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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’ve 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.
Today, we are a partner to sellers of all sizes - large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.
The Role
Square helps small businesses do business - operating more efficiently, selling confidently, and finding new opportunities. As our indirect sales channel scales, we need a Sales Coaching & Training Manager who drives real results across our channel sales teams, not just training volume.
This is a hands-on role. You'll be in the field and on the phone with Independent Contractors and Channel Sales Managers - spotting performance gaps, coaching in the moment, and pushing people to do better. You own the numbers, not just the calendar. You'll also build the content and programs that scale what works across the team (and other markets).
We need a builder who thinks commercially - someone who creates structure from scratch, uses data to find where the biggest gains are, and gets on with it without needing much direction. You'll work with our Learning Experience Designer and AI tools to speed up content creation, so more of your time goes into coaching, not producing.
Reporting into the Head of Sales Enablement, with dotted line to Head of UK Sales. Remote within the UK, with regular field travel.
What you'll do
Coaching - driving field performance
- Coach Independent Contracts 1:1 in the field and on the phone - joining merchant visits, shadowing their day-to-day, and giving real-time feedback that lifts conversion, deal quality and activation rates
- Support RSMs in activating new ICs faster - improving onboarding training, and building regular reporting and tracking so we can spot performance issues early and act on them
- Use performance data to identify your lowest and highest performers, and prioritize your coaching time where it will move the numbers most
- Deliver training and coaching for new and experienced channel sellers that shortens ramp time and gets new starters to full productivity faster
- Coach Channel Sales Managers directly, and run leadership programs that improve their team's output, not just their own
Programs & content building - built to convert
- Own the Regional Sales Managers (RSM) Training & Certification program, making sure every RSM is properly trained and certified, and kept up to date on a regular basis
- Own a structured, reliable training calendar tied to commercial priorities - onboarding, product launches and the capability gaps costing us revenue today
- Work with our Learning Experience Designer and AI tools to produce sales playbooks, a value selling framework, competitive insights and process documentation that sellers actually use to close more, not just training for training's sake
- Document clear, scalable sales processes for positioning and pricing that make it easier for sellers to win deals
- Align training and readiness plans with Product and Marketing so sellers are fully productive from day one of a launch, not weeks behind
Driving adoption & impact - owning the outcome
- Give Channel Sales Managers practical tools to run team meetings, workshops and 1:1s that translate into better team results, not just better-run meetings
- Partner with Channel Sales Leadership to embed enablement into everyday workflows so it shows up in the numbers, not just in a training log
- Track and report on the commercial impact of your coaching and programmes - conversion, activation, ramp time, retention - and use that data to double down on what's working and cut what isn't
- Be accountable for the connection between your enablement work and channel sales performance - this role is measured on results, not activity
You have
- 5+ years in sales coaching, sales enablement, sales training or similar - ideally in a high-growth or channel-driven environment, with a track record of moving performance metrics, not just delivering training
- Real field coaching experience - you've actually developed salespeople directly and can point to the results it drove (conversion, deal size, ramp time, retention)
- A builder mindset with a commercial edge - you've created structure and programmes from scratch, and you judge success by the numbers they produced
- Strong content design and facilitation skills, with training you've built that sellers actually use and that shows up in performance data
- The ability to turn complex information into clear, simple frameworks and messaging that sellers can apply immediately
- Strong stakeholder management, especially across Sales, Product and Marketing
- A genuinely analytical mindset - you're comfortable in performance data, spotting the gaps that matter and proving impact after the fact
- Confidence and credibility in the field - sellers and leaders trust you quickly and take your feedback seriously
- Nice to have: fintech, payments or POS experience; familiarity with UK SME sales cycles; experience with field-based, independent or channel sales teams
Application Guidelines
Candidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed.
Use of AI in Our Hiring Process
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.
Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering. Check out our other benefits at Block.
Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. 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.
