Sr. Customer Success Manager

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.

• 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.

• 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.

• 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.

• 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.

• 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.

• Ability to travel up to once per quarter for customer onsite visits.

• 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

• Self-starter that thrives in fast-paced environments
• Works well with others
• Receptive to change – is flexible. Seeks and adopts improved approaches and processes.
• Initiates action – is results oriented, takes responsibility for actions and outcomes. Meets commitments and strives for high performance.
• Manages the workload - makes timely decisions, prioritizes effectively, solves problems, monitors results and takes remedial action where necessary.
• Technically proficient – able to apply the technical knowledge and skills required in the job role and responsibilities in order to achieve the expected outputs. 
• Takes responsibility for their own learning - knows personal strengths, recognizes development needs, and takes action to improve. Is open to feedback and always seeks to learn. 
• Communicates ideas – respectfully exchange information and proposes a way forward. Listen to views of colleagues and take in diverse perspectives. 
• Works collaboratively – shares knowledge and information, fosters teamwork and contributes to a positive work environment where people want to come to work.  
• Display ethical character and competence - acts with integrity and intent, is accountable for own actions, behaves according to the company values. 

COMPENSATION

This role will receive a competitive base salary + company bonus + variable + benefits. A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed below.

The pay range for this role is $90,000 - $100,000  USD per year.