Director of Sales Strategy

Chowbus; Chicago (IL); On-site; USD 130,000 - 180,000; Full time

Benefits offered by this job

Medical, dental, and vision insurance

401(k)

Short-Term Disability (STD)

Life Insurance

AD&D Insurance

Company holidays

Birthday off

Paid Parental Leave

Flexible Paid Time Off (PTO)

Employee Assistance Program (EAP)

Monthly Stipend

Exposure to North America leadership

Job summary

Chowbus is seeking a Director of Sales Strategy in Chicago to shape and execute growth across markets, pricing, and commercial strategy. The role blends strategic planning with hands-on execution in a fast‑growing SaaS and restaurant tech environment, requiring travel and Mandarin-English fluency.

You will partner with senior leadership, translate goals into initiatives, and drive pricing, packaging, and GTM decisions while building a small strategy team as Chowbus expands.

Qualifications

• 8+ years of experience in Sales Strategy, Commercial Strategy, Business Strategy, Growth Strategy, Management Consulting, or a related strategic function.
• Proven experience developing strategies that drive revenue growth, product growth, market expansion, or sales effectiveness.
• Strong commercial mindset connecting product, pricing, market, sales, and revenue.
• Experience with pricing, product commercialization, or go-to-market strategy.
• Strong analytical and problem-solving skills to turn complex business problems into clear recommendations.
• Experience in SaaS, POS, payments, restaurant technology, marketplace, or other B2B technology businesses is highly preferred.
• Strong understanding of B2B sales and complex products or customer segments.
• Excellent cross-functional communication and stakeholder management skills, with the ability to influence without direct authority.
• Strong executive communication and presentation skills.
• Comfortable working in both strategic and hands-on environments.
• Willingness and ability to travel regularly for market visits, customer meetings, and business initiatives.
• Fluency in English and Mandarin Chinese is required.
• Ability to work from Chowbus Chicago office.

Responsibilities

• Develop and execute Chowbus’ Sales and Commercial Strategy in partnership with senior leadership.
• Translate company goals into strategic priorities, business plans, and actionable initiatives.
• Identify growth opportunities across markets, customer segments, products, and sales channels.
• Develop recommendations around where to play, what to sell, who to target, and how to win.
• Partner with Sales Leadership to translate strategy into clear sales priorities and execution plans.
• Analyze sales performance, market trends, and customer insights to identify growth opportunities.
• Lead strategic initiatives focused on product growth and commercialization.
• Evaluate market demand, customer needs, competitive positioning, and revenue potential across products.
• Partner with Product and Sales teams on product positioning, packaging, and go-to-market strategy.
• Lead analysis and recommendations around pricing, packaging, and product economics.
• Evaluate pricing competitiveness and alignment with customer value.
• Provide data-driven recommendations on product and pricing decisions.
• Conduct market research to identify industry trends, customer needs, competitive dynamics, and growth opportunities.
• Analyze competitors across restaurant technology, POS, payments, SaaS, and related markets.
• Research third-party products and solutions to assess customer value, market relevance, and commercial potential.
• Conduct customer and merchant research to validate strategic assumptions and identify opportunities.
• Translate market insights into actionable recommendations for Sales, Product, and leadership.
• Partner with Sales Leadership to ensure sales teams understand and execute strategic priorities.
• Develop strategic training, enablement materials, and business insights for Sales teams.
• Help define clear ownership and accountability across Strategy, Sales, Product, Operations, and other functions.
• Lead cross-functional strategic initiatives from analysis through execution.
• Serve as a strategic partner to senior leadership and provide clear, data-driven recommendations.
• As the organization grows, help build and manage a small strategy team.
• Spend approximately 20% of your time in the market engaging with merchants, customers, sales teams, and industry stakeholders.
• Conduct market visits and customer discovery to develop firsthand insights.
• Work directly with Sales teams to understand market challenges and validate strategic recommendations.
• Travel periodically for customer meetings, market research, sales initiatives, and other business priorities.

Job description

Chowbus is a leading AI Asian restaurant technology SaaS platform with deep roots in the North American market. We currently serve more than 10,000 Asian restaurants across 30+ states and 100+ key cities in the U.S. We build technology solutions across POS, AI, and digital tools that help restaurant operators improve efficiency, reduce operating costs, and grow their businesses. As Chowbus continues to expand its product portfolio, customer base, and sales organization, we are looking for a Director of Sales Strategy to help shape and execute the company’s next stage of growth. This is a highly strategic, cross‑functional role focused on sales strategy, product growth, pricing, market intelligence, and commercial execution. The ideal candidate combines strong strategic thinking with hands‑on execution and can turn complex business questions into clear priorities and actionable plans.

What You’ll Focus On

Sales Strategy & Growth

• Develop and execute Chowbus’ Sales and Commercial Strategy in partnership with senior leadership.
• Translate company goals into strategic priorities, business plans, and actionable initiatives.
• Identify growth opportunities across markets, customer segments, products, and sales channels.
• Develop recommendations around where to play, what to sell, who to target, and how to win.
• Partner with Sales Leadership to translate strategy into clear sales priorities and execution plans.
• Analyze sales performance, market trends, and customer insights to identify growth opportunities.

Product Growth & Pricing

• Lead strategic initiatives focused on product growth and commercialization.
• Evaluate market demand, customer needs, competitive positioning, and revenue potential across products.
• Partner with Product and Sales teams on product positioning, packaging, and go‑to‑market strategy.
• Lead analysis and recommendations around pricing, packaging, and product economics.
• Evaluate pricing competitiveness and alignment with customer value.
• Provide data‑driven recommendations on product and pricing decisions.

Market & Competitive Intelligence

• Conduct market research to identify industry trends, customer needs, competitive dynamics, and growth opportunities.
• Analyze competitors across restaurant technology, POS, payments, SaaS, and related markets.
• Research third‑party products and solutions to assess customer value, market relevance, and commercial potential.
• Conduct customer and merchant research to validate strategic assumptions and identify opportunities.
• Translate market insights into actionable recommendations for Sales, Product, and leadership.

Sales Enablement & Cross‑Functional Leadership

• Partner with Sales Leadership to ensure sales teams understand and execute strategic priorities.
• Develop strategic training, enablement materials, and business insights for Sales teams.
• Help define clear ownership and accountability across Strategy, Sales, Product, Operations, and other functions.
• Lead cross‑functional strategic initiatives from analysis through execution.
• Serve as a strategic partner to senior leadership and provide clear, data‑driven recommendations.
• As the organization grows, help build and manage a small strategy team.

Market Execution

• Spend approximately 20% of your time in the market engaging with merchants, customers, sales teams, and industry stakeholders.
• Conduct market visits and customer discovery to develop firsthand insights.
• Work directly with Sales teams to understand market challenges and validate strategic recommendations.
• Travel periodically for customer meetings, market research, sales initiatives, and other business priorities.

What You Bring

• 8+ years of experience in Sales Strategy, Commercial Strategy, Business Strategy, Growth Strategy, Management Consulting, or a related strategic function, preferably within a high‑growth technology or SaaS company.
• Proven experience developing strategies that drive revenue growth, product growth, market expansion, or sales effectiveness.
• Strong commercial mindset with the ability to connect product, pricing, market, sales, and revenue.
• Experience with pricing, product commercialization, or go‑to‑market strategy.
• Strong analytical and problem‑solving skills, with the ability to turn complex business problems into clear recommendations.
• Experience in SaaS, POS, payments, restaurant technology, marketplace, or other B2B technology businesses is highly preferred.
• Strong understanding of B2B sales and complex products or customer segments.
• Excellent cross‑functional communication and stakeholder management skills, with the ability to influence without direct authority.
• Strong executive communication and presentation skills.
• Comfortable working in both strategic and hands‑on environments.
• Willingness and ability to travel regularly for market visits, customer meetings, and business initiatives.
• Fluency in both English and Mandarin Chinese is required.
• Ability to work from the Chowbus Chicago office.

What We Offer

• Competitive compensation package
• Medical, dental, and vision insurance
• 401(k)
• 100% employer‑paid Short‑Term Disability (STD)
• 100% employer‑paid Life Insurance
• 100% employer‑paid AD&D Insurance
• Company holidays
• Birthday off
• Paid Parental Leave
• Flexible Paid Time Off (PTO)
• Employee Assistance Program (EAP)
• Monthly Stipend
• Direct exposure to North America leadership and the opportunity to shape Chowbus’ next stage of growth

The salary for this role is $130,000–$180,000 base plus bonus/equity, depending on experience.