Location - Kings Cross, London - 4 days in the office per week

We’re looking for a dynamic and commercially-minded Head of Sales Enablement to lead the enablement function at Checkatrade during a pivotal phase of our commercial transformation.

As we shift from a transactional sales model to a strategic, value-led approach, you’ll play a critical role in designing and delivering the programmes, tools, and coaching that empower our sales and account management teams to succeed. You’ll partner closely with Sales Leadership, Product, Marketing, and Revenue Operations to ensure our teams have the knowledge, skills, and processes to drive revenue growth, improve conversion rates, and deliver an exceptional customer experience.

This is a unique opportunity to build the enablement function in a high-impact, high-visibility role where you’ll help shape how Checkatrade goes to market.

You’ll be accountable for delivering and improving outcomes that directly affect Checkatrade’s Sales team performance, including building a Sales bootcamp training, a framework to coach the team effectively, and building ongoing content to always upskill the sales team

• Defining the structure, standards, and metrics of a function that’s evolving from patchy manual execution to commercially powered scale

• Building a culture of accountability, clarity, and ownership across teams

• Owning the data, insights, and performance infrastructure that drives day-to-day outcomes and long-term strategy

• You’ll be expected to operate with full ownership, balancing short-term performance with long-term strategic bets, and regularly presenting plans and insights to leadership

What You’ll Be Doing

Enablement Strategy & Leadership

• Define the enablement vision and roadmap to support Checkatrade’s commercial strategy and sales transformation.

• Work with commercial leadership to identify capability gaps and prioritise enablement initiatives that drive measurable impact.

• Build and lead an enablement team to deliver high-quality programmes and resources.

Programme Design & Delivery

• Design and roll out onboarding programmes for new sales and account management hires, ensuring fast ramp-up times and strong foundational knowledge.

• Develop ongoing learning initiatives to improve selling skills, commercial acumen, product knowledge, and pipeline management.

• Create training that supports key transformations, e.g. moving from transactional selling to value-led conversations, implementing Sandler (or similar frameworks), and improving forecasting discipline.

Sales Process & Playbooks

• Partner with sales leadership and revenue operations to define and document scalable sales processes, playbooks, and best practices.

• Standardise discovery, pitch, objection handling, and negotiation approaches across teams.

• Embed clear processes to support pipeline hygiene, deal reviews, and forecasting accuracy.

Tools & Content Management

• Ensure sales teams have access to the right tools, assets, and content to support every stage of the sales process.

• Work with Product Marketing to develop competitive messaging and value propositions tailored to key customer segments.

• Maintain an enablement library with easy-to-find, up-to-date resources.

Coaching & Performance Support

• Drive a coaching culture by enabling managers to coach effectively and consistently.

• Analyse performance data and feedback to identify areas for targeted coaching or training interventions.

• Act as a trusted partner to sales leadership, providing insights and recommendations to improve performance.

Measurement & Impact Tracking

• Define KPIs and success metrics for all enablement programmes.

• Track enablement impact on core commercial metrics such as win rates, conversion rates, average deal size, and time to ramp.

• Continuously refine programmes based on data, feedback, and business needs

What You Bring

• Significant experience (typically 7+ years) in Sales Enablement, Sales Operations, Sales Leadership, or similar roles, ideally in high-velocity sales environments or marketplace businesses.

• Proven success designing and delivering enablement programmes that drive measurable improvements in sales performance.

• Strong understanding of B2B sales methodologies and processes, including pipeline management, sales forecasting, and value-based selling.

• Ability to translate business strategy into practical enablement initiatives.

• Exceptional communication and facilitation skills.

• Experience working cross-functionally with Sales, Marketing, Product, and Operations teams.

• Highly organised, with excellent project management skills and attention to detail.

• Data-driven, with the ability to measure programme effectiveness and ROI.

What You’ll Need to Be Successful in This Role

• A transformation mindset — comfortable challenging the status quo and designing programmes to support major shifts in how we sell.

• A deep understanding of how to move sales teams from transactional behaviours to structured, value-led selling.

• Practical experience building enablement materials, running workshops, and coaching teams through significant change.

• Ability to simplify complex processes into clear, actionable guidance for sales teams.

• Confidence operating in a fast-paced, evolving environment with shifting priorities.

• Collaborative style — skilled at building trust and influencing stakeholders at all levels.

• Passion for helping others succeed — driven by developing people and improving commercial outcomes.

• A proactive, hands-on approach with a bias for execution and measurable results.

About us

We’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.