GTM Operations, Planning

About the Company

Sierra is creating a platform to help businesses build better, more human customer experiences with AI. Founded by Bret Taylor and Clay Bavor, the company is guided by values of Trust, Customer Obsession, Craftsmanship, Intensity, and Family.

Responsibilities

• Own GTM planning processes end-to-end, including annual/quarterly planning, quota setting, and headcount planning
• Partner with GTM and Finance leadership to develop revenue forecasts and resource allocation plans
• Own sales compensation and incentive programs, including plan design and administration
• Deliver actionable GTM performance insights and recommendations to improve efficiency
• Serve as a strategic partner to GTM, Finance, and Operations leadership to drive cross-functional alignment

Requirements

• 5–8 years of experience in private equity, venture capital, investment banking, or consulting
• Business planning or strategic finance experience at a high-growth technology company
• Exceptional financial modeling and analytical skills
• Experience with annual planning, revenue forecasting, or sales compensation
• Strong executive communication and stakeholder management skills
• Highly structured, detail-oriented problem solver

Preferred Qualifications

• SQL proficiency
• Experience with BI tools such as Hex or Tableau
• Prior ownership of GTM planning processes
• Previous startup or 0 to 1 operational experience in AI or SaaS