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For Companies At a Glance
- Tasks: Lead the sales enablement function, designing programmes and coaching for sales teams.
- Company: Checkatrade is the UK's top platform for finding trusted tradespeople, with over 6 million reviews.
- Benefits: Enjoy a dynamic work environment in Kings Cross, with opportunities for growth and impact.
- Why this job: Shape the future of sales at Checkatrade while driving real change and improving customer experiences.
- Qualifications: 7+ years in Sales Enablement or similar roles, with strong B2B sales knowledge and project management skills.
- Other info: Join a fast-growing company with a passion for quality work and making a difference.
The predicted salary is between 48000 - 72000 £ per year.
This job is brought to you by Jobs/Redefined, the UK\’s leading over-50s age inclusive jobs board.
Join us as Head of Sales Enablement
Want to do work that really matters?
At Checkatrade, we\’re building the UK\’s go-to home improvement marketplace. Every day, we help millions of homeowners find the right tradesperson for the job, fast, fair, and without the faff.
As our next Head of Sales Enablement, you\’ll be front and centre in our commercial transformation, moving us from a transactional sales model to a value-led, insight-driven approach. You\’ll shape how our sales and account teams show up, sell better, and drive sustainable growth.
Forget long lists, here\’s what you\’ll actually spend your time on:
- Setting the enablement vision and building the team, programmes, and tools to deliver it.
- Creating onboarding, coaching, and learning programmes that actually move the dial.
- Equipping our teams with scalable playbooks, sharp messaging, and practical content that supports how we sell today (and how we need to sell tomorrow).
- Partnering with leaders across Sales, Product, Marketing, and RevOps to make sure enablement is embedded, effective, and evolving.
- Defining KPIs and tracking the real impact on win rates, conversion, ramp time, and deal value.
- Leading with insight, presenting strategy and performance to senior stakeholders, and always looking for ways to improve how we work.
It\’s not about ticking every box. It\’s about turning up curious, ready to crack on. You\’ll do well here if you bring:
- Long-standing involvement in Sales Enablement, Sales Ops, or Sales Leadership, ideally in high-growth or marketplace environments.
- A clear record of designing programmes that measurably improve sales performance.
- Practical experience leading teams through transformation, from transactional to value-led selling.
- Deep knowledge of B2B sales methods, pipeline and forecasting best practices, and how to support teams at every stage.
- Brilliant communication and facilitation skills, and a knack for simplifying the complex.
- Confidence working cross-functionally and influencing at all levels.
- A hands-on, proactive approach with a bias for execution and outcomes.
We believe great work deserves great rewards. Here\’s just a taste:
- Competitive salary + annual bonus
- Health, well-being and learning support
- Gym membership, Smart Tech Scheme and Cycle Scheme
- Birthday/Special day leave
- Buy & sell holiday scheme
- 1 week\’s paid charity leave and much more!
How we\’ll get to know each other:
- Screening call with one of our Talent Acquisition Partners
- 1st stage interview with our VP of Sales
- 2nd stage interview will be a case study with a panel
- 3rd stage interview will be with our COO and/or VP of Marketplace (Please note the 2nd and 3rd stage interviews may change order depending on our stakeholders\’ availability)
If you require any reasonable adjustments during our interview process, please discuss them with your Talent Acquisition Partner.
If this sounds like the place where you can do your best work, we\’d love to hear from you, even if you don\’t tick every box
About usWe\’re Checkatrade – the UK\’s leading platform for finding a tradesperson. With more than 50,000 trades listed and over 6 million reviews, we help homeowners get jobs done right and help tradespeople grow their business.
We\’re growing fast, with big plans to become the go-to brand for home improvements. If you care about great work, take pride in the details, and want to make an impact, you\’ll fit right in.
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Head of Sales Enablement employer: Checkatrade
Contact Detail:
Checkatrade Recruiting Team
StudySmarter Expert Advice 🤫
We think this is how you could land Head of Sales Enablement
✨Tip Number 1
Familiarise yourself with Checkatrade's current sales processes and methodologies. Understanding their existing framework will allow you to tailor your approach and demonstrate how you can enhance their transition to a value-led selling model.
✨Tip Number 2
Network with professionals in the sales enablement field, especially those who have experience in high-velocity sales environments. Engaging with industry peers can provide insights into best practices and trends that you can bring to Checkatrade.
✨Tip Number 3
Prepare to discuss specific examples of successful enablement programmes you've designed or implemented in the past. Highlight measurable outcomes to showcase your ability to drive performance improvements, which is crucial for this role.
✨Tip Number 4
Research the latest tools and technologies used in sales enablement. Being knowledgeable about innovative solutions can position you as a forward-thinking candidate who can help Checkatrade stay competitive in the market.
We think you need these skills to ace Head of Sales Enablement
Some tips for your application 🫡
Tailor Your CV: Make sure your CV highlights relevant experience in Sales Enablement, Sales Operations, or similar roles. Focus on achievements that demonstrate your ability to drive measurable improvements in sales performance.
Craft a Compelling Cover Letter: In your cover letter, express your passion for transforming sales processes and your understanding of value-led selling. Use specific examples from your past experiences to illustrate how you can contribute to Checkatrade's commercial strategy.
Showcase Your Leadership Skills: Emphasise your experience in building and leading teams. Highlight any successful enablement programmes you've designed and delivered, and how they impacted sales performance.
Demonstrate Data-Driven Decision Making: Include examples of how you've used data to measure programme effectiveness and refine strategies. This will show your analytical skills and your ability to track impact on key commercial metrics.
How to prepare for a job interview at Checkatrade
✨Understand the Sales Transformation
Make sure you grasp the shift from a transactional sales model to a value-led approach. Be prepared to discuss how your experience aligns with this transformation and how you can contribute to shaping the enablement function.
✨Showcase Your Programme Design Skills
Be ready to share examples of enablement programmes you've designed and delivered in the past. Highlight measurable improvements in sales performance that resulted from your initiatives, as this will demonstrate your capability in this area.
✨Emphasise Cross-Functional Collaboration
Since the role involves working closely with various teams like Sales, Marketing, and Product, be prepared to discuss your experience in cross-functional collaboration. Share specific instances where you successfully influenced stakeholders and drove results.
✨Prepare for Data-Driven Discussions
Familiarise yourself with key performance indicators (KPIs) relevant to sales enablement. Be ready to discuss how you have used data to measure programme effectiveness and make informed decisions in previous roles.
