Head of Customer Success

Job Title:
Head of Customer Success (Maternity Cover)

Contract:
Fixed term (12 months), Full or part-time (3 days a week)

Location:
Remote, with access to London office as required

Reports to:
CEO

About Dragonfly AI:

Founded in 2018, Dragonfly AI is on a mission to revolutionize the branding and retail industry through innovative visual AI solutions. Born from over a decade of research at Queen Mary University of London, our technology helps global industry leaders harness the power of predictive visual analytics. Our platform, grounded in biological principles and enriched with cutting-edge research, is a pioneer in the attention economy, designed to enhance the efficacy and impact of content in today's fast-paced, content-rich environments.

Having recently completed a Series A funding round, Dragonfly AI is entering an exciting phase of growth. With ARR forecast to increase from $2.5m in 2024 to $5m by the end of 2025 and an ambition to reach $20m+ by 2027, now is the perfect time to join our expanding team.

The Role:

We are seeking a full or part-time, fixed-term Head of Customer Success (Maternity Cover) to lead our Customer Success function through an exciting phase of growth at Dragonfly AI, maintaining leadership continuity and operational excellence during a key phase of growth.

Reporting to the CEO, you will inspire and empower a talented Customer Success team, to deliver exceptional value to our global customers driving retention and advocacy across our portfolio, whilst ensuring commercial targets are met. Working closely with Sales, Product, and Marketing, you will ensure Dragonfly AI remains relentlessly customer-centric and commercially aligned.

This is a fixed-term role building on strong GRR and NRR foundations, developing team capability, and helping to shape our customer success strategy. You'll bring strategic clarity, operational excellence, and a passion for customer value to help Dragonfly AI thrive during this pivotal growth period.

Responsibilities:

• Team leadership & development:
• Inspire and coach the Customer Success team (including Principals, Senior CSMs and CSMs) to deliver exceptional results.
• Hold regular 1:1s, development conversations and team meetings focused on performance, learning and collaboration.
• Oversee allocation of customer portfolios and internal resource, ensuring coverage aligns with customer priorities and business goals. Manage CS resourcing for pre-sales support requests
• Customer retention & expansion:
• Own GRR, driving proactive engagement and clear ROI for our customers, identifying potential churn risks and expansion opportunities.
• Partner with Sales to ensure that account teams identify and execute on expansion opportunities across the customer base.
• Operational & strategic continuity:
• Oversee CS initiatives and frameworks (e.g. onboarding, QBRs, success planning), ensuring consistency of delivery and continuous improvement.
• Have ownership of relevant tooling and systems such as HubSPot and Planhat.
• Empower Principal CSMs to lead defined strategic projects, ensuring accountability and alignment with company goals.
• Cross-functional leadership:
• Represent Customer Success in leadership and cross-functional forums, shaping decisions that strengthen Dragonfly's market position
• Ensure the voice of the customer continues to influence product roadmap, commercial decisions and customer engagement strategies.
• Executive sponsorship:
• Act as executive sponsor for select accounts, building trusted relationships at senior levels and ensuring long-term partnership success.
• Lead from the front for at-risk accounts, providing hands-on support to retain and protect revenue.
• Reporting & insight:
• Maintain regular reporting on customer health, churn risk, renewals pipeline, and overall team performance for the CEO and Leadership Team.

Experience:

• 10+ years in Customer Success with a proven record of managing and growing enterprise accounts.
• Strong leadership background, ideally having led and scaled teams within a SaaS environment.
• Deep understanding of retention, expansion, and customer advocacy levers.
• Skilled in cross-functional collaboration, influencing across Product, Sales, and Marketing.
• Confident presenting customer outcomes and insights at senior/executive level.
• An empathetic, collaborative leader who inspires trust quickly, upholds high standards, and brings clarity and focus to the team during a period of transition.

Employment Terms:

• Competitive salary and benefits package.
• Opportunities for remote work with required periodic travel to our London office and client sites, including occasional travel to the United States.

Why Work for Dragonfly AI?

At Dragonfly AI, you'll join a rapidly growing company that values innovation and creativity. We offer unlimited holiday and trust our staff to manage their own schedules, ensuring a healthy work-life balance. Our rapid commercial growth not only signals our success but also forecasts the expansion of our teams, providing numerous opportunities for career advancement and leadership roles. Our environment encourages new ideas and supports your growth through continuous learning and leadership opportunities. Working with us means being at the forefront of cutting-edge technology, in a company that truly values its people first.