Director, Customer Retention

HighLevel

1d•Remote

About The Position

HighLevel is an AI-powered business operating system that gives agencies, entrepreneurs and SMBs the infrastructure to build, automate and scale. Today, HighLevel supports SMBs across 150+ countries, fueling community-driven growth rooted in real customer outcomes. To date, businesses operating on HighLevel have generated over $7 billion in ecosystem value, demonstrating the impact of shared infrastructure at scale. By centralizing conversations, automation and intelligence into one system, we help businesses move faster, reduce complexity and execute efficiently. Behind the platform, HighLevel powers more than 4 billion API hits and 2.5 billion message events daily. With 250 terabytes of distributed data, 250+ microservices and over 1 million domain names supported, our architecture is built for performance, resilience and long-term scalability. HighLevel operates as a global, remote-first organization built for speed and ownership with over 2,000 team members across 10+ countries. We value initiative, clarity and execution, creating space for ambitious people to build systems that support millions of businesses worldwide. Here, innovation thrives, ideas are celebrated and people come first, no matter where they call home. Every month, HighLevel enables more than 1.5 billion messages, 200 million leads and 20 million conversations for the more than 1 million businesses we support. Behind those numbers are real people building independence, expanding opportunity and creating measurable impact. The Director, Customer Retention will lead and evolve HighLevel’s retention engine across early adoption, de-escalation, frontline care, and customer value realization. This role will partner closely with cross-functional teams to ensure customers achieve success in their first 90 days — the most critical driver of long-term retention. The ideal candidate thrives in high-growth environments, takes ownership of customer outcomes, and operates with a balanced mindset of strategy, operational excellence, and people leadership.

Requirements

12+ of experience, a proven track record of improving Gross & Net Revenue Retention in a SaaS environment, with clear playbooks that moved the needle (early adoption, de-escalation, save motions, product activation).
5+ years managing managers, with proven success leading large teams of 20+ people.
Demonstrated ability to transform reactive support or care teams into proactive, retention-driven organizations.
Expert at turning reactive support environments into proactive revenue-saving teams, with measurable reductions in involuntary and voluntary churn.
Strong commercial mindset — understands plan mix, cohort behavior, discount impact, and how customer experience directly influences revenue outcomes.
Deep fluency in early lifecycle metrics (activation, onboarding milestones, first-value attainment) and how these correlate to long-term retention and expansion.
Proven experience building de-escalation frameworks, early adoption programs, or churn reduction initiatives with measurable results.
Strong operational mindset with expertise in SOP development, process improvement, and scaling through systems and tooling.
Exceptional coaching ability — you build leaders who build strong teams.
Strong collaboration and stakeholder management skills across product, marketing, success, support, and operations.
Highly analytical, data-driven, and able to translate insights into actionable strategies.
Positive, resilient, and passionate about helping customers achieve long-term success.
Bachelor’s degree in Business, Communications, Management, or a related field (or equivalent practical experience).

Nice To Haves

MBA or advanced degree preferred but not required.

Responsibilities

Lead and oversee 3 Customer Care/Retention teams (40+ members) focused on proactive resolution, engagement, and churn prevention.
Rebuild the org from "Customer Care" into a Retention & De-Escalation Center designed to protect revenue and reduce churn at scale.
Create and operationalize retention frameworks that eliminate friction, close expectation gaps, and accelerate adoption.
Drive early activation, onboarding success, and value realization across the first 90 days, the period most correlated with long-term retention.
Identify customer-risk patterns early and design playbooks that trigger proactive outreach before churn happens.
Ensure the team is skilled and certified in all onboarding SOPs, including KO Calls and Implementation Calls.
Partner with Customer Success, Account Management, Support, Product, and Marketing to create a seamless, retention-driven customer journey.
Translate frontline insights into product improvements, experience fixes, and revenue-impacting initiatives.
Influence product roadmap decisions through customer insights, patterns, and root-cause analysis from frontline interactions.
Own and run a revenue-retention operating model with clear KPIs tied to gross retention, save rate, activation milestones, and churn attribution.
Own and improve the metrics that matter, including: Net Revenue Retention, Early adoption rates, Escalation deflection.
Establish a performance system that measures and improves the quality, coverage, and speed of customer save motions and optimizes capacity and routing models so the highest-revenue and highest-risk customers receive prioritized attention.
Standardize SOPs, documentation, and workflows that allow retention operations to scale efficiently.
Implement forecasting discipline for churn and saves, improving visibility of revenue risk and enabling proactive interventions.
Champion automation and process innovations that reduce manual effort and improve customer outcomes.
Lead, coach, and develop frontline managers and team leads — building a leadership bench that can scale with the org.
Foster a culture of high accountability, continuous improvement, and customer-centric problem solving.
Own capacity planning, staffing forecasts, and headcount alignment to support organizational growth.