Director of Customer Success

The Role 

This is a player-coach role for someone who wants to build Crystal's Customer Success function and the team that runs it. You'll report to the VP of Customer Experience, own retention and growth across our post-sale customer base, and personally carry the high-touch accounts that matter most: newly onboarded practices and the ones at risk of churning. 

You won't inherit a 20-person org or a polished playbook. There isn't one yet. You'll write it: health scoring, renewal plays, success plans, business reviews, and the coverage model that tells us how many CSMs we need and where. You'd rather run a save call yourself on Tuesday and coach a new CSM through their first renewal on Thursday than present a strategy deck about either. 

You'll build the team with a mix of experienced CSMs from outside and people from inside. Some of Crystal's best future CSMs are already here, answering support tickets and training practices on the platform. You'll hire the right outside talent and design the path that turns a hungry support rep or trainer into a Jr CSM, then a CSM who owns a book. You'll be judged on how well the whole team performs. 

What Success in This Role Looks Like 

• You've protected the base. GRR is up and renewals land on time. Churn doesn't surprise anyone, because at-risk accounts had a save plan months before the contract date. • You've built a strong bench. You've hired strong CSMs from outside and stood up a Jr CSM pathway for internal promotions.. 

• You've grown the accounts. Your team spots new offices, adds doctors and staff, and product attach, then hands Sales a deal that's already diagnosed. 

•You've shipped a playbook people actually use. Health scoring, renewal plays, success plans, and QBR templates live in Salesforce and get used every week. If you took a month off, the team would keep running. 

• Practices can prove the value. Strategic accounts have a before-and-after story on a workflow or financial metric, and adoption of products, integrations, and services is climbing across the book. 

• Leadership trusts your number. The VP of Customer Experience and the board trust your renewal forecast, and you can tell the story behind every dollar of churn and expansion.

Qualifications 

• 7+ years in Customer Success or Account Management in B2B SaaS, including at least 2 years leading or player-coaching a CS team. 

• A track record of hiring experienced CSMs and developing people into CS roles from Support, Training, or Implementation. You've built a ramp program and can point to the people it produced. 

• Personal ownership of renewals and expansion, with GRR and NRR numbers to show for it. Not a leader who only manages the dashboard. You can still run a renewal negotiation and a termination conversation yourself. 

• Experience building CS infrastructure from scratch: health scoring, segmentation and coverage models, success plans, renewal playbooks, and QBR cadences. 

• SMB or mid-market vertical SaaS experience. Healthcare, optometry, ophthalmology, EMR, payments, or revenue cycle experience is a strong plus. 

• Salesforce proficiency and comfort building the reports you forecast from. • Active AI leverage. You use AI tools daily, try new capabilities as they emerge, and look for ways to automate account prep, outreach, and reporting so a small team can cover a big book.

Personal Attributes 

• Talent scout with a high bar. You see a future CSM in the support rep who always goes one step further, and you'll still tell them plainly when it isn't working. 

• Player-coach, emphasis on both. You'll run the hardest renewal on the board, then debrief it with your newest CSM the same afternoon. 

• Commercially unafraid. Price increases, terminations, and churn calls don't make you flinch. You'd rather have the hard conversation in March than explain a lost renewal in June. • Builder who writes it down. If it only works because you're in the room, you haven't built it yet. 

• Knows enough to be dangerous. Deep enough across EHR, billing, scheduling, and payments to diagnose the problem, and humble enough to bring in the expert to solve it.

Benefits 

• Competitive compensation based on experience 

• Health, dental and vision benefits 

• Hybrid work flexibility with in-office collaboration in Austin 

• 401(k) with matching company contribution 

• Flexible PTO policy 

• Ground-floor opportunity in a well-funded, fast-growing healthcare technology company 

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.