Chief of Staff, Head of Product Strategy & GTM

📋 Description

• Support end-to-end product strategy, monetization, and GTM for Auto Integrate products.
• Partner with Sales, Product, Engineering, Finance, and Ops to define 3-year vision and pricing.
• Define pricing, packaging, and monetization to balance value with revenue growth.
• Lead GTM motions to drive new logos, product activation, and expansion.
• Prepare executive materials and dashboards to monitor performance and pricing impact.
• Must be located in Eastern Standard Time.

🎯 Requirements

• 7-10+ years in network B2B SaaS and/or payments across product, strategy, or pricing.
• Proven track record owning product strategy and roadmaps for material product lines.
• Deep pricing expertise, including usage-based models and multi-product monetization.
• Strong product marketing and GTM experience; capable of scalable product launches.
• Analytical and financial acumen; able to model P&L impact.
• 2+ years at a top-tier consulting firm advising on product strategy and pricing (preferred).
• Experience in fleet, logistics, mobility, or related verticals is a plus.

🎁 Benefits

• Multiple health/dental coverage options (100% employee, 50% for family)
• Vision insurance
• Incentive stock options
• 401(k) match of 4%
• PTO - 4 weeks (increases at year two!)
• 12 company holidays + 2 floating holidays