Business Systems Analyst, Revenue Operations at Headway | Powderkeg

Headway is building a new mental healthcare system that everyone can access. We make it easy for people to find quality in-network mental health care by removing historic barriers faced by mental health providers, payers, and patients.

1 in 4 people in the US have a treatable mental health condition, but the vast majority do not get the care they need. The primary reason is cost: the majority of therapists do not accept insurance, meaning paying for therapy is prohibitively expensive. This is where we got our start – Headway has built the first software-enabled national network of therapists who accept health insurance, making it possible for patients to find quality care they can afford and enabling mental healthcare providers to grow their practice.

We launched in April of 2019 and are now powering 500,000+ appointments a month. To scale our vision, we’ve raised over over $100 million in funding from a16z, Thrive, Accel, Spark Capital, and Google Ventures.

Join us, and make an impact

About The Role

Revenue Operations at Headway is a dynamic, data-driven team focused on optimizing the growth process, enhancing efficiency, and ultimately driving success in our mission to rebuild America's mental health system. We operate within three primary pillars: systems & processes, reporting & insights, and strategy. Our mandate includes supporting the Growth team, encompassing Provider Marketing, Sales, and Revenue & Retention, to scale and enhance our mental health therapist network. We leverage technology and data to provide the best solutions to our partner teams, from optimizing sales territories and formulating compensation plans, to implementing sales tools and analyzing performance metrics. Moreover, we ensure that our partners feel supported through actions such as quota setting, pipeline generation, payout calculation, and insightful reporting. In essence, our role is to streamline the sales process, enabling our teams to work more efficiently and effectively towards our shared goals.

As a Revenue Operations Lead (Business Systems Analyst) at Headway, you will play a pivotal role in our mission to reinvent the way people access mental health care. Your expertise will directly contribute to the transformation of our Salesforce ecosystem, ensuring that our therapists and users have an efficient and seamless experience. You will be responsible for documenting all requirements in Jira, providing detailed information on feature changes, and ensuring that the team is on track with deliveries. You will also quarterback our Salesforce Case system, ensuring that user requests are efficiently managed and resolved by the right team members. This role is critical in streamlining how Rev Ops and Salesforce Product take requests and deliver on those requests.

Key Responsibilities Include:

  • Develop, optimize, and efficiently deliver Salesforce configurations while adhering to best practices to support business processes and requirements.
  • Collaborate with cross-functional teams to gather and translate requirements into effective Salesforce solutions.
  • Manage and resolve user requests efficiently through our Salesforce Case system, implementing proactive measures to reduce recurring cases and enhance user experience.
  • Lead the restructuring of our Salesforce data model, catering to diverse user groups and sales motions.
  • Drive user adoption by designing intuitive features, providing comprehensive training and documentation, and ensuring proper education on new features and processes.
  • Measure the efficacy of all Salesforce implementations to drive continuous improvement.


  • 3-5 years' experience as a Business Systems Analyst, preferably within a SaaS environment.
  • 3+ years of hands-on experience with Salesforce, particularly in system design and optimization.
  • Certification in Salesforce is highly desirable.
  • Proven ability to dissect complex business processes and craft data-driven solutions.
  • Experience with project management (preferably Jira certification) and Agile methodologies.
  • Excellent collaboration and communication skills with a track record of working with cross-functional teams.
  • Experience in HealthTech or similar industries is a plus.
  • Resilient and comfortable in a fast-paced environment, with the ability to juggle multiple projects.
  • Bachelor's degree in a relevant field or equivalent experience.

You’d be a great fit if…

  • You have a Headway-first mentality and a lot of empathy for our users.
  • You have strong problem-solving skills and a keen eye for detail.
  • You have previous experience in a business systems analyst role, with exposure to Salesforce and Jira.
  • You have experience working with Lucid Charts or similar tools for process documentation and visualization.
  • You have the ability to manage multiple projects and priorities in a fast-paced, high-growth environment.
  • You are a strong communicator, with the ability to clearly and concisely explain complex processes and systems.
  • You have a passion for clean data and work tirelessly to ensure rules are in place to prevent data inconsistencies.

As a Revenue Operations Lead (BSA), your work will have a direct impact on Headway's efficiency and success. You will be instrumental in improving our systems and processes, enabling us to scale our operations and achieve our mission. This is a role with significant growth potential, offering the opportunity to make a real difference in a fast-growing company.

Compensation and Benefits:

  • Salary information is based on a single salary target per role and is differentiated based on geographic location (Group A, B, or C)

    • Group A: $125,000
    • Group B: $112,500
    • Group C: $100,000
    • Examples of cities located in each Compensation Grouping:
      • Group A = NYC/Tri-State Area, SF/Bay Area, LA Area, Seattle, Boston, Austin, and San Diego
      • Group B = Chicago, Miami, Denver, Washington DC, Philadelphia, Atlanta, Minneapolis, Nashville, Sacramento, Phoenix, and Portland
      • Group C = All remaining cities
    • Other compensation includes: discretionary bonuses
  • Benefits offered include:

    • Medical, Dental, and Vision coverage
    • HSA / FSA
    • 401K
    • Work-from-Home Stipend
    • Therapy Reimbursement
    • 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
    • Unlimited PTO
    • Employee Assistance Program (EAP)
    • Training and professional development

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem - across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience.

Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please contact

Headway employees work remotely across the US, with the option to work from offices in New York City and (coming soon!) San Francisco. Headway participates in E-Verify. To learn more, click here.

Job Summary
  • Job Title
    Business Systems Analyst, Revenue Operations
  • Company
  • Location
  • Employment Type
    Full time
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