Head of Customer Success (Fractional, Contract)

Location: Remote

Time Zone: EST

Position: Part-time (20+ hours/week)

Dobbin is an AI-powered thinking partner that helps leaders and their teams get stuff done. We’re looking for a Head of Customer Success to lead a contract engagement for approximately 4.5 months, covering a personal leave. Your mission is to activate and guide our customers. You will partner with senior executives across a mix of industries and company types, moving them from tactical AI usage to strategic business transformation.

This is not about managing tickets or checking boxes. It is about helping leaders and teams unlock the full potential of their company’s unique expertise. You will help them see how Dobbin can go beyond simple tasks to power executive decision-making, drive team alignment, and build a living library of their strategic know-how. You will be both a strategist and an operator, building the scalable infrastructure for customer success while delivering the high-touch, consultative guidance our partners value.

You will collaborate closely with our leadership and cross-functional partners to design activation frameworks, prevent churn, and prove that making implicit knowledge explicit transforms how leadership teams work. Your success will be measured by customer activation rates, feature adoption, and your ability to build systems that scale beyond founder-led support.

What You’ll Do:

• Lead Strategic Onboarding: Guide new customers from a cold start to their first "aha" moment using fast-paced, hands-on workflows that focus on concrete wins, not abstract concepts.
• Manage a Portfolio of Key Accounts: Own the success of priority accounts, including enterprise prospects, high-engagement users, and churn-risk customers across multiple simultaneous onboardings.
• Build & Monitor Customer Health: Develop sophisticated tracking systems that enable predictive health scoring and behavioral segmentation beyond traditional firmographics.
• Become a Dobbin Power User & Teach What You Practice: Master the platform first, then teach customers the exact workflows you use to turn ideas into action.
• Drive Feature Adoption: Launch targeted campaigns to drive strategic usage of underutilized features, helping customers get the most from the platform.
• Refine Frameworks for Scalability: Continuously improve our onboarding and value-communication playbooks, learning and updating them in real time based on customer interactions.
• Partner Across the Business: Work closely with Sales, Product, and leadership to align customer insights with product development and sales strategy.

What You’ll Bring:

• Experience: 5+ years in customer success leadership, ideally with some experience in brand strategy or ecommerce. A proven track record of partnering with senior executives on strategic initiatives is essential.
• Strategic + Operational Balance: You have a history of building frameworks and infrastructure while also doing hands-on customer work.
• Technical Aptitude: You understand AI-powered tools, master complex software platforms quickly, and can teach them to others in a simple, human way.
• Customer-focused Empathy: You have a deep empathy for senior executives who need to capture and scale their strategic thinking across teams.
• Exceptional Communication Skills: You excel at meeting customers where they are, guiding them from day-to-day tactical requests to foundational strategic applications using concrete examples.
• Business Acumen: You have a strong ability to segment customers by their AI comfort levels and use case complexity, identifying which will become force multipliers.
• Startup Adaptability: You thrive in early-stage environments, are comfortable with ambiguity, and enjoy building infrastructure from scratch.
• A Self-Directed Learning Ethic: You believe in building personal mastery first, then teaching what you practice through demonstrated workflows.

If you're passionate about helping senior executives unlock their strategic thinking at scale and want to build customer success infrastructure from the ground up, we'd love to talk with you.