Channel Sales Performance Coach

The Block; Remote; GBP 80,000 - 100,000; Full time

Job summary

A leading tech company is seeking a Sales Enablement & Training Lead to design and deliver an empowerment strategy for Independent Contractors. This role focuses on creating engaging training content and managing a training calendar to support onboarding and product launches. The ideal candidate will have at least 5 years of experience in sales enablement and strong facilitation skills. This position offers the flexibility of remote work within the UK, along with benefits like medical insurance and flexible time off.

Benefits

Medical insurance

Flexible time off

Retirement savings plans

Continuous learning opportunities

Qualifications

• Minimum of 5 years of related experience in sales enablement or training.
• Strong instructional design and facilitation skills.
• Excellent stakeholder management capabilities.

Responsibilities

• Design and deliver a modern enablement strategy for Independent Contractors.
• Create engaging digital learning content and training materials.
• Manage a structured training calendar to support onboarding and product launches.
• Deliver interactive training and coaching for channel sellers.

Skills

Sales enablement

Instructional design

Stakeholder management

Analytical mindset

Job description

About Square

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together. So we expanded into software and started building integrated, omnichannel solutions — to help sellers sell online, manage inventory, offer buy‑now‑pay‑later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Role Overview

As a Sales Enablement & Training Lead, you will design and deliver a modern enablement strategy that helps our Independent Contractors move faster, sell smarter and feel supported at every step of the customer journey. This highly collaborative, field‑connected role requires strong facilitation skills, a structured approach to process, and the ability to translate complex information into simple, actionable guidance for sellers and their leaders. Reporting into the Channel Sales Lead, this role offers remote work within the UK.

Responsibilities

• Build and execute a high‑impact enablement strategy aligned with our go‑to‑market priorities.
• Create engaging, digital‑first learning content, including sales playbooks, messaging frameworks, competitive insights and process documentation.
• Manage a clear, structured training calendar that supports onboarding, product launches and ongoing capability development.
• Deliver interactive training and coaching for new and experienced channel sellers across the UK.
• Design and facilitate leadership programmes to strengthen Channel Sales Manager and Team Lead capability across coaching, performance leadership and team engagement.
• Equip channel sales leaders with practical frameworks and tools to run effective team meetings, workshops and 1:1s.
• Define and document clear, scalable sales processes that support positioning, pricing and how we bring Square’s solutions to customers.
• Partner closely with Channel Sales Leadership to embed enablement into day‑to‑day workflows, driving consistent adoption and improved seller performance.
• Simplify ways of working to reduce friction and enable sellers to focus more on customer outcomes.
• Align training and readiness plans to product launch timelines in partnership with Product and Marketing teams.
• Translate new features and updates into compelling, easy‑to‑use training experiences that ensure sellers are fully launch‑ready.
• Gather feedback from sellers and leaders to continuously refine content, delivery and programme effectiveness.
• Use performance data and insights to measure impact, identify gaps and drive ongoing optimisation, including the use of automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws.

Qualifications

• Minimum of 5 years of related experience in sales enablement, sales training, sales leadership or a related field‑ideally within a high‑growth or channel‑driven environment.
• Strong instructional design and facilitation capability, with a track record of creating training that is practical, engaging and easy to adopt.
• Demonstrated ability to simplify complex information into clear processes, frameworks and messaging.
• Excellent stakeholder management skills and experience partnering across Sales, Product and Marketing.
• Analytical mindset – comfortable using data and feedback to inform decisions and improve programmes.
• Confident communicator, able to lead high‑quality training both virtually and in person.
• Nice to have: experience within fintech, payments or POS; familiarity with UK SME sales cycles; experience supporting field‑based, independent or channel sales teams.

Benefits

• Remote work within the UK.
• Medical insurance, flexible time off, retirement savings plans and modern family planning options.
• Access to Square’s global product suite and continuous learning opportunities.