Head of Sales

One Way Ventures; Greater London; On-site; GBP 120,000 - 190,000; Full time

Benefits offered by this job

Competitive compensation with equity

Comprehensive health insurance

Gym & wellness reimbursement

Work from anywhere for up to 4 weeks a

Generous vacation policy, duvet days,

Job summary

Easyship in London is seeking a Head of Sales (Player/Coach) to lead and grow the enterprise sales team, owning performance, coaching, and the execution of high-value deals. You will drive quota attainment and refine the GTM playbook while partnering with marketing, RevOps, and sales leadership to optimize pipeline.

Ideal candidates bring 6+ years of B2B SaaS/logistics sales experience, a proven track record of coaching AEs to win complex multi-stakeholder deals, and strong analytical

Qualifications

• 6+ years of B2B sales experience.
• 3+ years managing an enterprise sales team.
• Experience in SaaS or logistics is preferred.
• Experience building and refining a repeatable enterprise GTM sales process.
• Data-driven mindset with strong forecasting skills.

Responsibilities

• Leading, coaching, and developing a team of enterprise Account Executives, owning their ramp, performance, and career growth.
• Driving the team to hit and exceed pipeline and revenue targets on large, complex, multi-stakeholder deals.
• Refining and enforcing the enterprise GTM playbook — qualification, deal strategy, MEDDIC (or equivalent), messaging, and negotiation.
• Coaching reps through complex sales cycles, navigating procurement, legal, and C-level stakeholders to close.
• Running disciplined pipeline reviews, accurate forecasting, and clear reporting on team performance to leadership.
• Partnering with marketing, RevOps, sales engineering, and sales leadership to optimize pipeline, territory design, and the overall funnel.
• Using data to diagnose performance gaps, coach to specific behaviors, and continuously improve team productivity.
• Hiring, onboarding, and scaling the enterprise sales team as Easyship grows.
• Staying informed about market dynamics and competitor activity to help Easyship maintain a competitive edge.

Skills

B2B sales

Enterprise sales management

SaaS / logistics knowledge

Data-driven

Forecasting

Global team management

Coaching & collaboration

Communication skills

Resilience & self-motivation

Ambiguity tolerance

Job description

About Easyship:

Easyship is one of the world's leading multi-carrier shipping software, built to make global eCommerce borderless. Since 2014, we've been on a mission to democratize logistics by removing the "black box" of international shipping costs and complexities. Trusted by over 100,000 brands, our platform provides a single "mission control" for global trade, offering access to 550+ courier services across 200+ destinations.

We are an award-winning, global team (Forbes 30 Under 30, TechInAsia's Best Startup) with offices in London, New York, Hong Kong, and beyond. We're growing fast, we value transparency, and we genuinely enjoy building the infrastructure that powers modern commerce. If you're ready to solve complex problems at scale, we'd love to have you join us.

Job Title: Head of Sales (Player/Coach)
Location: London
Reporting to: Director, Commercial & Marketing.
Key Relationships: Sales Team, Customers, Marketing, Customer Service.

Who We're Looking For:

Easyship is a shipping technology platform that connects sellers and marketplaces to couriers, and we build customized end-to-end logistics solutions for the world's fastest-growing brands. As we move upmarket, our enterprise sales team is closing larger, more complex deals, and we need a leader to drive it. We're looking for a Sales Manager to lead a team of enterprise Account Executives, owning their performance, coaching, and execution against high-value, multi-stakeholder deals. We're after a player-coach who knows eCommerce and shipping, has carried and led enterprise quota, and gets energy from developing reps and sharpening the GTM motion.

What would you be responsible for:

• Leading, coaching, and developing a team of enterprise Account Executives, owning their ramp, performance, and career growth.
• Driving the team to hit and exceed pipeline and revenue targets on large, complex, multi-stakeholder deals.
• Refining and enforcing the enterprise GTM playbook — qualification, deal strategy, MEDDIC (or equivalent), messaging, and negotiation — to improve win rates and deal sizes.
• Coaching reps through complex sales cycles, navigating procurement, legal, and C-level stakeholders to close.
• Running disciplined pipeline reviews, accurate forecasting, and clear reporting on team performance to leadership.
• Partnering with marketing, RevOps, sales engineering, and sales leadership to optimize pipeline, territory design, and the overall funnel.
• Using data to diagnose performance gaps, coach to specific behaviors, and continuously improve team productivity.
• Hiring, onboarding, and scaling the enterprise sales team as Easyship grows.
• Staying informed about market dynamics and competitor activity to help Easyship maintain a competitive edge.

You Might Be a Good Fit If:

• You have 6+ years of B2B sales experience, including 3+ years managing an enterprise sales team, preferably in SaaS or logistics.
• You have a track record of consistently hitting team quota and developing AEs into top performers on complex, high-value deals.
• You have understanding and experience with eCommerce shipping, warehousing, and fulfillment logistics.
• You have experience building and refining a repeatable enterprise GTM sales process in a metrics-driven environment.
• A "Data-First" approach and strong analytical and forecasting skills.
• You have experience in managing a global team
• You are skilled in coaching, influencing, and collaborating with distributed global teams.
• You have excellent organizational, verbal, and written communication skills.
• You possess resourcefulness, resilience, and self-motivation, and you thrive in ambiguity within a fast-paced, entrepreneurial environment with high expectations.

The Way We Work:

• Ownership: You take responsibility for outcomes, not just tasks
• Collaboration: You share context and move forward together
• Resilience: You adapt quickly and keep momentum
• Integrity: You operate with honesty and transparency
• Diversity: You value different perspectives
• Initiative: You take action and learn by doing
• Growth mindset: You seek feedback and continuously improve

Why You’ll Love Working at Easyship?

• Competitive compensation with equity options
• Comprehensive health insurance
• Gym & wellness reimbursement
• Work from anywhere for up to 4 weeks per year
• Generous vacation policy, duvet days, and mental health days

What's it like working in sales? Hear directly from our team.

Headquartered in London with offices in New York, Hong Kong, Singapore, Melbourne, Toronto, and Taipei – our team is global and growing.

Easyship is an equal opportunity employer. We make all employment decisions- recruiting, hiring, pay, benefits, training, promotion, leave, and separation based on qualifications, merit, and business needs. We do not discriminate on the basis of race, colour, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, veteran or military status, citizenship, or any other characteristic protected by law.