Senior Customer Success Manager, UpKeep

• Bachelor's Degree a plus in business, communications, or similar field
• 2+ years experience in a customer-facing customer success or account management role
• Experience with Salesforce
• Experience with being measured by Gross Revenue Retention, Net Revenue Retention, or similar metrics
• Experience with a previous cloud-based or SaaS company
• Ability to honor deadlines and follow through on commitments
• Outstanding prioritiztaion, organization, and time management skills
• Strong written and verbal communication skills. Ability to manage multiple streams of communication
• Strong web presentation skills
• Basic technical aptitude to understand how to troubleshoot issues and provide effective solutions
• Possess ability to diagnose non-technical issues and prescribe next steps
• Possess ability to set clear expectations with customers
• Possess ability to be assertive but empathetic during customer interactions
• Skillful at managing relationships
• Possess basic business acumen to understand how business principles relate to customer success
• Works collaboratively – shares knowledge and information, fosters teamwork and contributes to a positive work environment where people want to come to work

Desirable

• As a Sr. Customer Success Manager (Sr. CSM), you will be responsible for a portfolio of accounts within our “high touch” engagement model
• Your core focus will be to drive product adoption, maximize customer value, and to perform proactive activities to mitigate churn risks as well as uncover expansion opportunities
• You will serve as the primary advocate for the customer and work with cross-functional teams to deliver an exceptional customer experience
• Success in this role will be measured by key metrics such as revenue retention, revenue expansion, customer engagement, and account adoption outcomes
• Customer Ownership & Engagement:
• Manage a dedicated book of business within a high-touch engagement model, serving as the primary point of accountability for customer success
• Build strong, trusted customer relationships through recurring weekly or monthly meetings, ongoing email and phone communication, and periodic onsite engagements
• Multi-thread engagements within high-ARR accounts by identifying, engaging, and sustaining relationships with multiple stakeholders—including champions, administrators, and executive sponsors—to ensure continuity, alignment, and long-term partnership
• Act as a trusted product advisor, driving sustained usage and adoption of UpKeep’s core platform and all add-on products to maximize long-term customer value
• Share best practices related to user adoption, system administration, and maintenance workflow optimization to help customers achieve their desired business outcomes
• Deliver value-driven engagements such as adoption check-ins, quarterly business reviews (QBRs), and tailored product walkthroughs
• Drive consistent customer engagement across multiple channels, including email, phone, video conferencing, webinars, and onsite visits as needed
• Conduct proactive outreach to non-engaged or at-risk accounts to assess customer needs, satisfaction, and overall partnership health
• Complete a defined number of customer touchpoints each week (e.g., phone calls placed and meetings hosted) to maintain momentum and visibility across accounts
• AI-Enabled Execution:
• Leverage AI daily to prepare for meetings, execute engagements, summarize outcomes, and deliver timely follow-ups
• Use AI to reduce manual effort, improve efficiency, and drive consistency across the customer lifecycle
• Promote and support adoption of UpKeep’s AI capabilities by guiding customers in transforming manual workflows with UpKeep Intelligence and related AI solutions
• Revenue Retention:
• Proactively monitor account health scores, usage trends, and risk indicators to identify and mitigate churn or downgrade risks
• Rally internal executives and senior stakeholders for key renewal discussions and high-risk customer situations to reinforce partnership value and executive alignment
• Partner closely with the Retention Team to resolve churn and downgrade requests and reinforce long-term customer value
• Revenue Expansion & Renewals:
• Identify expansion opportunities through proactive discovery and make strategic recommendations for plan upgrades, additional users, or additional products
• Collaborate with the Sales team to support renewal confirmations and expansion motions, particularly within high-ARR accounts
• Cross-Functional Collaboration & Process Improvement:
• Partner with Technical Support, Professional Services, Sales, and Product teams to address customer needs and deliver a seamless, high-quality customer experience
• Contribute to the continuous improvement of internal processes, playbooks, and standard operating procedures