Digital Customer Success Manager

Who we are:

At Mediafly, we help the world’s top revenue teams work smarter and achieve measurable impact. Our platform brings together sales enablement, content, and performance insights so sellers have the coaching, tools, and intelligence they need to succeed. By weaving value selling into every workflow, we empower teams to accelerate deal cycles, boost win rates, and prove ROI.

For you, that means joining a company where innovation meets purpose—where your work helps businesses deliver more meaningful buyer experiences and drives results that truly matter. You’ll be part of a collaborative, growth-focused team that values expertise, creativity, and human connection.

Mediafly seeks a highly detail-oriented Digital Customer Success Manager to foster customer retention and engagement through innovative, digital-first strategies. With a special emphasis on supporting low ARR accounts, this role centers around using Gainsight CS and PX to execute proactive, personalized customer success programs and scale these approaches across all segments. The successful candidate will actively leverage Gainsight workflows, data, and communications tools and will bring an enthusiasm for marketing or brand ownership to ensure communications deliver impact and consistency. Mediafly values professionals with a keen eye for detail, analytical rigor, and a strong brand sensibility to elevate our customer experience.

• Execute Gainsight-Enabled Customer Engagement: Engage with Mediafly’s customers primarily via Gainsight CS/PX, applying provided workflows, health scoring, and engagement activities for tiered customer segments - focusing on retention and adoption for lower ARR accounts.

• Use Gainsight to trigger precise, thoughtfully branded communications (email campaigns, renewal reminders, onboarding support) based on health scores, product activity, and segment metrics.
• Ensure all engagement activities reflect a high attention to detail, maintaining brand integrity and consistency across touchpoints.

• Deliver Automated, Scalable Digital Programs: Implement and iterate digital-first playbooks and lifecycle touchpoints designed in Gainsight, prioritizing lower ARR customer retention but contributing to programs serving all customer segments.

• Apply marketing best practices to campaign design, messaging, and segmentation, ensuring digital programs support Mediafly’s brand objectives and engagement goals.
• Review engagement outcomes in Gainsight, partnering with cross-functional teams to enhance digital success plans and expand program reach.
• Monitor Customer Health & Drive Adoption: Regularly track customer health and adoption using Gainsight dashboards and reporting tools; analyze engagement trends, feature usage gaps, risk indicators, and opportunities for increased impact.

• Apply data-driven insights to inform program improvements and to optimize communication approaches by segment.

• Collect Feedback & Report Impact: Use Gainsight automation to collect NPS, CSAT, and user feedback at every stage of the customer journey.

• Synthesize and report program outcomes, with a disciplined, detail-oriented approach to metrics interpretation and recommendation presentation.
• Collaborate and Scale Best Practices: Work alongside Product, RevOps, and Customer Success to pilot, adapt, and scale digital engagement strategies for different customer segments.

• Support ongoing education and self-service resource enhancements, contributing a marketing lens to all content intended for retention, onboarding, and customer education.

• Demonstrated detail orientation in managing digital customer success workflows and communications; proven ability to ensure accuracy and consistency across multiple program deliverables.

• 3–5 years hands-on experience with Gainsight CS and/or PX (or similar platforms), including building engagement flows and digital programs.

• Track record in a marketing, brand, or customer communications role, with an understanding of how to create messaging that aligns to brand guidelines and drives engagement.

• Previous experience working on or supporting marketing campaigns is highly preferred.

• Experience in roles focused on customer retention strategy campaigns, including developing and executing programs that drive measurable retention outcomes.

• Proven ability to work cross-functionally with multiple teams to gain alignment and secure buy-in for digital success initiatives.

• Proven success developing, implementing, and scaling data-driven digital customer retention programs, especially for lower ARR segments in SaaS or tech-enabled environments.

• Analytical mindset; demonstrated experience interpreting customer data, program metrics, and behavioral trends to inform decisions and drive measurable outcomes.

• Strong written and verbal communication skills – able to convey results, insights, and recommendations clearly for varied audiences.

• Familiarity with data governance, compliance, and best practices relevant to digital customer engagement.
• Must work east coast standard hours/schedule.

Base Salary Range: $80,000 - $110,000 annually

At Mediafly, we are committed to fostering pay equity and transparency, which are essential to creating a fair and inclusive workplace. We believe that clear and open compensation practices help build trust and ensure that all employees are compensated fairly for their contributions. The specific salary offered for a role will be determined by a variety of factors, including your individual skills, experience, geographic location, and other relevant considerations.

Why Mediafly?

Remote based in US, UK and Canada

Flexible working hours

Generous PTO

Competitive Salary

401K Retirement Plan with match

Transparent Career Paths

Medical, Dental, Vision

Generous Paid Parental Leave

Remote Stipend

Work in a creative environment with high energy

Mediafly is an equal opportunity employer, which means we do not discriminate on the basis of race, color, religion, marital status, age, national origin, ancestry, physical or mental disability, medical condition, pregnancy, genetic information, gender, sexual orientation, gender identity or expression. We celebrate diversity and are committed to creating an inclusive environment for all employees. We welcome people of different backgrounds, experiences, abilities and perspectives and encourage all interested individuals to apply.

Thanks to our commitment to employee experience, Mediafly has been recognized as a Best Place to Work from Crain's, Inc. and BuiltIn.

Mediafly's HQ is based in Chicago, IL.