Remote Director, AI-Driven Sales Strategy & Ops

Alma; United States; Remote; USD 180,000 - 250,000; Full time

Benefits offered by this job

Health benefits

401(k) match

Parental leave

Professional development

Wellbeing programs

Job summary

Spring Health in the United States is seeking a Director of Sales Strategy & Operations to own annual and long-range planning for the Sales organization, partner with Finance and leadership, and drive AI-enabled productivity gains across the GTM motion.

You will lead a team of analysts, design territory models, forecast cadence, and execute cross-functional initiatives that translate strategic targets into actionable plans with measurable impact.

Qualifications

• 10+ years of experience in Revenue Operations, Sales Strategy, Business Operations, Consulting, or a related function at a high-growth B2B SaaS or technology company.
• 5+ years of people management experience, with a track record of developing high-performing teams and evolving team capabilities in response to changing business needs.
• Deep expertise in GTM planning, including annual planning, quota design, territory modeling, headcount planning, and long-range strategic planning.
• Strong analytics fluency, including proficiency with Omni (or equivalent BI tools such as Looker, Tableau, or Sigma) for building dashboards, data models, and self-serve reporting infrastructure.
• Advanced SQL skills or experience working alongside analytics engineering teams to define and validate data models.
• 2 years of demonstrable experience designing and deploying automation, AI, and/or ML systems in a GTM context (prospecting, forecasting, coaching, data enrichment to workflow automation, analysis acceleration)
• Proven ability to lead cross-functional strategic initiatives with executive-level stakeholders and to distill complex data into clear, actionable recommendations.
• Experience as an operational partner to segment or business unit leaders, translating business performance data into strategic recommendations and enabling field execution.

Responsibilities

• Lead annual and long-range planning end-to-end for the Sales organization — from capacity modeling and quota design to territory architecture and headcount alignment — translating company growth targets into executable GTM plans.
• Drive rigorous forecast cadence and scenario planning, partnering with Finance, Revenue Leadership and cross-functional teams to deliver predictable revenue outcomes and clear business visibility to the executive team.
• Architect and own a portfolio of strategic projects and cross-functional initiatives, acting as a trusted operator and thought partner to the SVP of Sales and business segments that are in support of our sales go-to-market motion (e.g., BDR)
• Own and execute the operating cadence and rhythm for the Sales organization across forecasting, pipeline, strategic deal reviews, and more.
• Lead and develop a team of analysts embedded within the Sales segment — evolving their role from operational executors to AI-enabled strategic builders who develop dashboards / AI agents in the field, while also being strong strategic and operational partners to leaders supporting with business reviews, pipeline hygiene, performance insights.
• Serve as the AI orchestration layer for and in support of the Sales team — defining how AI is adopted within the business segment and how the team deploys AI agents, automation, and analytics tools (including Claude) across people, process, and data to compound team productivity and decision-making velocity.
• Champion a culture of continuous experimentation and tooling adoption, identifying where AI can eliminate repetitive work, surface insights faster, and enable the team to operate at a level beyond headcount - this means daily experimentation

Skills

Revenue Operations

Sales Strategy

Business Operations

People Management

GTM Planning

Data Analytics

SQL

AI/Automation in GTM

Cross-functional Leadership

Executive Stakeholder Engagement

Tools

Looker

Tableau

Sigma

Omni

Claude API

Salesforce SFDC

Job description

Spring Health in the United States is seeking a Director of Sales Strategy & Operations to own annual and long-range planning for the Sales organization, partner with Finance and leadership, and drive AI-enabled productivity gains across the GTM motion.

You will lead a team of analysts, design territory models, forecast cadence, and execute cross-functional initiatives that translate strategic targets into actionable plans with measurable impact.