Headspace

Client Executive, Mid-Market

Headspace$75K — $100K *
US-AnywhereRemote in United States
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 4+ years of experience in Customer Success or Account Management
  • Proven ability to manage and grow client relationships
  • Strong communication skills tailored to different audiences
  • Empathetic and solutions-oriented mindset
  • Able to thrive in a fast-paced, high-growth environment
  • Results-driven with attention to detail
  • Experience with metric-based reporting and CRM tools like Salesforce

Responsibilities

  • Manage a portfolio of SMB and Mid-Market clients as their trusted advisor
  • Build and maintain strong client relationships
  • Monitor client health and proactively identify deepening relationship opportunities
  • Support clients during onboarding, adoption, and renewals
  • Provide regular reporting demonstrating impact and value to clients
  • Maintain accurate client documentation across various internal systems
  • Collaborate with internal teams to share client insights and improve offerings
  • Work with third-party partners on behalf of clients

Benefits

  • Comprehensive healthcare coverage
  • Monthly wellness stipend
  • Retirement savings match
  • Lifetime Headspace membership
  • Generous parental leave
  • Opportunity for variable compensation and equity
Full Job Description
What you will do:
  • This role's primary focus is 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

What you will bring:

Required Skills:
  • 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

Preferred Skills:
  • 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

Location:

We are currently hiring this role remotely in the US and Hybrid for San Francisco, CA. Candidates must permanently reside in the US full-time.

For candidates with a primary residence in the greater SF area, this role will follow our hybrid model. You'll work 3 days per week from our office, allowing for impactful in-office collaboration and connection, while enjoying the flexibility of remote work for the rest of the week. Your recruiter will share more details about our hybrid model.

Pay & Benefits:

The anticipated new hire base salary range for this full-time position is $75,000-$100,000 + variable compensation + equity + benefits.

Our salary ranges are based on the job, level, and location, and reflect the lowest to highest geographic markets where we are hiring for this role within the United States. Within this range, individual compensation is determined by a candidate's location as well as a range of factors including but not limited to: unique relevant experience, job-related skills, and education or training.

Your recruiter will provide more details on the specific salary range for your location during the hiring process.

At Headspace, base salary is but one component of our Total Rewards package. We're proud of our robust package inclusive of: base salary, stock awards, comprehensive healthcare coverage, monthly wellness stipend, retirement savings match, lifetime Headspace membership, generous parental leave, and more. Additional details about our Total Rewards package will be provided during the recruitment process.

#LI-REMOTE

About Headspace

Headspace is a digital health platform that provides guided meditation sessions and mindfulness training. The company was founded in 2010 by Andy Puddicombe and Rich Pierson, and has since grown to become one of the most popular meditation apps in the world, with over 65 million users in more than 190 countries. Headspace offers a variety of meditation programs, including stress reduction, sleep improvement, and focus enhancement, and has partnerships with major companies such as Google, Nike, and Apple. The company is committed to making meditation accessible to everyone, and offers a free version of its app as well as a paid subscription service.
Learn more about Headspace
Size
500 employees
Industry
Founded
2010

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