Director, Sales Strategy

Leadout Capital; San Francisco (CA); On-site; USD 180,000 - 260,000; Full time

Job summary

Leadout Capital is seeking a seasoned Sales Strategy leader to join our Regulated Industries team. You will bridge strategy and execution across Sales, Finance, Marketing and Operations, shaping GTM plans and territory design.

You will influence EVP-level and C-suite executives, build analytics dashboards, and drive multi-functional initiatives in a fast-growth SaaS environment. Strong leadership and communication are essential for success.

Qualifications

• 10+ years in management consulting, sales strategy, or business operations within a SaaS or high-growth environment.
• 2nd line People Manager experience.
• Ability to advise and influence EVP-level and C-suite executives.
• Deep understanding of enterprise software sales models, product-led growth, and consumption-based business models.
• Strong quantitative analysis and financial modeling skills with Excel or Google Sheets.
• Track record of developing and executing GTM strategies within complex, matrixed organizations.
• Excellent storytelling skills for executive stakeholders.
• Experience driving large-scale business transformation and organizational change initiatives.

Responsibilities

• GTM Strategy & Planning: translate vision into executable GTM plans with account segmentation, resource allocation, quota setting, and territory design.
• Rhythm of Business: drive forecast management to ensure predictable growth and oversee weekly forecast calls.
• Business Analytics: build dashboards/reports tracking KPIs and run ad-hoc analyses of business health.
• Cross-Functional Execution: drive long-term transformational initiatives across the organization.

Skills

Management consulting

Sales strategy

Business operations

Executive communication

Analytical rigor

GTM strategy

Forecasting

Leadership

Education

MBA

Tools

Excel

Google Sheets

Salesforce

Tableau/CRM Analytics

Job description

The Sales Strategy team for Regulated Industries is a high-performance group of trusted advisors embedded with senior leaders to drive strategic clarity and sustainable growth. In this role, you will sit at the intersection of strategy and execution, connecting dots across Sales, Finance, Marketing, and Operations. You are equally comfortable presenting in the boardroom as you are unblocking processes or re-engineering a territory model.

Responsibilities

• GTM Strategy & Planning: Act as a trusted co-pilot to the Regulated Industries VP of Strategy and the COO, translating vision into executable GTM plans, including account segmentation, resource allocation, quota setting, and territory design.
• Rhythm of Business: Drive forecast management excellence to ensure sustained, predictable growth; coordinate weekly forecast calls and rigorously inspect pipeline health.
• Business Analytics: Provide the analytical bedrock for leadership decisions by building dashboards and reports that track key performance metrics and running ad-hoc analyses to diagnose business health.
• Cross-Functional Execution: Navigate organizational complexity to drive execution of long-term transformational initiatives.

Required Qualifications

• Proven Experience: 10+ years in management consulting, sales strategy, or business operations within a SaaS or high-growth environment.
• Leadership: Proven experience as a 2nd line People Manager.
• Executive Influence: Demonstrated ability to advise and influence EVP-level and C-suite executives.
  Domain Knowledge: Deep understanding of enterprise software sales models, product-led growth, and consumption-based business models.
• Analytical Rigor: Strong quantitative analysis and financial modeling skills, with advanced proficiency in Excel or Google Sheets.
• Strategic Execution: A track record of developing and executing GTM strategies within complex, matrixed organizations.
• Communication: Excellent storytelling skills, able to distill complex information into clear narratives for executive stakeholders.
• Change Management: Experience driving large-scale business transformation and organizational change initiatives.

Preferred Qualifications

• Platform Expertise: Salesforce (CRM) experience and proficiency with data visualization tools like Tableau or CRM Analytics.
• Market Expertise: Experience in Regulated Industries and an understanding of its specific business dynamics.
• Technical Skills: Experience with SQL (or equivalent database querying language) and Claude is a plus.
• Growth Strategies: Specific experience with consumption-based pricing models and usage-driven growth.
• Education: An MBA or equivalent advanced degree.
• Program Excellence: A track record of successful program execution in high-growth technology environments.