Director of Customer Success

About Billables AI

Billables AI is building the AI-powered operating layer for professional service firms, and we're starting where the pain is deepest: the legal industry. Our platform automates the manual overhead that slows lawyers down, bringing together intelligent timekeeping, work activity capture, and operational visibility so firms can understand how work happens and build a more efficient, profitable practice. The best work happens when people aren't buried in administrative burden, and that's exactly the problem we're solving.

Named Legal Tech Company of the Year by Law.com in 2026, Billables AI is one of the fastest-growing companies at the intersection of AI and legal technology. Our team brings together expert AI researchers and veteran startup builders who know how to move fast, build with conviction, and deliver software that sits at the core of how our customers work and generate revenue. Based in San Francisco, we empower everyone on the team to drive meaningful work end-to-end.

About the role

This role owns the full post-sale relationship — every law firm account from go-live through renewal — and runs the first line of support for those firms.

Because CS has been fundamental to Billables AI from the beginning, you’re inheriting real infrastructure, not a blank page: a support platform and knowledge base, ticketing and triage workflows, account health and seat data, a structured onboarding and ramp program, partner enablement materials, and the foundations of a Customer Advisory Board. Your job is to take all of it from functional to durable — and to do it at the pace of a company that’s doubling.

This is a player-coach role. For the next stretch you’ll carry accounts and run escalations yourself while you build the team and systems that carry the function as it scales. It’s a build-and-operate role for someone who wants to stay close to the work — hands on the accounts and the systems, not just the org chart.

What you’ll own

Accounts and revenue. You own a book of law firm accounts end to end — adoption, seat expansion, renewals, and the multi-year and annual-term conversations, including moving month-to-month accounts onto annual terms. You’ll forecast renewals, spot churn risk early, and hold a clear segmentation model for where to invest — which accounts warrant high-touch coverage and which are best served through scaled, lower-touch motions.

Implementation and integration. You own the implementation function — the standards for configuration, validation, and go-live readiness, and the managers you hold to them. Because Billables AI depends on a third-party practice management system working correctly, you’ll oversee technical triage and have the fluency to step in and lead a resolution from the inside when an account needs it. You’ll own escalation strategy across our practice management partnerships, bringing the firm, the partner, and our engineering team onto a single path.

Support operations. You’re the ultimate owner of support — routing, SLAs, knowledge base, and AI agent strategy — with a support operator running the day-to-day. You’ll define what our reporting has to answer (where issues cluster by account, partner, and root cause) and turn those signals into product priorities. The goal is to reduce ticket volume structurally, not to work the queue harder.

Partners, team, and cross-functional leadership. You own the CS side of our practice management partnerships — training partner CSMs to position and support Billables AI, joint onboarding, co-branded enablement — as a true operational counterpart, not just an escalation contact. You’ll build a real working relationship with Sales (clean handoffs, shared context, a unified front with the customer), be the credible CS voice with product and engineering, and represent the customer base to leadership with an evidence-backed point of view. And you’ll hire, ramp, and develop the CS team, building the playbooks and documentation that make the function repeatable.

What we’re looking for

• You’ve built or scaled a CS function from functional to durable — ideally at an early-stage company, across mid-market and enterprise segments.

• You’ve led and grown a customer-facing team — hiring, ramping, and developing people into full ownership of their own books or functions.

• You’re a self-starter with an entrepreneurial streak. You work well under pressure, make fast but informed decisions, and hold strategy and execution at the same time without dropping either. Our accounts are high-volume and high-intensity, and priorities shift.

• 5+ years in customer success, implementation, or account management in B2B SaaS, with at least 2 years owning renewals or expansion — and experience at a company where CS carried direct revenue responsibility.

• Strong judgment about where to spend effort. Some accounts will ask for more than their contract justifies, and you’ll know the difference.

• Strategic communication across a wide range of stakeholders — billing managers to managing partners to your own leadership — and the instinct to build a partnership with Sales rather than a handoff.

• Technical fluency. You won’t write production code, but you’re comfortable with APIs, authentication concepts, field mapping, and data validation, and you can read enough of an error to know what you’re looking at. Bonus: you’ve owned integrations or implementations that depend on a third-party system working correctly.

• Excellent written communication — especially the ability to explain a technical failure to a non-technical stakeholder without minimizing it or over-promising the fix.

  
  

Strongly preferred

• Legal technology experience, or direct experience with law firm billing and timekeeping workflows. Our customers value talking to someone who understands how their business runs — but we’ll back the right builder to ramp fast on the domain.

• Familiarity with practice management platforms such as Centerbase, Litify, SurePoint, Clio, Orion, Juris, or LeanLaw.

• Experience managing a channel or platform partnership from the post-sale side.