Head of 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