Director, Sales Strategy & Operations - Groups

Accountabilities: Sales Strategy and Segmentation: Own the sales segmentation strategy, including ideal customer profiles, account scoring methodologies, territory design, and coverage models. Identify opportunities to improve market penetration, resource allocation, and sales effectiveness. Strategic Planning and Capacity Modeling: Partner with GTM Finance to develop capacity models, establish sales targets, support annual planning, and build multi-year headcount plans aligned with business objectives. Performance Measurement and Business Intelligence: Define key performance indicators, data instrumentation, and analytical frameworks that provide leadership with actionable insights into sales performance, pipeline health, and growth opportunities. Sales Operating Cadence: Establish and manage the sales organization's operating rhythm, including annual planning, forecasting, pipeline reviews, quarterly business reviews, and executive performance reporting. Sales Process Optimization: Design, implement, and maintain a consistent end-to-end sales process, establishing standards for selling, forecasting, reporting, and pipeline management. Identify operational bottlenecks and implement improvements that increase productivity and execution quality. AI Strategy and Implementation: Define and execute the strategy for integrating AI into the sales lifecycle, including prospecting, forecasting, deal execution, and coaching. Establish measurable productivity goals and ensure AI initiatives deliver tangible business outcomes. Systems and Technology Collaboration: Work closely with GTM Systems to develop, implement, and drive adoption of the tools, automation, AI capabilities, and insights that support sales execution. Data-Driven Experimentation: Develop and test hypotheses related to segmentation, sales coverage, resource allocation, and productivity. Translate analytical findings into strategic recommendations and operational decisions. Cross-Functional Partnership: Collaborate with Revenue Enablement, Growth, Central Data, GTM Finance, and Corporate Finance to align sales strategy, tools, training, and financial planning with organizational priorities. Team Leadership and Development: Recruit, manage, and develop a team of two to four analysts and strategy partners over the first 12 to 18 months, establishing clear priorities, analytical standards, and a culture of accountability. Executive Advisory: Serve as a trusted strategic and operational partner to senior sales leadership, providing data-backed recommendations, challenging assumptions, and helping resolve competing priorities. Requirements Professional Experience: At least 8 years of experience in sales strategy and operations, revenue operations, or top-tier management consulting, including substantial experience in a high-growth B2B SaaS, fintech, or marketplace business. Strategic Leadership: Demonstrated experience serving as the primary strategic and operational partner to a VP-level or C-suite revenue leader, with a track record of translating business strategy into measurable results. AI and Automation Expertise: A clear perspective on how AI and automation can improve modern sales organizations, supported by practical experience implementing and scaling AI-driven solutions that deliver measurable productivity improvements. Sales Operations Expertise: Deep knowledge of sales mechanics, including pipeline analytics, capacity planning, territory design, forecasting methodologies, sales compensation planning, and go-to-market strategy. Analytical and Modeling Skills: Strong quantitative and problem-solving abilities, with the confidence to build and validate financial models, performance analyses, and operational frameworks independently before delegating or scaling them. Data-Driven Decision-Making: Experience defining performance metrics, analyzing business trends, testing hypotheses, and translating complex data into clear recommendations for senior leadership. Process Design and Optimization: Proven ability to establish scalable sales processes, improve operational workflows, identify productivity bottlenecks, and drive consistent execution across a sales organization. Cross-Functional Collaboration: Ability to work effectively with Finance, Data, Growth, Systems, and Enablement teams to align resources, technology, and operational priorities. Executive Communication and Influence: Excellent communication and stakeholder management skills, with the ability to influence senior leaders without direct authority, navigate competing priorities, and build alignment around data-backed decisions. People Management: The ability to recruit, lead, and develop analytical and strategic talent, establish clear performance expectations, and foster a culture of ownership and continuous improvement. Strategic and Hands-On Mindset: A combination of high-level strategic thinking and practical execution, with a willingness to investigate problems directly, build analytical solutions, and remain accountable for business outcomes. Benefits Competitive base salary: Annual compensation ranging from $170,000 to $230,000, depending on experience, expertise, and location. Equity compensation: Equity opportunities for all employees, allowing team members to participate in long-term business growth. Performance-based incentives: Additional annual bonuses may be available depending on the role and compensation structure. Flexible work arrangements: Remote opportunities within the United States, supported by a hybrid-hub model for employees who benefit from working in an office. Collaborative work environment: Access to the resources and tools needed to succeed in a flexible working environment. Leadership opportunities: The chance to build and lead a team of analysts and strategy partners while shaping the future of sales strategy and operations. Professional growth: Opportunities to develop expertise in AI-driven sales operations, revenue strategy, business analytics, and scalable go-to-market systems. High-impact ownership: Direct influence on sales productivity, operational efficiency, strategic planning, and revenue growth within an expanding business.