Outbound In-Life Retention Representative

Mon, 01/26/2026 - 06:02

The Outbound In-Life Retention Representative is responsible for proactively engaging Sage 50 customers during their contract lifecycle ("in-life") to maximize retention, minimize churn, and drive upsell opportunities. This role focuses on strategic outreach to renewal accounts, identifying risks, and delivering solutions that encourage customers to remain with Sage.
Key Responsibilities

Proactive Customer Outreach

• Initiate outbound calls to assigned renewal accounts and customers identified as at risk of churn.

• Prioritize outreach based on churn risk, contract expiration, and customer value.

• Build relationships with customers throughout their lifecycle to encourage renewal and satisfaction.

Retention & Save Motion

• Conduct needs assessments to understand customer concerns and reasons for potential cancellation.

• Present tailored solutions, offers, or add-on modules that address customer needs and increase value.

• Handle objections empathetically and work to resolve issues that may lead to churn.

Upsell & Cross-Sell

• Identify and pursue upsell and cross-sell opportunities during retention conversations.

• Educate customers on additional Sage 50 products, modules, and services that can enhance their experience and business outcomes.

Account Management

• Maintain accurate and up-to-date customer records in Salesforce CRM.

• Document all interactions, outcomes, and agreed-upon actions immediately after each call.

• Schedule and conduct follow-up calls as needed to ensure customer satisfaction and resolution.

Collaboration & Continuous Improvement

• Work closely with internal teams (marketing, sales, customer success) to share insights and improve retention strategies.

• Participate in regular team meetings to review performance metrics, share best practices, and contribute feedback for product and service enhancements.

Reporting & Performance Management

• Track and report daily call outcomes, retention rates, and reasons for unsuccessful retention attempts.

• Meet or exceed defined KPIs, including retention rate, upsell volume, and customer satisfaction scores.

Qualifications

• 1+ year experience in B2B sales, account management, or retention roles within SaaS or technology sectors.

• Proven ability to manage retention and upsell conversations with decision-makers.

• Strong communication skills (verbal and written), active listening, and objection handling.

• Experience using Salesforce CRM for pipeline management and documentation.

• Ability to work independently in a fast-paced, high-volume environment.

• Strong organizational skills, including prioritization and time management.

Perks? We have plenty.

• Competitive salaries that landed us in the top 5% of similar-sized companies (according to Comparably).

• Comprehensive health, dental, and vision coverage.

• 401(k) retirement match (100% matching up to 4%).

• 32 days paid time off (21 personal days, 10 national holidays, 1 floating holiday).

• 18 weeks of paid parental leave for birth, adoption, or surrogacy offered 1 year after the start date.

• 5 days paid yearly to volunteer (through Sage Foundation).

• $5,250 tuition reimbursement per calendar year starting 6 months after the hire date.

• Sage Wellness Rewards Program ($600 wellness credit and $360 fitness reimbursement annually).

• Library of on-demand career development options and ongoing training offerings.

What it’s like to work at Sage:

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