Head of Revenue Retention

Flosum is a fast-growing Salesforce DevOps, data backup, and security SaaS company, and we are seeking an experienced Head of Retention to lead our efforts in revenue retention across all customer segments. In this senior role, you will be 100% focused on retaining and expanding revenue from existing customers – not on new customer acquisition – by driving strategies to minimize churn and maximize customer lifetime value. Reporting to senior leadership (e.g. VP of Sales or CRO), you will own the renewal process and gross/net retention metrics, ensuring that our customers remain satisfied, loyal, and continue to derive value from our platform. This role is highly sales-oriented and strategic, requiring a combination of hands-on account management, data-driven planning, and cross-functional collaboration to turn churn risks into renewal successes. You will also manage and mentor a dedicated retention team, setting the vision and direction for all retention initiatives.

• Retention Strategy & Execution: Develop and implement a comprehensive customer retention strategy and playbook, aligning with Flosum’s business goals. This includes designing initiatives to reduce churn, improve renewal rates, and drive upsell opportunities within the existing customer base. You will own the end-to-end renewals process, from early renewal engagement through contract negotiation and closure, to achieve or exceed gross and net revenue retention targets.
  
• Team Leadership & Coaching: Manage the day-to-day operations of the retention team, serving as the direct line manager for retention specialists/account managers.  Provide strong leadership through hiring, coaching, and motivating team members to hit their KPIs and develop professionally. Join customer calls or meetings as needed to support the team, offer feedback, and coach on messaging, objection handling, and relationship management techniques. Foster a high-performance, customer-centric culture within the team.
  
• Renewal Pipeline Management: Oversee the renewals pipeline across all customer segments (SMB, mid-market, enterprise), ensuring timely and proactive engagement with each customer well before contract expiration. Map and distribute renewal targets, manage forecasting of renewals, and track weekly activity metrics (calls, meetings, QBRs) to ensure the team is on pace. Identify any revenue at risk and formulate action plans to address it promptly. Maintain an accurate forecast of upcoming renewals and report on retention outlook to executives.
  
• Customer Relationship Management: Partner closely with Customer Success Managers and Support teams to monitor customer health scores, product usage, and satisfaction indicators. Identify at-risk accounts through data (e.g. declining usage, support issues, NPS feedback) and work with the team to execute win-back or save plans. Personally engage with strategic high-value customers, including leading executive business reviews or renewal negotiations for key accounts, to reinforce value, address concerns, and secure long-term commitments.
  
• Cross-Functional Collaboration: Collaborate with other departments to ensure a holistic approach to customer retention. Work with Product on addressing feature gaps or performance issues that could impact renewals, conveying customer feedback and advocating for improvements. Coordinate with Marketing on targeted customer communications, loyalty programs, and value-add campaigns that drive engagement and adoption. Align with the New Business Sales team and Account Executives to share insights and best practices – for example, ensuring a smooth handoff from sales to post-sales, and leveraging upsell/cross-sell opportunities without losing focus on the customer’s success.
  
• Retention Initiatives & Continuous Improvement: Design and execute initiatives such as early renewal incentives, onboarding improvements, customer training webinars, and loyalty or advocacy programs to increase customer stickiness. Continuously develop and refine retention processes and playbooks to improve predictability and efficiency of renewals. Stay informed on industry best practices and competitor activities in the Salesforce ecosystem, bringing new ideas to improve our retention approach.
  
• Contract Negotiation & Administration: Take ownership of the commercial aspects of renewals. Negotiate renewal contracts (pricing, term adjustments, upsell packages) in line with company guidelines, ensuring mutually beneficial outcomes for the customer and Flosum. Work closely with Revenue Operations and Legal as needed to handle contract terms, procurement processes, or compliance requirements for enterprise accounts. Ensure all renewals are closed on time or ahead of time, with proper documentation and minimal revenue leakage.
  

Metrics, Reporting & Accountability: Track and analyze key retention metrics, including Gross Renewal Rate, Net Revenue Retention (NRR), churn rate, contraction/expansion revenue, and customer satisfaction scores. Be accountable for achieving retention KPI targets and regularly report on performance to the executive team. Provide weekly or monthly retention reports and forecasts, highlighting results, risks, and planned mitigation for any at-risk accounts. Use a data-driven approach to make decisions and to demonstrate the ROI of retention programs (for example, showing how proactive outreach or a training initiative improved renewal rates).

• Proven Experience in B2B SaaS Retention: 8+ years of experience in account management, customer success, or sales roles with a focus on existing customer revenue growth and retention. You should have a track record of delivering or exceeding revenue retention targets (renewal rates, NRR) in a subscription-based business.Experience in the Salesforce ecosystem or related enterprise software is highly desirable.
  
• Leadership & Team Building: Demonstrated ability to build, lead, and scale a high-performing team.You have prior experience managing account managers or renewal specialists, including hiring talent and developing them. Strong leadership presence with the ability to inspire your team, set clear goals, and foster accountability.
  
• Sales and Negotiation Skills: Exceptional communication and negotiation skills to engage C-level stakeholders and procurement teams during renewal discussions.  Adept at consultative sales techniques, handling objections, and finding win-win solutions to secure renewals and upsells. A customer-centric mindset is a must – you excel at building relationships and trust over long B2B sales cycles.
  
• Strategic & Analytical Thinking: Data-driven decision maker with sharp analytical skills.Proficient in leveraging CRM systems (e.g., Salesforce) and customer success tools (health scoring, analytics dashboards) to identify trends and drive actions. Able to dissect churn data or usage metrics to pinpoint root causes and adjust strategy accordingly. Experience with forecasting and pipeline management for renewals is required.
  
• Cross-Functional Collaboration: Comfortable working cross-functionally and influencing without direct authority. You have worked closely with Customer Success, Product, Marketing, and Sales teams to align efforts in keeping customers successful and happy. Ability to translate customer feedback into actionable insights for other departments is important.
  
• Knowledge of Customer Lifecycle: Deep understanding of the customer lifecycle and churn prevention strategies – from onboarding, adoption, and value realization, to renewal, expansion, and advocacy. Familiarity with best practices in customer success management, such as health scoring, QBRs (Quarterly Business Reviews), and customer advocacy programs.
  
• Industry Background: B2B SaaS experience is required, preferably in enterprise software or cloud services. Experience in the Salesforce ecosystem (e.g. Salesforce AppExchange partners, DevOps/Backup tools, or related domains) is a strong plus, as it provides valuable context for our product and customer needs.
  

Education: Bachelor’s degree in business, marketing, or related field is preferred. Relevant advanced training or certifications (e.g. Salesforce certifications, Customer Success management courses) can be an advantage.

Join Us at Flosum 

Become an integral part of an environment that empowers excellence, irrespective of your location. As a globally distributed company, we champion equal opportunity and nurture a culture of collaboration. Embark on a journey of growth and innovation by applying now. 

Competitive Compensation Package

Health Benefits including Vision and Dental

HSA & FSA

401(k)

Unlimited Flex Time Off Plan + All Major U.S. holidays

Flexible Work Hours

Remote Work Location

Phone / Internet Monthly Capped Reimbursement