Customer Success Manager

Inside Real Estate is a fast-growing, independently‑owned real estate software firm that serves as a trusted technology partner to over 500,000 top brokerages, agents, and teams. Their branded portfolio, Bold Trail, includes Bold Trail (Front Office), Bold Trail Back Office and Bold Trail Recruit, solutions that create a complete tech ecosystem for clients, and deliver seamless end‑to‑end operations to scale success at any level.

With an accomplished leadership team and its talented staff, Inside Real Estate brings the resources, scale, and vision to deliver ongoing innovation and success to their growing customer base.

As a Lifetime Customer Success Manager, you will oversee the long‑term success, retention, and growth of existing accounts after their first 30 days. Your role focuses on driving adoption, reducing churn, and ensuring each client continues to see measurable value in the Bold Trail platform. You will partner closely with cross‑functional teams to address escalations, identify upsell opportunities, and maintain strong, ongoing relationships with clients throughout their lifecycle.

• Account Retention:
  Serve as the primary point of contact for all accounts post‑onboarding, focusing on renewal readiness, engagement, and long‑term satisfaction.
• Adoption & Strategy:
  Conduct periodic strategy and adoption calls to ensure clients are using key features and meeting their business goals with Bold Trail.
• Health Monitoring:
  Regularly review account health metrics to identify risk indicators (low adoption, support issues, or inactive users) and proactively intervene.
• Escalation Management:
  Collaborate with Product, Support, and Implementation teams to resolve complex issues, ensuring clients feel supported and informed.
• Growth Opportunities:
  Partner with Account Management to identify expansion or upsell opportunities that align with the client’s goals and usage.
• Customer Advocacy:
  Gather feedback and insights from clients to inform internal teams and help shape future product improvements.
• Collaboration & Handoff:
  Maintain a strong handoff process from Launch CSMs and ensure smooth transitions between lifecycle phases.
• Documentation:
  Accurately log activities, meeting notes, and account health updates in Salesforce for visibility and reporting.

• Experience:
  
  3+ years in Customer Success, Account Management, or a related SaaS role, ideally managing a portfolio of SMB/MM/enterprise clients.
• Skills:
  • Strong relationship‑building and communication skills.
  • Ability to manage a large portfolio while staying organized and proactive.
  • Experience using Salesforce and customer health dashboards.
  • Strategic mindset with a focus on both retention and value realization.
  • Comfort managing escalations and guiding customers toward solutions.

• Competitive salary
• 3 Medical plans to choose from - 1 PPO and 2 HDHPs
• 2 Dental plans to choose from
• Vision
• HSA - company-funded
• FSAs - healthcare, limited purpose, dependent care
• Short‑Term Disability - company‑paid
• Long‑Term Disability - company‑paid
• Basic Employee Life Insurance - company‑paid
• Voluntary Dependent Life Insurance
• Voluntary Accident Insurance
• Voluntary Critical Illness
• Voluntary Hospital Indemnity
• Legal Plan
• Pet Insurance
• 401(k) Retirement Savings with company match
• Paid PTO/Vacation/Sick Time
• 11 company‑recognized holidays
• Company‑paid Parental/Disability Leave

• Opportunities to grow within our company;
• Potential to work in a remote setting;
• Exciting/energetic work environment and fun, creative culture.

IRE EEO Statement - We believe that the unique contributions of all Insiders are the driver of our success. To make sure that our products and culture continue to incorporate everyone's perspectives and experiences we never discriminate on the basis of race, religion, national origin, gender identity or expression, sexual orientation, age, marital, veteran, or disability status.