Director of Sales Strategy and Operations

Role Overview

This leader will act as a force multiplier for Sales and Account Management by ensuring teams are focused on the right opportunities, executing with discipline, and making sound commercial decisions. The role will partner closely with Sales Leadership, Account Management, Finance, Marketing, Service Delivery, Legal, and Deal Desk to improve pipeline quality, forecast accuracy, cross sell / upsell execution, pricing discipline, and overall revenue performance.

What You Will Do

Key responsibilities include sales enablement and performance support, new logo performance optimization, cross sell, upsell, and account growth strategy, deal desk participation and commercial governance, compensation plan design and management, forecasting, pipeline, and performance management, pricing strategy & optimization, process and operational excellence, and cross-functional leadership.

Why It Might Be a Fit

The successful candidate will operate as a strategic revenue operator, not just a reporting function, and bring discipline to pipeline quality, forecasting, cross sell / upsell execution, and Deal Desk decisions.

Requirements

• 8–12+ years of experience in Sales Leadership, Sales Operations, Sales Strategy, Deal Desk, or Sales Leadership support roles
• Experience supporting both new logo / hunter sales teams and account management / expansion teams
• Strong background in B2B services, MSP, SaaS, technology services, or recurring revenue environments
• Deep expertise in pipeline management, forecasting, compensation design, sales process, account planning, and commercial deal review
• Experience participating in Deal Desk processes, including pricing, margin review, discounting, contract terms, and exception approval workflows
• Proven ability to influence and challenge senior sales leaders constructively
• Strong analytical, financial modeling, and business judgment skills
• Experience with CRM and PSA tools such as HubSpot, ConnectWise PSA, or similar platforms
• Excellent communication skills and executive presence
• Experience with channel / partner sales programs preferred

Benefits

• Medical
• Dental
• Vision
• Disability
• Group term life insurance
• 401K
• PTO
• Holiday pay
• Referral bonuses

Tagged as: Compensation Design, Deal Desk, Financial Modeling, Forecasting, HubSpot