Director of Sales Strategy and Operations (Sales Planning and Analysis)

About the Team:

The Sales Operations team provides the analytical, technical, and process underpinning of a 1000-person+ go-to-market team.  From providing reporting and analysis, to developing new processes, to using technology to improve our teams, we wake up each day trying to improve sales performance.   You can be a part of this critical function!

Position Overview: We are seeking an experienced and dynamic Director of Sales Strategy & Operations, to lead and optimize our sales organization through data-driven strategies and operational excellence. This individual will focus on sales performance optimization, headcount planning, profitability analysis, and sales coordination and strategic planning across multiple teams/channels. They will work closely with cross-functional partners to ensure seamless operations and alignment with business objectives. This role requires a hands-on leader who is action-oriented, has a strong analytical mindset, and can influence without authority. You will need to balance both strategy and with day-to-day execution and play a key role in shaping the future of our sales organization.

Key Responsibilities:

• Sales Performance Optimization & Reporting:
  • Conduct in-depth sales trend analysis to provide actionable insights and drive continuous improvements in sales strategies.
  • Lead dial profitability analysis to optimize sales outreach effectiveness and efficiency.

• Offer Strategy & Channel Coordination:
  • Collaborate with cross-functional teams (Finance, HR, Marketing) to develop and optimize sales offer strategies that drive growth and profitability.
  • Oversee sales coordination efforts across email marketing, SEO/SEM, app, and online enrollment channels to ensure seamless customer journeys.
• Sales Planning:
  • Lead the annual and quarterly sales planning process, including forecasting, territory management, and resource allocation.
  • Lead the planning and execution of key sales events, aligning sales goals with organizational priorities.
• Headcount Planning & Optimization:
  • Drive headcount strategy, including hiring class sizes, location planning, and headcount forecasts to ensure we meet targets.
  • Work with HR to manage recruitment timelines and monitor the productivity of new hires to achieve optimal sales performance.

What You’ll Bring:

• Leadership & Influence: Ability to lead through influence and work cross-functionally to build consensus, push back where required and drive initiatives forward in a thoughtful way.
• Action-Oriented: A hands-on, self-sufficient leader who can execute independently and take full ownership of key responsibilities driving initiatives to completion
• Hands-on style: This leader will be expected to roll up their sleeves and dive deep into problem-solving and execution.
• Analytical Mindset: Strong analytical skills with a proven ability to use data to inform decisions and optimize sales operations.
• Strategic Thinker: Demonstrated success in strategic planning and operational execution in a high-growth sales environment.
• Strong Communication: Excellent verbal and written communication skills, with the ability to present data and insights to leadership and stakeholders.

Who you are:

• Bachelor’s degree in Business, Analytics, Finance, or related field; MBA or advanced degree preferred.
• 8+ years of experience in Sales Operations, Strategy, Analytics, or related roles, with at least 3 years in a leadership role.
• Experience in sales strategy and operations, sales planning, sales optimization
• Proven track record of success in working with cross-functional teams and leading initiatives in a fast-paced, data-driven environment.
• Intellectual curiosity balanced with an orientation for getting stuff done.
• Strong analytical and problem-solving skills with the ability to develop actionable insights and recommendations.
• Excellent communication skills with the ability to collaborate and influence cross-functional teams.
• Proficiency in sales tools and analytics platforms (e.g., Salesforce, Tableau, Power BI, SQL etc.).

We value diversity

We know that the best ideas come from teams where diverse points of view uncover new solutions to hard problems. We welcome and value individuals who bring diverse life experiences, educational backgrounds, cultures, and work experiences.

Compensation & Benefits:

• The salary band for this position ranges from $160,000 - $215,000, commensurate with experience and performance. Compensation may vary based on factors such as cost of living.
• This position will be eligible for a competitive year end performance bonus & equity package
• Full medical, dental, vision package to fit your needs
• Flexible vacation policy; work hard and take time when you need it
• Pet discount plans & retirement plan with company match (401K)
• The rare opportunity to work with sharp, motivated teammates solving some of the most unique challenges and changing the world

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