Customer Success Manager – Scaled, Digital

This is a fully remote position, open to applicants in Illinois, +2 more states.

📋 Description

• Oversee a substantial portfolio of 40–50 mid-market accounts through proactive, data-informed engagement.

• Conduct regular quarterly and/or ad hoc client interactions via digital communications and strategic live meetings.

• Evaluate product usage statistics, NPS feedback, and account health metrics to pinpoint trends, risks, and opportunities.

• Formulate scalable action plans and one-to-many engagement approaches.

• Recognize and cultivate upsell and expansion prospects in collaboration with Sales.

• Represent mid-market client interests internally during product and Customer Success discussions.

• Organize and lead a monthly product webinar that includes updates, best practices, and client Q&A sessions.

• Oversee and enhance the Product University.

• Develop and sustain in-app guidance features, such as tooltips and walkthroughs.

• Document and improve scalable digital engagement playbooks.

• Create proactive post-sale and post-implementation email outreach campaigns.

• Identify portfolio trends that inform product priorities and Customer Success strategies.

• Collaborate with teams in Customer Success, Product, Sales, and Marketing.

• Contribute to internal knowledge resources, client references, success stories, and the advancement of the scaled and digital Customer Success model.

⛳️ Requirements

• Proven experience managing a large volume of accounts (40+), ideally 40–50 at once.

• Capability to establish efficient processes that uphold quality at scale.

• Strong analytical skills to assess customer usage data across various tools.

• Ability to recognize patterns and convert insights into prioritized, actionable outreach strategies.

• Familiarity with digital Customer Success initiatives, webinar facilitation, in-app guidance tools, learning management or product education platforms, and scalable communication methods.

• Confidence in presenting and facilitating webinars for large groups.

• Clear and effective communication skills for written and one-on-one interactions with clients across digital platforms.

• Skill in designing and delivering engaging group training sessions and webinars.

• Outstanding organizational abilities and self-directed time management.

• Capacity to independently prioritize high-impact tasks.

• A genuine commitment to delivering customer value.

• Ability to work collaboratively with teams in Customer Success, Product, Sales, and Marketing.

• Curiosity, resourcefulness, a solutions-oriented perspective, and a willingness to learn continuously.

• Familiarity with commercial real estate technology and property management practices (preferred).

• Must be authorized to work in the United States without sponsorship.

• Visa sponsorship is not available.

🏝️ Benefits

• 401(k) plan with company matching contributions.

• Comprehensive Medical, Dental & Vision Care.

• Paid parental leave at 100% of salary.

• Paid Time Off and company holidays.

• Early access to earned wages through Daily Pay.

• Supportive workplace culture.

• Benefits package that prioritizes mental, physical, and emotional well-being.