About this role.
Osano is seeking a Customer Success Manager to own a strategic book of Mid Market and Enterprise accounts. This role focuses on driving retention and expansion through data-informed strategies and strong stakeholder relationships. The ideal candidate has 5+ years of SaaS Customer Success experience, proficiency in CRM and AI tools, and a customer-first mindset. As a B-Corp dedicated to privacy, Osano values innovation, accountability, and a responsible approach to AI. This is a dynamic role requiring collaboration across Sales, Product, and Support to ensure long-term customer value.
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4/5Autonomy Level
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Cover letter sample
Dear Hiring Manager,
I am excited to apply for the Customer Success Manager position at Osano. With over 5 years of experience in SaaS Customer Success and Account Management, I have a proven track record of driving retention and measurable expansion in mid-market and enterprise accounts. Your B-Corp mission around privacy and responsible AI deeply resonates with me, and I am eager to contribute to a team that values trust and innovation.
In my previous role, I successfully managed a portfolio of accounts, achieving high GRR and NRR by leveraging data insights and building strong executive relationships. I am highly proficient in HubSpot and AI tools, which allow me to operate efficiently and provide proactive, data-driven guidance to customers. I thrive in fast-paced, ambiguous environments and am committed to creating clarity and value for stakeholders.
I look forward to the opportunity to bring my expertise in customer outcomes, retention strategy, and cross-functional collaboration to Osano. Thank you for your consideration.
Sincerely,
[Your Name]
Sample interview questions
I would start by analyzing product usage data and customer feedback to identify root causes, then proactively schedule a business review with key stakeholders. I would align on their goals and pain points, present a tailored action plan with measurable outcomes, and leverage internal resources (such as Product or Support) to address any issues. I would also set up a regular check-in cadence to monitor health and re-engage champions.
I would focus on value realization first, ensuring the customer is seeing ROI on their current investment. By conducting quarterly business reviews and mapping their objectives to product features, I can identify gaps or new needs that our solutions can fulfill. I would then collaborate with the customer to build a business case for expansion, involving their executives and our Sales team to craft a compelling proposal that aligns with their strategic goals.
I use a tiered prioritization model based on account value, risk, and growth potential. High-risk or high-opportunity accounts get more proactive attention, while lower-touch accounts rely on automated health monitoring and periodic check-ins. I also maintain a clear account plan with milestones and use forecasting tools to stay ahead of issues. This ensures that no account is neglected and that my efforts align with business priorities.
In a previous role, I noticed a customer with low adoption and a pending cancellation. I immediately scheduled a listening session to understand their dissatisfaction, discovered a key integration was missing, and partnered with Product to create a workaround education plan. I also realigned their success criteria and provided dedicated onboarding training. Within two quarters, their usage doubled, they renewed with expansion, and even became a reference for new sales.
I use data analytics tools to monitor health scores, usage trends, and sentiment, allowing me to identify early warning signs and tailor engagement strategies. AI tools like ChatGPT and Claude help me draft personalized communications, summarize customer feedback, and automate routine follow-ups to be more efficient. I am careful to use AI responsibly, always reviewing outputs and ensuring human judgment drives key decisions.
About Osano:
Osano is an innovative B-Corporation built around a simple belief: privacy is a fundamental right. Since day one, we’ve been focused on giving modern enterprises the ability to innovate quickly, stay competitive, and earn customer trust by respecting data privacy and complying with consent guidelines. Our products help organizations operate confidently in a rapidly evolving regulatory and technological landscape.
About the Role:
We’re looking for a Customer Success Manager, Mid Market/Enterprise Accounts to join our Account Management team. This person will play a pivotal role in driving retention, expansion, and long-term customer value across our highest-value accounts.
This position is ideal for someone who is both relationship-driven and data-informed—someone who can build trust with stakeholders while leveraging product insights and metrics to guide strategy and outcomes.
Responsibilities:
Customer Ownership & Retention
- Own and manage a strategic book of business end-to-end, serving as the primary point of contact across executives, business, and technical stakeholders.
- Drive retention with a slight focus on expansion (GRR, NRR, upsell opportunities)
- Monitor customer health, engagement signals, and sentiment to proactively identify and mitigate churn risks
Customer Engagement & Outcomes
- Build strong relationships with key stakeholders that reinforce trust and long-term partnership
- Drive product adoption and measurable customer outcomes
- Partner with customers to define success criteria and guide them through best practices and value realization
Data-Driven Account Management
- Analyze product usage and customer data to inform strategy
- Identify trends, risks, and opportunities across accounts to optimize engagement and outcomes
- Maintain accurate forecasting and account planning, including tracking risks, opportunities, and success metrics.
Cross-Functional Collaboration
- Partner with Sales, Product, and Support to ensure a seamless alignment and aligned customer experience
- Act as the voice of the customer internally, surfacing customer feedback and insights to influence product and process improvements
About You:
- You’re curious, self-directed, and motivated to learn quickly.
- You’re comfortable navigating ambiguity and creating clarity for others.
- You’re excited about privacy, responsible AI, and building trustworthy technology.
- You are willing to relentlessly pursue the best, most responsible ways to leverage AI—without overselling its capabilities or ignoring its limitations.
- You’re highly organized and able to manage multiple accounts and priorities simultaneously
- You’re customer-first and focused on outcomes and value delivery
- You communicate clearly and confidently with stakeholders
- You take ownership and operate with accountability
Must-Haves:
- 5+ years of experience in Customer Success or Account Management within a SaaS environment
- Experience managing a book of business and owning retention and expansion metrics (GRR, NRR, churn)
- Proficiency in CRM systems (preferably HubSpot)
- Strong understanding of SaaS metrics, customer health, and account performance indicators
- Ability to interpret product usage data and customer signals to drive outcomes
- Experience using tools like Gong, Loom, or similar for customer communication and insights
- Strong technical acumen (ability to understand SaaS products, integrations, and workflows)
- Familiarity with AI tools (e.g., ChatGPT, Claude) to improve productivity and communication
Nice-to-Haves:
- Strong interest in AI tools and workflows (prompting, automation, experimentation)
- Experience building automations or workflows using AI tools
- Familiarity with Customer Success platforms (Gainsight, Vitally, or similar)
- Experience with data analysis, reporting, or customer insights tools
- Experience with customer journey mapping or lifecycle design
Why Us:
- We’re a welcoming team that’s dependable, curious, moves fast, and full of talented people
- We’re a B-corporation with a mission that matters, in a high-growth space with significant potential
- You’ll become a privacy expert, including the opportunity to obtain your Certified Information Privacy Manager credential
- You’ll have access to our training program, well-defined career paths, and a leadership team that values professional development
Benefits:
- Competitive-pay compensation and ownership interest/equity
- Unlimited paid time off, plus a requirement to take at least two weeks off per year
- We’re a Best Place for Working Parents and offer paid parental leave for all new parents
- Osano sponsors individual premiums on base plans at 100% and dependent premiums at 50% for Medical, Dental, and Vision insurance via Aetna
- A fully and permanently remote company so you can work from anywhere in the U.S.
- Receive a MacBook and $600 to craft your home workspace
- Annual company trip designed to foster connection, creativity, and fun
- Mental health benefits with free memberships to mindfulness and talk therapy services
A Bit More About Osano
Osano is a leading data privacy platform that helps organizations quickly and confidently comply with laws like GDPR, CCPA, and other global privacy regulations. From consent management to vendor risk monitoring, Osano makes complex privacy tasks refreshingly simple, so companies can focus on what they do best, while we handle the rest.
We’re backed by top-tier investors including Baird Capital, Jump Capital, and LiveOak, and we’re scaling fast with a multi-year runway and ambitious growth plans. We’ve also been recognized as a Great Place to Work for four years running, with 97% of employees saying Osano is a great place to work.
As we grow, we’re looking for individuals who lean into modern technologies and smarter systems to drive efficiency, clarity, and speed; both in our product and in how we operate. If you’re excited by the idea of helping build a high-growth, privacy-first company that embraces thoughtful automation, emerging tech, and intentional collaboration, we’d love to hear from you.
Osano is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, marital status, genetic information, disability, veteran status, or any other characteristic protected by applicable law.
Annual salary information is not provided for this position. Explore salary ranges for similar roles in our Salary Directory ›
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