Customer Success Lead at Olivai

About Us Oliv.AI is a SalesTech global startup headquartered in San Francisco, debuting the world's first team of AI Agents for sales. With our recent $5.2M Seed funding, we solve one of the biggest problems for revenue teams: unreliable deal data. Oliv captures Deal Intelligence from every meeting, call, and email—without any rep involvement. The result is a clear, detailed view of every deal, presented in scorecards built on trusted sales methodologies like MEDDICC, BANT, and SPICED. Our AI agents are built for sales teams—sales managers, AEs, and RevOps—handling the work that takes them away from selling. With Oliv AI, sales teams can bring back focus on deals, strategy and conversation. Customer Success Manager / Enterprise Onboarding We’re hiring a Customer Success Manager / Enterprise Onboarding to own some of the most important parts of the customer journey: trial, onboarding, implementation, and early adoption. This is not a conventional customer success role. We are not looking for someone who simply manages follow-ups, coordinates support queries, or operates as a reactive post-sales layer. We are looking for someone with high agency, strong judgment, exceptional organization, and real problem-solving ability someone who can understand a customer’s problem in depth, think structurally about how to solve it, and drive execution end-to-end. As we increasingly work with mid-market and enterprise customers, the quality of onboarding and trial orchestration becomes a strategic lever. We need someone who can engage with maturity, bring clarity to ambiguity, run a tight process, and build confidence with customers from the very first interaction. This role sits at the intersection of customer success, project management, and product thinking. It is ideal for someone who enjoys owning outcomes, navigating complexity, and acting as a trusted bridge between the customer and internal teams. What you’ll do • Own customer trials, onboarding, implementation, and early adoption end-to-end • Act as the primary point of contact for customers during the trial and onboarding journey • Understand customer pain points, workflows, and priorities, and translate them into a clear execution plan • Run weekly check-ins, stakeholder reviews, and progress conversations with customers • Coordinate closely with internal teams across sales, product, and implementation to ensure momentum and alignment • Drive structure across milestones, risks, blockers, dependencies, and next steps • Think beyond execution and help shape the right solution for the customer using strong product and business judgment • Guide customers toward successful adoption by aligning product capabilities with their real-world use cases • Surface customer feedback, implementation learnings, and product gaps back into the organization • Ensure a smooth transition from evaluation to onboarding to adoption • Over time, potentially manage or mentor a junior PM / CSM supporting execution What we’re looking for • 3-5 years of experience across customer success, implementation, product operations, solutions consulting, management consulting, or related SaaS roles • Strong project management and stakeholder management ability • Excellent problem-solving skills and structured thinking • A genuine product mindset, able to understand a business problem and think through how the product can solve it • Strong communication skills and the maturity to work with demanding mid-market and enterprise stakeholders • High ownership, exceptional organization, and attention to detail • Comfort with ambiguity, pace, and evolving processes • The ability to operate independently, exercise sound judgment, and create clarity where none exists Ideal background We are particularly interested in candidates who bring a combination of intellectual sharpness, execution discipline, and customer-facing maturity. Relevant backgrounds may include: • High-growth SaaS roles in customer success, implementation, solutions, or product-adjacent functions • Top-tier consulting experience, especially with 1–3 years in management consulting and strong operating instinct • Strong academic pedigree such as IIM, ISB, IIT, top undergraduate institutions, or equivalent • Candidates who may not come from these exact backgrounds but clearly demonstrate high cognitive ability, strong judgment, and a product-first approach What makes this role different Most customer success roles in SaaS are designed around support, coordination, or account coverage. This one is different. We are hiring for someone who can think, not just manage tasks. Someone who can listen to a customer, understand the underlying problem, impose structure on the situation, and drive the right outcome with credibility and ownership. This role requires someone who is not only organized and customer-oriented, but also analytical, mature, and commercially aware. In many ways, this person will operate less like a traditional CSM and more like a customer-facing operator with product and execution depth. Why join us You’ll work closely with the founding team on a function that is becoming increasingly strategic as we scale into larger accounts. This role offers the opportunity to shape how customers experience the product from day one, influence internal execution, and build a high-trust function with significant ownership. We want to make sure everyone has an equal chance to participate and make a difference. Oliv.AI is an equal opportunity employer and prioritizes building a diverse and inclusive workplace. We provide equal employment opportunities to all employees and applicants of any type and do not discriminate based on race, color, religion, national origin, gender, age, sexual orientation, physical or mental disability, genetic information or characteristic, gender identity and expression, veteran status, or other non-job related characteristics or other prohibited grounds specified in applicable federal, state, and local laws. Oliv’s policy is to comply with all applicable laws related to nondiscrimination and equal opportunity and will not tolerate discrimination or harassment based on any of these characteristics. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.