Client Executive, Mid-Market

Headspace

18h•$75,000 - $100,000•Hybrid

About The Position

Headspace's Client Success team engages our clients to drive adoption, engagement, and demonstrate ongoing value. This critical function is responsible for onboarding new clients, driving ongoing adoption and engagement strategies, and managing renewals and expansions. Our Client Success Group works cross-functionally with the rest of the Headspace organization to uncover new ways to make Headspace a part of everyday life and to improve our product. In this role, you'll help build lasting relationships with a growing portfolio of clients and play a meaningful role in helping people access mental health support through their employers.

Requirements

4+ years of experience in Customer Success, Account Management, Relationship Management, or a similar client-facing role
Proven ability to manage and grow client relationships with a focus on retention and engagement
Strong communication skills — organized, clear, and able to tailor messaging to different audiences
Empathetic and solutions-oriented mindset with a genuine desire to help clients succeed
Comfortable working in a fast-paced, high-growth environment with shifting priorities
Results-driven with strong attention to detail and follow-through
Experience delivering metric-based reporting and translating data into actionable insights
Familiarity with Salesforce or similar CRM tools

Nice To Haves

Experience in benefits, wellness, healthcare, or a related industry
Background supporting SMB or Mid-Market clients specifically
Experience with upsell and expansion conversations within an existing book of business

Responsibilities

Managing a portfolio of SMB and Mid-Market clients, serving as their point of contact and trusted advisor throughout the client lifecycle
Build and maintain strong client relationships by communicating Headspace's value, responding to inquiries, and troubleshooting issues in a timely and professional manner
Monitor client health and risk, proactively identifying opportunities to deepen relationships and drive engagement across client organizations
Partner with clients to support onboarding, adoption strategies, and renewals, ensuring they are getting measurable value from Headspace
Support clients through contract renewals and expansions, helping guide them through pricing and partnership decisions
Provide regular reporting to clients that demonstrates the impact and value Headspace delivers for their employees
Maintain accurate and up-to-date client documentation across internal systems, including Salesforce, Asana, Google Suite, Highspot, Brandfolder, Ironclad, and AI tools such as - ChatGPT, Claude, and/or Gemini
Collaborate with internal teams — including Sales, Product, and Marketing — to share client insights, represent the voice of the customer, and improve our overall offering
Work with third-party partners on behalf of clients, including consultants and eligibility vendors, as needed