Strategic Head of Customer Success – Driving Adoption, Retention, and Growth for a Remote SaaS Platform at brighthush

About brighthush

brighthush is a forward‑thinking SaaS company that empowers businesses to unlock the full potential of their digital ecosystems. With a mission to deliver measurable value through seamless customer journeys, we are redefining how organizations engage with technology, data, and people. Our platform is built on a foundation of innovation, customer obsession, and a culture that celebrates curiosity, collaboration, and continuous improvement.

Why Join brighthush?

As a remote‑first organization, brighthush offers the flexibility to work from anywhere in the United States while fostering a vibrant, inclusive, and high‑energy work environment. We invest heavily in our people, providing competitive equity, comprehensive health benefits, generous paid time off, and a robust learning & development budget. Our team is passionate about solving complex problems, and we celebrate every milestone—whether it’s a successful customer launch, a breakthrough feature, or a personal achievement.

Position Overview

We are seeking an ambitious, results‑driven Head of Customer Success to lead the entire customer success function for brighthush’s flagship SaaS platform. In this role, you will own the end‑to‑end customer journey—from onboarding and adoption to retention and expansion—while building and scaling a high‑performance Customer Success team. Your strategic vision, data‑driven mindset, and hands‑on execution will directly impact our growth trajectory and customer satisfaction.

Key Responsibilities

• Onboarding Excellence: Design and execute a structured onboarding roadmap that transforms signed contracts into steady‑state usage. Define clear milestones, time‑to‑first‑ROI, and time‑to‑value metrics, ensuring every new customer experiences a smooth, value‑driven launch.
• Sales‑to‑CS Handoff: Lead a meticulous handoff process that coordinates launch activities across data migration, user setup, approval rules, shop coverage, and integrations with fleet systems, telematics, and ERP platforms.
• Adoption & Gap Analysis: Define “adopted” for each customer segment, identify gaps between contracted scope and actual usage, and collaborate with Operations and the shop network team to close those gaps.
• Operational Business Reviews: Conduct data‑rich business reviews that showcase tangible value—cycle time reduction, cost per repair, downtime, and savings—using customers’ own metrics.
• Account Health Model: Build a sophisticated health scoring system with leading indicators, risk thresholds, and playbooks. Execute proactive save plans for at‑risk accounts and drive continuous improvement.
• Churn Analysis & Product Feedback: Lead monthly cross‑functional churn reviews, transform churn causes into a prioritized list of product and operational fixes, and advocate for customer‑centric enhancements.
• Team Leadership & Scaling: Hire, mentor, and grow a team of Customer Success Managers (CSMs). Design coverage models by segment, establish operating systems within our CRM, and cultivate a culture of accountability and collaboration.
• Reporting & Stakeholder Management: Provide monthly insights to the CRO and executive leadership on retention, utilization, time‑to‑value, and account health, translating data into actionable business decisions.

Essential Qualifications

• 7+ years of progressive experience in Customer Success at a B2B SaaS company, with a proven track record of improving retention and adoption.
• Demonstrated ability to build or scale a CS function from scratch, including health scoring, playbooks, segmentation, coverage models, and CRM implementation.
• Experience managing usage‑based or transaction‑based revenue models, with a deep understanding of how customer behavior drives revenue.
• Hands‑on experience with AI tools that automate routine CS tasks and extend CSM coverage.
• Strong project management skills, capable of coordinating multi‑site implementations with numerous stakeholders.
• Data‑savvy mindset: proficiency in extracting, analyzing, and interpreting usage data to spot slipping accounts and guide customers through their own metrics.
• Willingness to serve as a player‑coach initially—directly owning onboarding and key accounts while building the team.

Preferred Qualifications

• Background in the automotive, fleet, or insurance technology space.
• Experience with large‑scale integrations (e.g., telematics, ERP, fleet management systems).
• Prior success in a high‑growth startup environment, navigating rapid scaling and evolving customer needs.
• Advanced knowledge of customer success platforms (e.g., Gainsight, Totango, ChurnZero) and CRM systems (e.g., Salesforce, HubSpot).
• Strong communication skills, with the ability to translate complex data into compelling narratives for both technical and non‑technical audiences.

Core Competencies

• Strategic Vision: Ability to translate business goals into actionable CS strategies.
• Customer Obsession: Deep empathy for customers and a relentless focus on delivering value.
• Analytical Acumen: Proficiency in data analysis, KPI development, and performance measurement.
• Leadership & Coaching: Proven talent for building high‑performing teams and fostering a culture of growth.
• Project Management: Expertise in managing complex, cross‑functional initiatives.
• Adaptability: Comfortable navigating ambiguity and driving change in a fast‑paced environment.

Career Growth & Learning Opportunities

At brighthush, your professional development is a top priority. You will have access to:

• Annual learning & development budget for courses, certifications, and conferences.
• Mentorship from senior leaders across product, engineering, and sales.
• Clear career pathways—from Customer Success Manager to Director, VP, and beyond.
• Opportunities to influence product strategy, go‑to‑market initiatives, and company culture.

Work Environment & Culture

Our remote‑first culture is built on trust, transparency, and collaboration. We celebrate diversity and inclusion, and we encourage every team member to bring their authentic self to work. Key cultural pillars include:

• Weekly virtual town halls and cross‑functional “innovation sprints.”
• Monthly hackathons where teams prototype new features or process improvements.
• Open‑door policy: leaders are accessible and receptive to feedback.
• Community outreach programs and volunteer days.

Compensation & Benefits

While specific figures vary based on experience, the overall package includes:

• Competitive base salary commensurate with market rates for senior CS leaders.
• Performance‑based bonus tied to retention, adoption, and customer satisfaction metrics.
• Equity stake in brighthush, aligning your success with the company’s growth.
• Comprehensive medical, dental, and vision coverage for you and your dependents.
• Flexible paid time off (PTO) and company holidays.
• Home office stipend and equipment support to create an optimal remote workspace.
• Wellness stipend for gym memberships, mental health resources, or other personal well‑being initiatives.
• Paid parental leave and family‑friendly policies.

How to Apply

If you are a visionary leader who thrives on building high‑impact teams, driving customer success, and shaping the future of SaaS, we want to hear from you. Submit your resume, a cover letter detailing your most significant CS achievements, and any relevant metrics that showcase your impact.

Join brighthush and help us create a world where customers not only adopt our platform but become lifelong partners in success.