Why This Job is Featured on The SaaS Jobs
FirmPilot sits in a modern corner of SaaS where generative AI is embedded in the product’s day to day value, and where outcomes are measured in customer performance rather than software usage alone. A Customer Success leader in this context operates at the intersection of product capability, measurable marketing impact, and executive level stakeholder management, which is increasingly common across vertical SaaS and AI enabled platforms.
The role stands out for its emphasis on retention mechanics and the infrastructure behind them. Building playbooks, health signals, and intervention workflows maps directly to how SaaS businesses mature their post sale motion as they scale. Experience partnering with Product, Engineering, and Marketing to close feedback loops is also highly portable across SaaS, especially for professionals aiming to move into broader revenue leadership or CS operations ownership over time.
This position is best suited to a practitioner leader who prefers a player coach model and is comfortable switching between team development, process design, and hands on work with high value accounts. It will fit someone motivated by clear accountability around renewal outcomes and interested in translating technical product capabilities into business level narratives for senior customers.
The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.
Job Description
FirmPilot is the first generative AI platform built specifically to power modern marketing for law firms. We drive real outcomes through intelligent automation, data driven SEO, and performance focused content strategies. Our customers range from small law firms to established practices that need smarter, faster, and more scalable marketing. We are backed by top tier investors and are growing quickly.
We are building a team of high performers who take ownership, move fast, and expect to make an impact. This is a company where high agency is the expectation, hard work is the baseline, and results matter. If you want to build something meaningful at a company that operates with urgency, this is the place.
About the Role
We are hiring a Director of Customer Success to lead and scale our Customer Success organization. This is a player coach role for someone who understands what it takes to build and operate a retention focused CS function at a growth stage company.
You will inherit a team of Customer Success Managers, with plans to continue growing the team over the next year. Approximately two thirds of your time will be spent building and refining the systems, playbooks, and processes that drive customer outcomes and retention. The remaining time will be spent directly owning and supporting high value accounts.
Gross Dollar Retention is a core focus for 2026, and this role will be central to achieving that goal.
This is not a hands off leadership role. We are looking for someone who can lead strategic conversations with senior clients, coach CSMs through complex renewals, and build scalable infrastructure all within the same week. You will report to the VP of Customer Success and play a key role in shaping how the CS organization evolves as FirmPilot scales.
What You Will Do
- Lead, coach, and develop a team of Customer Success Managers, including hiring as the team grows
- Personally own a portfolio of high priority accounts and act as a strategic advisor and executive sponsor
- Build and refine Customer Success playbooks, processes, and systems that drive retention, adoption, and expansion
- Establish and monitor leading indicators of churn risk and ensure proactive intervention
- Partner closely with Product, Engineering, and Marketing to improve customer outcomes and close feedback loops
- Drive accountability across the team for activation milestones, health metrics, and retention goals
- Create a culture of ownership, urgency, and results within the Customer Success organization
- Translate platform capabilities, AI features, and marketing strategy into clear business outcomes for law firm leadership
- Identify patterns across accounts to inform product roadmap and go to market decisions
What You Bring
- Five or more years of experience in Customer Success, including at least two years managing and developing CSMs
- A proven track record of scaling Customer Success at growth stage startups
- Strong operational experience building or refining CS playbooks, health scoring, and retention focused processes
- Demonstrated success improving retention metrics and a clear understanding of the drivers behind Gross Dollar Retention
- Ability to operate as a player coach, balancing leadership responsibilities with hands on account ownership
- Strong executive presence and the ability to build trust with demanding customers
- Clear, confident communication skills and the ability to explain technical or strategic concepts to non technical audiences
- High agency, strong follow through, and a bias toward action
- Comfort operating in fast paced, ambiguous environments with high accountability
Nice to Have
- Experience in legal tech, professional services, or marketing technology
- Familiarity with AI driven products or companies where AI is core to the value proposition
- Experience with Customer Success platforms such as Gainsight, ChurnZero, or Vitally
- Exposure to digital marketing concepts including SEO, paid media, and content strategy
What We Offer
- Competitive compensation
- Health and dental benefits
- Direct access to leadership and real ownership over your work
- Career growth as the company and Customer Success organization scale
- The opportunity to build something meaningful where your impact is immediate
- A culture built on high standards, accountability, and winning
In compliance with applicable pay transparency and good faith estimate requirements, this role has an estimated annual base salary range of $140,000 to $157,000.
Compensation will be determined based on experience, skills, location, and internal equity.
