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Head of Customer Success



Customer Service, Sales & Business Development
United States · New York, USA · Boston, MA, USA · Remote
Posted on Friday, May 10, 2024


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.


Origin is seeking a driven Head of Customer Success to lead our customer success initiatives, ensuring optimal client engagement and satisfaction with our financial wellness solutions. This pivotal role involves developing strategies to maximize customer retention and success, growing Net Retention Revenue while managing a dedicated team to execute these plans effectively. This position is crucial for guiding the company through a significant growth phase, with the goal of substantially increasing annual recurring revenue.

What You'll Do:

  • Develop and implement customer success strategies to enhance customer satisfaction and retention.
  • Collaborate with the product and marketing teams to align customer success initiatives with broader company strategies.
  • Develop strategies to monetize customer success efforts, identifying upselling and cross-selling services and tiers within the existing customer base.
  • Manage customer success team, setting objectives and performance metrics aligned with business goals.
  • Grow and lead a high-performing customer success team to exceed renewal and upsell targets.
  • Work closely with the sales team to ensure a seamless transition from sales to post-sales, aligning on goals and strategies that facilitate ongoing customer engagement and revenue opportunities.
  • Lead onboarding and ongoing support programs for clients, ensuring smooth transitions and continued engagement.
  • Increase the lifetime value of customers through strategic account management, ensuring that customers receive tailored services that meet their evolving needs.
  • Oversee the delivery of services, ensuring they are executed efficiently and align with customer goals. Streamline processes to reduce costs and improve customer satisfaction.
  • Optimize Customer Success operations for efficiency and scalability.
  • Handle key customer relationships, providing strategic insights and solutions to their challenges.
  • Prepare and present detailed reports on team performance, customer health scores, and retention rates.
  • Deliver monthly forecast reports with 100% accuracy.

Our ideal fit:

  • A proven track record in developing and executing clear, actionable strategies that drive revenue growth and market expansion.
  • Excel in customer success operations, including forecasting, metric tracking and reporting, and
  • Can make informed 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 renewals and upsell targets and goals with determination.
  • Maintains and holds the team to a high level of accuracy in all customer success and operational activities.
  • Anticipates needs and challenges, proactively managing potential issues.
  • Passionate about mentoring and growing 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
  • Minimum of 10 years of Customer Success experience in the B2B SaaS or Benefits space, with at least 5 years in a leadership role.
  • Proven track record of maintaining and growing customer satisfaction and retention, working with HR/Benefits leaders a plus
  • 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 CS team towards achieving ambitious goals.
  • Excellent communication and interpersonal skills, adept at building relationships with a diverse range of stakeholders.
  • Strong analytical skills, with the ability to translate complex data into actionable customer engagement strategies.
  • Agile and adaptable, thriving in a fast-paced and evolving business environment.



  • 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;


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!