Head of Sales

Remote Full TimeUnited States (Remote)Origin Financials

About Origin

Origin is reimagining wealth management by making it accessible and affordable to all. Today, money is the [#1] source of stress – more than jobs, health, and relationships combined. That stress is exacerbated in the current economic environment, which is presenting people with once-in-a-generation financial challenges. Origin is tackling this problem head on by expanding access to financial planning for those who have historically been boxed out due to high barriers to entry. Our product simplifies finances for individuals making it easy to manage spend and investments, get expert advice, and take action to hit financial goals.

We are a fast-paced startup in the series B round, led by repeat founders and backed by leading VC firms like Founders Fund, Felicis, and General Catalyst.

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.


  • 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.



  • 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

About Originals

Fulfilling our mission is only possible with a diverse team that breathes for excellence and is hugely committed to making money simple for everyone, everywhere.

As a team, we are obsessed with delivering the best solution possible to our members through an elegant and self-guided experience. We know that building a product of this magnitude requires from us tons of creativity, autonomy, and flexibility to move fast and embrace uncertainties with ownership. This is who we daily pursue to be!

To embrace talented people like this and provide the necessary resources to achieve their best versions, we believe in the power of a healthy environment where each person is valued for who they are and have clear goals and expectations for the future they can build within the company. Each person here is seen as a key player in our team.

Our environment is diverse, with excellent people and equal opportunities. We believe in the power of the individuality and uniqueness of each of us to make our team even more powerful.

We are building an outstanding solution, and here is an invitation for you to become an Original and join us on this journey!

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