Senior Head of Digital & Scaled Customer Success – AI‑Powered, Data‑Driven Leader Driving SaaS Growth, Retention, and Customer Advocacy at brighthush

About brighthush

brighthush isn’t just another SaaS platform – it’s a movement that reimagines how teams set goals, collaborate, and bring ideas to life. By weaving together intuitive design, AI‑enhanced workflows, and an unwavering focus on customer outcomes, we empower organizations of every size—from nimble startups to global enterprises—to unlock their full potential. Our mission is simple yet ambitious: to make work smarter, faster, and more human. We achieve this by building tools that scale effortlessly, adapt to context, and learn from every interaction.

Founded in the heart of the tech ecosystem, brighthush has evolved into a distributed, fully remote powerhouse. While our headquarters sit in San Francisco, our talent spans the entire United States, and we celebrate the freedom that comes with a flexible, location‑agnostic culture. Transparency, curiosity, and data‑driven decision making are the pillars that support our culture, and we are constantly evolving to stay ahead of the curve in a fast‑moving SaaS landscape.

At brighthush, we believe that every customer interaction is an opportunity to create lasting value. Our platform is designed to empower teams to work smarter, collaborate more effectively, and achieve their goals with confidence. We are looking for a visionary leader who can take our customer success strategy to the next level, turning data into insight, insight into action, and action into measurable growth.

Position Overview

We are on the hunt for a visionary Senior Head of Digital & Scaled Customer Success to architect, launch, and continuously refine automated, data‑rich customer success programs that serve our smaller‑tier customer base. In this role, you will partner with Product, Marketing, Operations, and Data Science to create AI‑powered engagement plays, build robust metrics frameworks, and run rigorous experimentation that drives retention, engagement, and revenue growth. Your strategic vision will shape the digital customer journey, ensuring that every touchpoint is purposeful, personalized, and scalable.

Why This Role Matters

Customer success is the engine that powers SaaS growth. By turning every customer interaction into a data‑rich, AI‑enhanced experience, you’ll help brighthush convert new sign‑ups into long‑term advocates while freeing up our human teams to focus on high‑impact, complex issues. Your work will directly influence product adoption, churn reduction, and revenue expansion across millions of users worldwide.

Key Responsibilities

• Define and Own Digital Strategy – Craft the overarching digital CS strategy, mapping the end‑to‑end customer journey, and establishing engagement motions for each lifecycle stage. Translate business goals into actionable, scalable digital initiatives.
• Design Self‑Serve Success Programs – Build and launch self‑serve onboarding flows, lifecycle communications, and in‑product nudges that drive activation and habitual usage with minimal human intervention.
• Build AI‑Powered Engagement Plays – Partner with Product to develop AI‑driven automation that scales team impact. Clarify platform capabilities versus custom automation, ensuring seamless integration and measurable outcomes.
• Accelerate Time‑to‑Value – Create strategic customer plays that combine relationship building, deep discovery, and solution alignment. Serve as a trusted advisor and escalation point for complex, high‑value customers.
• Establish Metrics Frameworks – Define activation milestones, identify leading indicators, and build instrumentation to measure program success across every stage of the journey.
• Drive Data‑Informed Experimentation – Lead a rigorous experimentation program to test and refine engagement motions. Use data insights to iterate playbooks and optimize customer outcomes.
• Lead Cross‑Functional Vision – Build and mentor a high‑leverage team, while collaborating with Product, Marketing, Operations, and Data Science to align stakeholders on the digital CS vision and operating model.
• Champion Continuous Improvement – Foster a culture of experimentation, rapid iteration, and learning. Encourage the team to test hypotheses, measure results, and share insights across the organization.
• Represent Customer Success at Executive Level – Translate customer insights into strategic recommendations for senior leadership. Advocate for customer‑centric initiatives that drive long‑term business value.

Essential Qualifications

• 7–10+ years of progressive leadership in Customer Success or client‑facing roles within the SaaS industry, with a proven track record of managing large‑scale, regional organizations.
• Deep experience designing, launching, and scaling digital or programmatic customer success initiatives that drive measurable business outcomes.
• Strong analytical mindset with expertise in establishing metrics frameworks, tracking leading indicators, and running data‑driven experimentation programs.
• Proven ability to partner cross‑functionally with Product, Marketing, and Operations to create product‑led and program‑led customer journeys.
• Exceptional problem‑solving skills and a history of advising on complex customer escalations at a senior level.
• Demonstrated success in building, mentoring, and developing high‑performing teams while implementing strategic operating models.
• Excellent communication and storytelling skills, capable of translating complex data insights into actionable strategies for both technical and non‑technical stakeholders.

Preferred Qualifications

• Experience with AI tools and emerging technologies, and a passion for leveraging them to enhance productivity, collaboration, or decision‑making.
• Background in building AI‑driven engagement plays or automation workflows that scale human impact.
• Familiarity with industry‑standard experimentation platforms and statistical analysis for A/B testing.
• Experience working in a fast‑paced, high‑growth SaaS environment with a focus on customer retention and expansion.
• Strong communication skills, capable of translating complex data insights into actionable strategies for both technical and non‑technical stakeholders.

Skills & Competencies

• Strategic Thinking – Ability to see the big picture while managing day‑to‑day execution.
• Data Literacy – Proficiency in SQL, data visualization tools, and statistical analysis.
• AI & Automation Fluency – Comfortable building and iterating AI‑powered workflows.
• Leadership & Coaching – Proven track record of developing high‑performing teams and fostering a culture of continuous improvement.
• Customer‑Centric Mindset – Deep empathy for customers and a relentless drive to solve their problems.
• Project Management – Skilled at managing multiple initiatives, prioritizing effectively, and delivering on time.
• Change Management – Ability to lead organizational change, influence stakeholders, and embed new processes.

Career Growth & Learning Opportunities

At brighthush, we believe that learning is a lifelong journey. As Senior Head of Digital & Scaled Customer Success, you’ll:

• Lead a high‑visibility, cross‑functional team that directly influences product strategy and revenue.
• Collaborate with senior leaders across the organization, gaining exposure to product development, marketing, and data science.
• Own a portfolio of AI‑driven initiatives that set industry standards for customer success automation.
• Participate in executive‑level strategy sessions, shaping the future of brighthush’s customer experience.
• Access continuous learning resources, including industry conferences, workshops, and internal knowledge sharing.
• Take on mentorship roles, guiding junior leaders and fostering the next generation of customer success talent.
• Explore opportunities to transition into broader strategic roles such as Chief Customer Officer or Head of Growth.

Work Environment & Company Culture

brighthush thrives on a culture of transparency, innovation, and inclusion. We value:

• Remote flexibility – work from anywhere in the United States, with optional office days in San Francisco, Chicago, or New York City.
• Collaborative teamwork – cross‑functional collaboration is at the heart of everything we do.
• Data‑driven decision making – every initiative is backed by rigorous analysis and experimentation.
• Continuous improvement – we celebrate failures as learning opportunities and iterate quickly.
• Diversity & inclusion – we actively foster an environment where every voice is heard and respected.
• Employee well‑being – we provide resources for mental health, fitness, and work‑life balance.
• Community impact – we encourage volunteerism and support initiatives that give back to local communities.

Compensation & Benefits

While specific figures vary by role and location, we offer a competitive total compensation package that may include:

• Base salary commensurate with experience and market benchmarks.
• Performance‑based bonuses and equity opportunities.
• Health, dental, and vision insurance.
• Mental health, wellness, and fitness benefits.
• Career coaching and professional development support.
• Inclusive family‑building benefits (e.g., parental leave, adoption assistance).
• Long‑term savings or retirement plans.
• Optional in‑office culinary options for those who prefer a hybrid schedule.
• Generous paid time off, including vacation, sick leave, and personal days.
• Flexible work hours and a results‑oriented performance model.

How to Apply

If you’re ready to lead the next wave of digital customer success at brighthush, we’d love to hear from you. Submit your application through our careers portal and let’s explore how your vision and expertise can help shape the future of our customers.