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Head of Sales

Remote | US
Sales

What's this role mission

To double B2B ARR by the end of 2025 by crafting and executing a strategic sales plan that leverages in-depth data analysis and fosters strong cross-functional partnerships. This role focuses on generating comprehensive growth strategies, expanding market reach, and enhancing sales operations for greater efficiency and scale.

What You'll Do:

  • Develop and implement a sales strategy to drive growth and market expansion.
  • Work closely with partners to execute our voluntary benefits playbook, potentially including its development, to leverage the B2B2C partnerships channel, a significant revenue source.
  • Build and lead a high-performing sales team to exceed sales targets.
  • Optimize sales operations for efficiency and scalability.
  • Identify and penetrate new markets or segments to increase revenue.
  • Enhance customer acquisition and retention strategies.
  • Facilitate cross-functional collaboration to ensure cohesive go-to-market strategies.
  • Increase sales efficiency from Sales Development Representatives.
  • Train AEs and SDRs to perform outbound sales activities.
  • Deliver monthly forecast reports with 100% accuracy.
  • Design and roll out sales training to all client-facing employees.

Our ideal fit:

  • Can develop and execute clear, actionable strategies that drive revenue growth and market expansion.
  • Excel in sales operations, including forecasting, pipeline management, and CRM use.
  • Can make decisions based on data analysis, market trends, and sales metrics.
  • Can engage and influence across all organizational levels and with customers. Initiates actions and strategies independently, demonstrating initiative.
  • Seeks out new knowledge and insights to improve strategies and processes.
  • Pursues sales targets and goals with determination.
  • Ensures all promises and objectives are met.
  • Maintains a high level of accuracy in all sales and operational activities.
  • Anticipates needs and challenges, acting ahead of potential issues.
  • Can mentor and grow team members to enhance their skills and performance.
  • Demonstrates dedication and commitment to achieving business goals.
  • Maintains composure and decision-making quality in high-stress situations.
  • Can adjust strategies and approaches in response to changing market conditions and business needs.

Qualifications:

  • Bachelor's degree in Business, Marketing, Finance, or a related field.
  • Minimum of 10 years of Sales experience in the B2B SaaS space, with at least 5 years in a leadership role.
  • Proven track record of achieving and exceeding sales targets, ideally within fintech or benefits solutions selling into HR/CHRO.
  • Exceptional negotiation, strategic planning, and relationship management skills.
  • Strong analytical skills, with the ability to translate complex data into actionable strategies.
  • Exceptional leadership qualities, capable of motivating and guiding a sales team towards achieving ambitious goals.
  • Excellent communication and interpersonal skills, with a knack for building relationships with a diverse range of stakeholders.
  • Deep understanding of sales processes and dynamics. A focus on fintech and benefits markets a plus.
  • Agile and adaptable, with a proven ability to thrive in a fast-paced and evolving business environment.
  • Proven ability to work cross-functionally, leading and influencing teams without formal authority.

WHAT WE OFFER

Compensation

  • Generous base salary
  • Meaningful equity package

Health and Wellness

  • Health Insurance
  • Life insurance
  • 401K
  • Wellness allowance
  • Mental health care
  • Parenthood & fertility
  • Unlimited access to Origin
  • Co-working allowance
  • Work setup one-time stipend

Work-life rhythm

  • Unlimited PTO
  • Parental leave
  • Remote-first
  • Flexible hours

 

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