Director, Payments

This is a fully remote position, open to applicants in California.

📋 Description

• Take charge of and enhance the go-to-market strategy, operational model, and revenue performance for CARET Pay.

• Oversee the payments operating model and profit and loss (P&L) management.

• Implement weekly onboarding and activation reviews, monthly cross-functional business assessments, and quarterly executive updates.

• Manage the comprehensive payments performance, including net revenue, processed volume, net spread, merchant activation, and merchant retention.

• Create accountability, standard operating procedures (SOPs), and guidelines for engagement across Sales, Payments, Implementation, Training, and Customer Success.

• Handle merchant onboarding for both new logo and migration deals.

• Minimize merchant application friction and enhance underwriting-stipulation resolution.

• Assess payments fit at the point of sale and ensure payments sellers connect with prospects during the LPM sale.

• Formulate account-level strategies for complex customers in collaboration with Sales, Customer Success Managers (CSMs), and Migration.

• Promote the adoption of invoicing and accounting workflows within practice management products.

• Segment the existing customer base, create named-account strategies, and provide personalized onboarding for significant activation opportunities.

• Implement 30- and 60-day post-go-live transaction follow-ups.

• Develop the processor-switching toolkit in conjunction with Marketing and evaluate switching incentives with Finance.

• Identify causes of processor reversion and prioritize product enhancements with the Product and Engineering teams.

• Collaborate with Sales and Go-To-Market (GTM) leadership on the wider B2B commercial strategy.

• Lead, mentor, and develop the payments team.

• Design payments quotas, compensation schemes, and referral incentives alongside Sales leadership and Finance.

• Define and track payments metrics while establishing CRM and Business Intelligence (BI) reporting.

• Manage pricing, fee schedules, promotional economics, and the mix between ACH and card payment methods with Finance.

• Safeguard existing revenue by monitoring merchant concentration, volume declines, and shifts in processors.

• Oversee relationships with payment-processing and payment-facilitator partners.

• Collaborate with Legal, Finance, Risk, and Compliance on agreements, payment structures, and commercial terms.

• Keep abreast of card network regulations, PCI obligations, ACH requirements, and trust-account handling rules.

⛳️ Requirements

• Minimum of 10 years' experience in B2B payments, fintech, or SaaS.

• At least 3 years of experience leading a payments function or a cross-functional payments go-to-market initiative.

• Proven experience owning or leading integrated or embedded payments within a software/SaaS context.

• Familiarity with the complete lifecycle from onboarding and migration to ongoing performance.

• Demonstrated ability to collaborate cross-functionally with Sales, Customer Success, Product, Engineering, Operations, Finance, and Legal.

• Strong operational capabilities combined with strategic vision.

• Exceptional analytical skills, including customer segmentation, cohort analysis, and unit economics evaluation.

• Strong commercial acumen and executive presence.

• Ability to influence others without direct authority.

• Experience presenting to both customers and the executive team.

• Proven track record of enhancing merchant boarding, activation, or attach quality in an embedded payments environment.

• Experience in successfully diverting volume from incumbent processors.

• Working knowledge of interchange, ACH versus card, net spread, pricing, and promotional structures.

• Experience in hiring, coaching, and managing a small team of sales representatives and operators.

• B2B experience is essential.

• Preferred: Experience leading payments for a B2B SaaS or vertical software organization.

• Preferred: Experience overseeing customer migrations between payment providers or payment infrastructure.

• Preferred: Experience managing a payment facilitator or processor relationship.

• Preferred: Familiarity with law firm billing, trust/IOLTA, and multi-trust account requirements.

• Preferred: Proficiency in Salesforce, BI dashboards, in-app engagement tools, conversation intelligence, and implementation platforms.

🏝️ Benefits

• Flexible Paid Time Off (PTO).

• Comprehensive Medical, Dental, Vision, Paid Sick Days, and Supplemental Coverage.

• Health Savings Account (HSA).

• 401(k) matching program.