Head of Sales

About Cledara Cledara is a platform for finance teams that gives visibility of your organization's software stack, provides data and insights to cut excess spend, and streamlines software-related admin. Now you have a detailed view of your software spending, you can see which tools are being used and where you could cut spend, painlessly. We don’t stop at savings, managing purchases and renewals is easy with simple workflows for requesting and approving new tools. Finally, with payments for software built-in, you have controls to ensure application owners can manage payments while you keep control with spend limits and budgets. We’ll even capture the invoices automatically, match them to payments, and sync with Netsuite, Xero and Quickbooks. Software is one of your biggest expenses, now you have the tools to reduce that expense by 30% and save 20 hours a month on admin. With 1000+ customers and offices in New York, London, and Barcelona, Cledara is all companies need to manage their software and AI. Visit our website to see our product and open roles.

Cledara

One place to manage all your software subscriptions

SaaS ManagementSoftware managementVirtual cardsand Fintech

See all employees

C

cledara.com

51-200 employees

Financial Services

New York, NY

2018

Privately Held

20k LinkedIn followers

Raised $24.3M

• 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.
• 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.
• 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.
• 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.
• 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
• 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.

• Training and development budget
• Annual leave
• Private medical insurance
• Corporate ClassPass account
• Onsite gym
• Apple MacBook