Job Description

Are you a proactive, customer-focused professional who thrives on building relationships and delivering exceptional client experiences?

Do you enjoy solving problems, optimizing retention strategies, and helping customers maximize the value of their subscriptions? Are you eager to work in a fast-paced, AI-driven environment and help non-profits embrace cutting-edge technology? If so, Sidecar is looking for you!

About Sidecar

Sidecar is a dynamic digital media and education platform within the Blue Cypress family of companies. We empower association leaders to innovate and thrive in a rapidly changing technological landscape. Sidecar is at the forefront of AI education and digital transformation, offering resources like our AI Learning Hub, industry-leading podcast, Sidecar Sync , and our flagship conference, digitalNow , which brings Silicon Valley-level insights to the non-profit sector.

As part of Blue Cypress, Sidecar is dedicated to maximizing social sector impact through innovation, providing cutting-edge educational resources and driving change within associations. We are committed to helping associations harness the power of AI and other advanced technologies to stay ahead of the curve.

Job Summary:

The Client Success Manager plays a pivotal role in maximizing customer engagement, satisfaction, and retention across Sidecar’s AI Learning Hub, including Teams memberships, individual memberships, and association partnerships. This role ensures that both organizations and individuals fully utilize the value of their Sidecar subscriptions and that we continually improve client experiences.

This is not a reactive support role—the Client Success Manager will also take a proactive, high-touch approach, helping customers succeed through strategic engagement, onboarding, and ongoing education.

Your primary responsibilities will include:

· Customer Engagement & Retention: Develop and execute strategies to increase retention rates for both AI Learning Hub individual users and enterprise (Teams) clients.

· Proactive Support: Regularly check in with clients to ensure they are maximizing the benefits of their Sidecar membership, providing recommendations and resources tailored to their needs.

· White-Glove Onboarding: Manage onboarding experiences for new AI Learning Hub members, ensuring they understand how to leverage Sidecar’s offerings.

· Renewal & Expansion Strategy: Identify opportunities to upsell or expand existing client relationships, particularly moving individual users toward Teams-level subscriptions or Learning Hub for Members partnerships.

· Client Problem-Solving: Work with customers to address challenges, resolve issues, and optimize their experience using Sidecar’s AI-powered learning solutions.

· Collaboration with Sales & Marketing: Partner with the Manager of Sales and Partnerships and CMO to refine messaging, identify client needs, and develop outreach strategies that drive adoption and engagement.

· Industry & Product Knowledge: Develop expertise in AI Learning Hub offerings and AI applications in the association space to provide knowledgeable support and guidance.

What We’re Looking For:

• 3+ years of experience in client success, account management, or customer support, preferably in SaaS, education, or professional services.
• Experience in leveraging AI-driven tools and strategies.
• Experience with subscription-based services or membership organizations is highly preferred.
• A proactive mindset—someone who doesn’t wait for clients to reach out but instead takes the initiative to ensure engagement and retention.
• Strong problem-solving and relationship-building skills to support clients at every stage of their journey.
• Comfort interacting with association leadership and other senior decision-makers.
• Excellent communication skills and the ability to present solutions confidently.
• Highly adaptable, self-motivated, and comfortable executing in a fast-paced, small-team environment.

Why Sidecar?

This role offers the opportunity to accelerate your career in a leadership role while being mentored by industry experts. You will play a critical part in shaping the marketing and sales strategies of a company at the cutting edge of AI education for associations. You’ll benefit from:

• A supportive team: We provide mentorship and coaching to help you achieve your full potential.
• Cutting-edge technology: You’ll be at the forefront of AI adoption, helping to shape the future of the nonprofit sector.
• Opportunities for growth: As Sidecar grows, so will your opportunities within our company and the broader Blue Cypress ecosystem.
• A meaningful mission: Your work will directly contribute to helping associations and nonprofits thrive in an era of rapid technological change.
• Benefits/perks: Medical, dental, and vision insurance; 401(k); Flexible PTO; Professional development opportunities; Advancement opportunities.

We are committed to fostering an inclusive workplace and welcome individuals from diverse backgrounds to apply. If you're passionate about building community and leveraging technology to drive meaningful change in the nonprofit sector, we would love to hear from you!

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