Head of Customer Success & Operations

About the role

This is a founding, high-impact leadership position for the Innovation team. The role is deeply hands-on and customer-facing, especially at the start, while also creating the structures, playbooks, and systems needed for a scalable customer success operation. It is suited to someone who has previously built a CS function from the ground up and is excited to do it again in a more early-stage, higher-stakes environment.

Core scope

• Take direct ownership of onboarding and supporting the first Alpha providers, personally handling inbound questions during the initial 6–8 weeks to build product understanding and customer insight.
• Capture and transcribe provider conversations to create a structured question framework that becomes the backbone of the AI support knowledge base.
• Maintain and improve the AI customer success agent corpus by organizing weekly engineer inputs, refining the knowledge base, publishing updates, and checking outputs for accuracy and PHI safety.
• Develop and document the PHI routing framework before launch, including clear rules for AI handling, human escalation, and urgent clinical escalation.
• Bring on a licensed clinical consultant such as an LCSW, LPC, or LMFT on retainer within 30–60 days after launch to handle high-risk clinical accuracy escalations.
• Create the Nitro CS runbook, CE handoff documentation, trust-repair messaging, and provider communications playbook in real time as the work evolves.
• Set the long-term customer success direction, including team design, hiring and onboarding plans, operating metrics, and tooling decisions.
• Share best practices with the Customer Success Learning and Enablement team so AI knowledge management standards and protocols stay aligned.
• Evaluate the AI CS agent platform around Week 4 and oversee rollout during Weeks 6–8 using the live question taxonomy gathered from provider interactions.
• Work with the GTM/Growth Lead to identify referral opportunities and the right moments to ask satisfied providers for introductions.
• Ensure all customer success operations and provider communications follow strict HIPAA requirements, especially in the context of mental health documentation and PHI handling.

Professional profile

The ideal candidate brings substantial customer success experience, including at least one prior instance of being the first CS hire or building a CS function from scratch at a SaaS company. This is not an entry-level leadership role; the hire should already have experience hiring and developing a team. Healthcare-related exposure is strongly preferred, and familiarity with mental health workflows is a meaningful advantage. The person must be fluent in PHI and HIPAA rules in practice, able to distinguish between product support issues and clinical escalation needs, and comfortable making judgment calls in ambiguous situations.

This role also requires a strong player-coach mindset: someone energized by direct customer work in the first phase, while also being motivated by the process of building systems that scale later. Comfort with AI-assisted support, ticketing tools, CS platforms, and stack selection from scratch is essential. Clear communication, empathy in sensitive conversations, and confidence using AI tools as part of everyday workflow are all key parts of success in this position.

Compensation and hiring notes

The remote pay range for this position is USD 191,500 to USD 204,000. The exact compensation structure may be discussed during the hiring process and could vary based on the role format. The company emphasizes equal opportunity hiring and follows a fair process. Interview calls and video screenings may be recorded and transcribed for consistency and bias reduction. Candidates should only expect communication through official company email addresses or the formal applicant tracking system, and sensitive personal information will only be requested through official application channels.

About the company

The employer is an all-in-one EHR+ platform focused on independent healthcare practices. The product suite is designed to simplify operations for private practices by combining EHR, billing, automation, telehealth, and marketing tools. The company supports more than 42,000 private practices and aims to help clinicians reduce admin burden, increase revenue, and spend more time with patients.

Values

• Begin with the customer: understand the needs of customers and their patients through their perspective.
• Simplify complexity: make healthcare workflows easier to navigate.
• Think entrepreneurially: approach problems with creativity, persistence, and action.
• Win as a team: stay collaborative, humble, and inclusive.
• Celebrate progress: make space for joy and shared success.

Perks and benefits

In the United States, the company provides healthcare benefits along with additional employee perks. These include a Dell discount for home office essentials, access to Gympass for fitness and wellness support, and Telus Employee Assistance Program resources for mental health and everyday life support. For Costa Rica-based employees, the benefits package also includes a wellness and childcare subsidy, a university/education discount, Gympass access, and Telus Employee Assistance Program resources.

Equal opportunity and privacy

This employer considers all qualified applicants without regard to age, race, color, religion, sex, sexual orientation, gender identity, national origin, veteran status, or disability status. California applicants are directed to review the state-specific privacy notice for additional information. Fraudulent job postings should be reported through the company’s designated talent contact and, if appropriate, to law enforcement or consumer protection agencies.