Head of Sales

Who you are

You are a builder at heart and passionate about sales. You thrive in dynamic environments, enjoy working closely with a team, and take ownership of driving business growth.

Traits, both common and defining, of the Head of Sales at WAY:

At WAY, sales is not just a function — it’s how we get to customer truth, validate business models, and build enduring revenue engines. Here’s how our values show up in this role:

• Customers are our obsession
  You go deep to understand customer pain and make sure our messaging, offers, and actions reflect that understanding.

• Everything is possible
  You turn challenges into experiments and setbacks into insights. You help teams find a path forward through creativity and persistence.

• Strength in diversity
  You work across different teams, business models, and customer types. You bring empathy and adaptability to how you communicate and lead.

• Grit
  You stay committed through long sales cycles and early rejections. You build and maintain momentum no matter the obstacles.

• Energy and execution
  You operate with urgency and discipline. You drive outreach, structure processes, and track toward goals with a bias for action.

• Curiosity enables potential
  You ask why deals are won or lost, what messages resonate, and how we can improve. You love learning from customers.

• Pragmatic about purpose
  You’re here to build sales systems that scale, not chase short-term wins. You care about lasting relationships, not just closing deals.

About the role

WAY is a company builder focused on launching and scaling technology-enabled businesses in Japan. As Head of Sales, you’ll support new business validation efforts, lead early customer development, and help build the sales playbooks for our growing companies.

You’ll work closely with founding teams and the WAY leadership to shape GTM strategies, generate early revenue, and help build high-performing commercial teams. This is both a strategic and hands-on role ideal for someone who thrives in ambiguity, leads with empathy, and executes with excellence.

What you’ll do

• Lead and support early-stage sales efforts across multiple companies and initiatives

• Conduct and coach customer discovery conversations to validate the problem, solution, and willingness to pay

• Develop early sales playbooks, scripts, objection handling, and pricing experiments

• Help design and implement CRM and sales systems to track pipeline, conversion, and customer feedback

• Hire, train, and manage early sales team members within portfolio companies

• Advise and collaborate on go-to-market strategy, segmentation, and channel development

• Bring customer insights back into product development and business model iteration

• Serve as a trusted thought partner to founders and cross-functional teams

How we work with AI

At WAY, we believe AI is not just a tool — it's a competitive edge. Everyone on the team, regardless of role, is expected to:

• Identify and automate parts of your job that can be made more efficient using AI.

• Experiment with AI tools to increase productivity, improve quality, and unlock new ideas.

• Share what you learn with your teammates so we all get better, faster.

Who we are looking for

• 5+ years of experience in B2B sales or go-to-market roles, with at least 2 years in a sales leadership or player-coach role

• Proven ability to build and lead early sales efforts from scratch

• Deep comfort with ambiguity, experimentation, and learning in real time

• Strong communication skills in both English and Japanese (or business-level in one and fluent in the other)

• Track record of coaching others and building repeatable systems that scale

• Entrepreneurial mindset with high standards, resilience, and a team-first mentality

• Strong strategic thinking paired with hands-on sales execution capabilities.

• Native-level Japanese proficiency and business-level English.