Role Overview

Our client is looking for a high-caliber Director of Customer Support and Success to lead their end to end customer journey—from low touch acquisition, onboarding and support to product adoption and retention. In this strategic and hands-on role, you’ll design and scale PLG-driven onboarding and support workflows that enable seamless customer acquisition, trial success, and long-term satisfaction, all while driving efficiency and maintaining their high bar for customer interaction quality.

This person will own the full customer success lifecycle and help turn our client into a customer-centric powerhouse—where product, support, and success align to create delightful, efficient experiences at scale.

Key Responsibilities

Build and scale PLG motions that enable low-touch, efficient onboarding and support—while retaining room for high-touch engagement when needed.
Own the full customer journey post-lead qualification—from trial activation and onboarding through support, retention, and (eventually) expansion.
Reporting to the CEO, you will be responsible for onboarding, external contact, and customer support, ensuring exceptional coverage, response quality, and trial conversion.
Oversee lead review operations, including submission approval workflows and qualification criteria (currently approving ~43%).
Manage a 30-day trial journey, ensuring potential customers are successfully onboarded and can prove out the value of the product—without pressure to convert prematurely.
Maintain structured communication protocols—support delivered through designated channels and tiers, never via direct contact or email.
Define and maintain strict processes, SOPs, and SLAs for all touchpoints, including onboarding calls, support channels, and self-serve resources.
Monitor customer health, identify churn risks early, and develop interventions to increase trial conversion, retention, and satisfaction.
Create scalable systems for tracking and reporting on KPIs, team performance, and customer lifecycle metrics to inform strategic decisions and budget planning.
Collaborate with leadership to drive usage, feedback loops, and process improvement.
Design and implement future success workflows for expansion, contraction, and multi-account management across enterprise clients (e.g., distributed resort networks).

Ideal Candidate Profile

Experience & Skills

5+ years of experience in customer success, onboarding, or support, preferably in SaaS or PLG environments
Proven track record of designing and scaling low-touch/high-efficiency onboarding and support programs
Experience managing trial-driven sales processes, particularly where customer fit is evaluated before conversion
Strong background in process design, team building, and cross-functional collaboration
Deeply analytical and operational—fluent in metrics, reporting, and data-driven decision-making
Prior experience working in early-stage, PLG, fast-growth environments where autonomy and ownership are key
Excellent communication and strategic thinking skills; comfortable presenting to C-suite

Mindset & Approach

Highly customer-obsessed, with a sharp eye for quality and detail
A first-principles thinker who solves problems with logic, creativity, and structure
Entrepreneurial and self-directed—this is a build-and-own role, not an inherit-and-maintain job
Comfortable working with evolving tools, playbooks, and systems—and ready to define them from scratch
Strong strategic vision, with the ability to zoom in on tactical execution and zoom out to long-term growth

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Director of Customer Success and Support

Director of Customer Success and Support