[Hiring] Director, Payments @CARET

Role Description

We’re looking for a Director, Payments to own and scale the go to market strategy, operating model, and revenue performance of CARET Pay, our integrated payments product embedded in the legal practice management (LPM) software our customers run their firms on. This is a highly cross functional role at the intersection of payments, sales, customer success, implementation, product, finance, and legal.

CARET Pay is one of our fastest growing revenue lines, and the next phase of growth depends on attaching and activating new customers as well as the installed base. Unlock that growth by working cross functionally to ensure customers adopt invoicing capabilities within our LPM solution and displace incumbent payment processors. This role owns the full attach, boarding, activation, expansion, and retention journey.

This is a hands on role: you should be as comfortable setting strategy as working directly with prospects and customers to board, activate, and grow specific accounts.

What You’ll Do

• Own the payments operating model and P&L
  • Develop and own the strategy and operating cadence for our payments business, including weekly boarding and activation reviews, monthly cross functional business reviews, and quarterly executive updates.
  • Own end to end payments performance and the CARET Pay P&L: net revenue, processed volume, net spread, merchant activation, and merchant retention.
  • Establish clear accountability, documented SOPs, and rules of engagement across Sales, Payments, Implementation, Training, and Customer Success.
• Scale boarding and activation
  • Own merchant boarding end to end and carry a boarding rate target for both new logo and migration deals.
  • Reduce merchant application friction: fewer fields, CRM pre-fill, modern bank connection, and fast resolution of underwriting stipulations.
  • Qualify fit at the point of sale so attach reflects a customer’s genuine intention to process rather than an order form default, and ensure payments sellers engage prospects during the LPM sale.
  • Own account-level strategies for complex customers with Sales, CSMs, and Migration, identifying blockers, sequencing work, and coordinating internal stakeholders, and getting personally involved where hands on leadership is required.
  • Drive adoption of the invoicing and accounting workflows inside our practice management products.
  • Segment the installed base into a payments ICP and priority tiers, then build named account plays and concierge onboarding for the largest activation opportunities while protecting the top volume generating merchants.
  • Stand up structured post go live follow ups — 30 and 60 day first transaction checkpoints with alerts when a merchant is not processing.
• Win the processor switch
  • Build the switching toolkit with Marketing, including competitor comparisons and savings calculators, customer proof points, in app prompts, and outbound campaigns timed to product releases, and test switching incentives with Finance.
  • Diagnose why merchants revert to a competing processor and turn those reasons into a prioritized product backlog with Product and Engineering: feature parity, reconciliation and reporting reliability, trust accounting support, and recurring billing.
• Partner across GTM and lead the team
  • Work closely with Sales and GTM leadership to incorporate payments into the broader B2B commercial strategy.
  • Lead, coach, and grow the payments team, and design payments quotas, compensation plans, and referral incentives with Sales leadership and Finance so payments outcomes are owned by the teams closest to the customer.
• Own and improve payments performance
  • Define and monitor the metrics that matter: attach rate and attach quality, merchant boarding rate, time from signature to first transaction, activation and inactive-merchant rates, penetration, processed volume, net spread, and retention — and build the CRM and BI reporting that makes them visible to every seller, CSM, and executive.
  • Own pricing, fee schedules, and promotional economics with Finance, including the ACH-versus-card mix that drives net spread.
  • Protect existing revenue: monitor concentration among the largest merchants, detect volume declines and processor shifts early, and intervene before they become churn.
• Manage payment partners, risk, and commercial requirements
  • Partner closely with Legal, Finance, Risk, Compliance, and other stakeholders on customer agreements, payment structures, and commercial terms, bringing strong judgment where customer needs, commercial objectives, and contractual considerations intersect.
  • Own the relationship with our payment processing and payment facilitator partners: commercial terms, underwriting and merchant onboarding requirements, service levels, incentive arrangements, and roadmap, plus merchant account lifecycle governance.
  • Stay current on card network rules, PCI obligations, ACH requirements, and the trust account handling rules our customers are bound by.

Qualifications

• 10+ years of experience in B2B payments, fintech, or SaaS, including at least 3 years leading a payments function or a cross functional payments go to market motion.
• Experience owning or leading integrated or embedded payments within a software/SaaS environment, ideally where payments attach to a billing or invoicing workflow inside the product, across the full lifecycle from onboarding and migration through ongoing performance.
• Proven ability to work cross functionally with Sales, Customer Success, Product, Engineering, Operations, Finance, and Legal, and to turn ambiguous, complex processes into scalable operating models.
• A hands on operator who is willing to roll up their sleeves and personally solve problems when needed, with the strategic range to set a long term vision — and the willingness to own outcomes that depend on adoption of the core software product, not only payments.
• Excellent analytical skills — you can partner with Finance on customer segmentation, cohort, and unit economics analysis, then turn it into a prioritized plan.
• Strong commercial judgment and executive presence, with the ability to influence without direct authority, including experience presenting to customers and the executive team.
• A track record of moving a payments funnel, including measurable improvement in merchant boarding, activation, or attach quality in an embedded payments business, and experience winning volume away from incumbent processors.
• Working knowledge of payments economics: interchange, ACH vs card, net spread, pricing, and promotional structures.
• Experience hiring, coaching, and managing a small team of sellers and operators.

Preferred Experience

• Experience leading payments for a B2B SaaS or vertical software company, ideally one serving professional services firms such as legal, accounting, or healthcare — integrated, embedded, or software led payments rather than terminal/POS environments.
• Experience leading customer migrations between payment providers or payment infrastructure, and managing a payment facilitator or processor relationship including underwriting, merchant account lifecycle, and revenue share economics.
• Familiarity with how law firms bill and get paid, including trust/IOLTA and multi-trust account requirements.
• Fluency with the tooling this role runs on: CRM (Salesforce), BI dashboards, in app engagement tooling, conversation intelligence, and implementation platforms.

Compensation

Base salary range: $170,000 – $200,000, plus [variable compensation] tied to CARET Pay revenue and activation targets. Actual base pay within the range depends on location, experience, and qualifications.

Benefits

• Flexible PTO
• Medical, Dental, Vision, Paid Sick Days, and Supplemental Coverage
• Health Savings Account
• 401(k) match

Equal Employment Opportunity

CARET is an Equal Opportunity, Affirmative Action Employer. The compensation information above is provided in compliance with job posting disclosure requirements. Actual base pay will depend on varying circumstances including position, location, individual qualifications, and other business needs. Depending on the position, compensation may also include bonuses or other variable pay components.