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About the Role

Square is seeking a Sales Coaching & Training Manager to drive real results across channel sales teams. This hands-on role involves coaching sales teams in the field and on the phone, identifying performance gaps, and building scalable content and programs. The ideal candidate is a builder who thinks commercially, uses data to find gains, and requires minimal direction.

Responsibilities

• Coach Independent Contracts 1:1 in the field and on the phone, providing real-time feedback to improve conversion, deal quality, and activation rates.
• Support RSMs in activating new ICs faster through improved onboarding training and regular reporting.
• Utilize performance data to identify and prioritize coaching efforts for lowest and highest performers.
• Deliver training and coaching for new and experienced channel sellers to shorten ramp time and increase productivity.
• Coach Channel Sales Managers directly and run leadership programs to improve team output.
• Own the Regional Sales Managers (RSM) Training & Certification program.
• Manage a structured training calendar aligned with commercial priorities, including onboarding, product launches, and capability gaps.
• Collaborate with Learning Experience Designer and AI tools to produce sales playbooks, value selling frameworks, competitive insights, and process documentation.
• Document clear, scalable sales processes for positioning and pricing.
• Align training and readiness plans with Product and Marketing for seamless product launches.
• Provide Channel Sales Managers with tools to run effective team meetings and 1:1s.
• Partner with Channel Sales Leadership to embed enablement into daily workflows.
• Track and report on the commercial impact of coaching and programs, using data to refine strategies.
• Be accountable for the connection between enablement work and channel sales performance.

Requirements

• 5+ years in sales coaching, sales enablement, sales training, or similar, ideally in a high-growth or channel-driven environment.
• Proven track record of moving performance metrics, not just delivering training.
• Real field coaching experience with direct salesperson development and measurable results (conversion, deal size, ramp time, retention).
• Builder mindset with a commercial edge, capable of creating structure and programs from scratch and measuring success by produced numbers.
• Strong content design and facilitation skills with usable training that impacts performance.
• Ability to translate complex information into clear, simple frameworks and messaging.
• Strong stakeholder management skills, particularly across Sales, Product, and Marketing.
• Analytical mindset, comfortable with performance data, identifying gaps, and proving impact.
• Confidence and credibility in the field, earning trust and serious consideration from sellers and leaders.
• Experience with fintech, payments, or POS is a plus.
• Familiarity with UK SME sales cycles is a plus.
• Experience with field-based, independent, or channel sales teams is a plus.

Skills

• Sales coaching
• Sales enablement
• Sales training
• Content design
• Facilitation
• Stakeholder management
• Analytical skills
• Performance data analysis
• Field coaching

Location

• Remote within the UK
• Regular field travel

Work Type

• Remote
• Field travel

Experience Level

• 5+ years

Benefits

• Remote work
• Medical insurance
• Flexible time off
• Retirement savings plans
• Modern family planning

About the Company

• Block, Inc. builds technology to increase access to the global economy.
• Square makes commerce and financial services accessible to sellers.
• Cash App is the easy way to spend, send, and store money.
• Afterpay is transforming the way customers manage their spending over time.
• TIDAL is a music platform that empowers artists to thrive as entrepreneurs.
• Bitkey is a simple self-custody wallet built for bitcoin.
• Proto is a suite of bitcoin mining products and services.
• Together, we’re helping build a financial system that is open to everyone.

Equal Opportunity

• We may use 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.
• Contact us here with hiring practice or data usage questions.