- Base
- Not disclosed
- OTE
- Not disclosed
- Posted
- 8d ago
Still open · checked 17h agoon Cledara's careers page
The job
- What you'd do
- Lead nine salespeople who sell tools that cut wasted software costs to small and mid-size businesses, mainly finance and IT leaders. Based in London, four days a week in the office.
- What you'd sell
Shows companies their software bills and cuts wasted spend
When a company has to keep track of the software its staff pays for, it usually digs through bills and login lists by hand. The problem is, unused tools and duplicate apps quietly eat money every month. Cledara shows finance and IT leaders every subscription in one place and cuts the waste, so the company stops paying for software nobody uses.
In plain English, from their own job posts. Something wrong? Tell me · More Finance & payments companies →
- Who you'd sell to
- Finance and IT leaders at small businessesIn their words: “We give finance and IT leaders complete visibility into their subscriptions, eliminate wasted spend on unused seats and redundant tools, and automate administrative tasks.”
- Where deals come from
- Not stated in the posting.
The Braun Read
Proceed with cautionA few things here deserve a hard look before you spend time on it.
- Pay
- No pay listed at all.
- Transparency
- Says nothing about quota, attainment, deal size, territory or sales cycle. Ask about all five.
- Time on market
- Open 8 days.
- Company hiring
- 2 sales roles open, hiring at a steady pace.
Red lights
- Pay. No pay listed at all.
Yellow lights
- Leads a team and sells. You'd lead a team and work deals yourself. Ask whether you carry a personal quota and how your pay splits between the two.
Green lights
None spotted.
Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.
Questions to ask on the first call
Built from what this posting leaves out. How they answer tells you as much as what they say.
- 1.
How is time split between managing the team and carrying your own number?
Two jobs, one paycheck. Find out which one wins when time runs out.
- 2.
What percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.
- 3.
What are the base and the OTE for this role?
No point investing hours before you know the number.
- 4.
What's the annual quota, and how was it set?
A quota built from real data is a target. Otherwise it's a hope.
- 5.
Where does pipeline come from: inbound, SDRs, or me?
Before You Apply
Find out where you fit, and where you don't, before you hit submit.
Why I built it this way ↓
Most résumé tools try to make you look like a match. I'd rather help you find out if you are one.
Nothing made up.
Nothing goes on your résumé that you didn't do. If a line would need a number you didn't give me, I ask. I don't guess. On Braun Board it's checked in code, not just promised.
Curiosity before conclusions.
If the job wants something your résumé doesn't show, I ask before I assume. Plenty of sellers have done the thing and just never wrote it down.
Sorting, not selling.
Some jobs won't line up with what you've done. Finding that out before you apply isn't a loss. It's an hour back, spent on a job that fits.
No score.
A match score tells you how well you copied their words. It doesn't tell you whether you'd be good at the job, or happy there.
It's the same way I teach selling. We don't control who says yes. We do control where we spend our time, and whether everything we say is true.
Josh
More on this1 Is the job worth it?
Proceed with caution. A few things here deserve a hard look before you spend time on it.
- No pay listed at all.
Might be worth asking about this before you spend an hour on a tailored résumé.
See the full Braun Read2 Where you fit
Upload once, see where you fit on any job.
Sign in and add your résumé. I'll show you where you line up, ask before I assume, and never add anything you didn't do.
Sign in →What people say about working at Cledara ↓
Got an offer from Cledara? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh
Rather talk it through? Call or text me: 954-695-0844 (text)
Full posting
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
This is a London-based role requiring 4 days per week in the office.
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.