Head of Sales

Cledara; Greater London; On-site; GBP 120,000 - 180,000; Full time

Benefits offered by this job

Training budget

Annual leave 25 days

Private medical insurance

ClassPass access

Onsite gym

Company MacBook

Vibrant office near Spitalfields

Job summary

Cledara is seeking a Head of Sales in London to lead nine full-cycle Account Executives and an established Revenue Operations function. You will mentor AEs, refine sales execution, and build a high-performing team designed to scale, driving outbound motion and coaching across opportunities.

The role involves partnering with Product, Marketing and Customer Success to ensure alignment, optimize pipeline, and translate buyer objections into product iterations. Competitive compensation is offered.

Qualifications

• Proven B2B SaaS sales leadership with experience scaling outbound teams.
• Experience selling to SMB and lower mid-market buyers (Finance/IT/Operations personas).
• Player-coach who improves rep performance through coaching and deal management.
• Analytical, data-driven approach with RevOps collaboration for forecasting and funnel analytics.
• Interest in AI products and launching new offerings.

Responsibilities

• Lead and coach nine full-cycle Account Executives and RevOps functions.
• Elevate sales execution, coaching, and pipeline quality.
• Own forecast accuracy, funnel analytics, and CRM hygiene.
• Align with Product, Marketing, and CS on feedback loops for new AI products.

Skills

B2B SaaS Leadership

SMB & mid-market sales

Coaching & mentoring

Sales process & analytics

AI product interest

Spend management experience

Tools

CRM systems

Forecasting tools

Job description

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

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

• 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.