Management

• Establish rigorous sales KPIs, pipeline coverage ratios, and transparent accountability frameworks across the floor.
• Retain strong performers and recruit additional AEs as the team grows.
• Attract, assess, and onboard top-performing AEs as the company expands.

GTM Strategy & Product Expansion

• Develop and test the sales motion for a forthcoming product as it moves towards general release
• Serve as the frontline feedback loop for Product, Marketing, and Customer Success, translating buyer objections into immediate product and messaging iterations.
• Collaborate closely with Customer Success and Product to identify opportunities and solve bottlenecks

Requirements

The ideal candidate will bring:

• Proven B2B SaaS Sales Leadership: Track record leading, coaching, and scaling 2 or more outbound sales teams within a fast-paced, venture-backed tech company.
• SMB Expertise: Proven success selling B2B SaaS solutions into SMB and lower mid-market buyers (ideally targeting Finance, IT, or Operations personas).
• A player-coach mentality: You know how to improve rep performance through practical coaching and effective deal management
• Process & Data Rigor: Analytical mindset capable of partnering with RevOps to diagnose conversion leakage, evaluate unit economics, and forecast accurately.
• AI Products: Genuine interest in AI and enthusiasm for bringing a new product to market
• Bonus: Prior experience in the spend management space

Benefits

• Competitive Compensation: A competitive salary package that reflects the impact you make on our growth engine.
• Direct Ownership: Work directly with company leadership to shape and scale how our revenue teams operate.
• Growth Opportunity: Your growth is based on results and the systems you build, not tenure.
• Training and Development: Cledara provides £500 annually for approved training and development.
• Annual Leave: 25 days of annual leave plus public holidays.
• Private Medical: Access to private medical insurance through BUPA.
• Health and Fitness: Access to a corporate ClassPass account, an onsite gym, and free entry to all gyms within the Fora network.
• Great Tech: Work with top tier hardware and software, including a company provided Apple MacBook.
• Vibrant Office: Our modern workspace is a stone's throw from Spitalfields Market, featuring an onsite gym, rooftop terrace, and a fully stocked kitchen with complimentary fruit, snacks, tea, and coffee.