Head of Customer Success Operations & Strategy | 261026

<h2 dir="ltr">Who are we?&nbsp;</h2><p dir="ltr">Whatfix is an AI platform advancing the &ldquo;userization&rdquo; of enterprise applications, empowering companies to maximize the ROI of their digital investments. Technology needs adoption. It&rsquo;s no different for AI. As AI reshapes roles, workflows, and human-machine interactions, it also introduces new layers of complexity and user friction. This is where Whatfix plays a pivotal role. A decade old&nbsp; DNA of empowering people to succeed with technology and not replacing them. We call this philosophy Userization: the belief that technology must adapt to the user, not the other way around.&nbsp;</p><p dir="ltr">At the heart of userization philosophy is ScreenSense, our proprietary AI engine, which continuously interprets both the context of what users are doing in an application or an AI tool and the intent behind their actions. By combining these signals, Whatfix delivers real-time guidance, nudges, knowledge, and automation directly in the flow of work.</p><p dir="ltr">This intelligence powers our entire product suite.&nbsp;</p><ul><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Digital Adoption helps users get productive faster.&nbsp;</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Product Analytics uncovers friction and closes adoption gaps.&nbsp;</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Mirror allows employees to train in safe, simulated environments.</p></li></ul><p dir="ltr">&nbsp;These are embedded with Whatfix AI Agents which supercharge creation, insights, and user guidance.</p><p dir="ltr">Our upcoming AI-first products are already creating a buzz in the market.&nbsp;</p><ul><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Seek is an AI-native assistant that not only knows your business context but can also act across applications to get work done on your behalf.&nbsp;</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Whatfix Mirror 2.0 is the world&rsquo;s only System plus Role simulation with a complete assessment to lead the Gen AI simulation category.</p></li></ul><p dir="ltr">Together, these products reflect Whatfix&rsquo;s commitment to building enterprise-ready AI teammates that maximize productivity and ROI. It gives users a unified, intelligent way to find answers across systems, apps, and knowledge silos and helps anyone looking to deliver fast and contextual answers.&nbsp;</p><p dir="ltr">Whatfix is bridging the gap between rapid technological change and human enablement&mdash;ensuring AI is not only embedded but also usable, trusted, and outcome-driven for every employee.&nbsp;</p><p dir="ltr">At Whatfix, we&rsquo;re not just making software easier&mdash;we&rsquo;re making AI work for people.</p><p dir="ltr">The company has seven offices across the US, India, UK, Germany, Singapore, and Australia and a presence across 40+ countries.</p><p dir="ltr">Customers: 700+ enterprise customers, including 80+ Fortune 500 companies such as Shell, Schneider Electric, and UPS Supply Chain Solutions.&nbsp;</p><p dir="ltr">Investors: A total of ~$270 million USD has been raised as yet. Most recently Series E round of $125 Million USD led by Warburg Pincus, with participation from existing investor SoftBank Vision Fund 2. Other investors include Cisco Investments, Eight Roads Ventures (A division of Fidelity Investments), Dragoneer, Peak XV Partners, and Stellaris Venture Partners.</p><p dir="ltr">Whatfix&rsquo;s leadership is consistently recognized across top industry analysts and business rankings:</p><ul><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Won the 2025 <a href="https://aibreakthroughawards.com/2025-winners/">AI Breakthrough Award</a> for the Overall AI-based Analytics Solution of the Year&nbsp;</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Only DAP to be recognized as a &ldquo;Leader&rdquo; across various DAP reports for the past 5+ years by leading analyst firms like Gartner, Forrester, IDC, and Everest Group.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">With over 45% YoY sustainable annual recurring revenue (ARR) growth, Whatfix is among the &ldquo;Top 50 Indian Software Companies&rdquo; as per G2 Best Software Awards.&nbsp;</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">&nbsp;Named a Gartner Customers&rsquo; Choice for DAP for the second year in a row (2024 and 2025)&mdash;the only vendor in the market to earn this distinction consecutively.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">We also boast a star rating of 4.6 on G2 Crowd, 4.5 on Gartner Peer Insights, and a super-high CSAT of 99.8%</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation"><a href="https://stevieawards.com/sales/2025-stevie-award-winners">Stevie</a> Award winner in the category (Bronze): Customer Service Department of the Year &ndash; Computer Software - 100 or More Employees.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Winner of the <a href="https://whatfix.com/newsroom/press-releases/whatfix-and-sophos-win-innovation-award-at-the-2024-isg-paragon-awards-emea/">ISG Paragon </a>Innovation Award in partnership with Sophos (customer) for the EMEA region and finalist in the Transformation Award category.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation"><a href="https://remotetechbreakthrough.com/2024-winners/">RemoteTech Breakthrough Awards</a> winner for &ldquo;Software Asset Management Solution of the Year&rdquo;</p></li></ul><p><strong>&nbsp;</strong></p><p dir="ltr">These recognitions are matched by business performance:&nbsp;</p><ul><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Highest-Ranking DAP on 2023 Deloitte Technology Fast 500&trade; North America for Fifth Consecutive Year</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Listed on the Financial Times &amp; Statista's High-Growth Companies Asia-Pacific 2025 list.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Won the Silver for Stevie's Employer of the Year 2023 &ndash; Computer Software category and also recognized as Great Place to Work 2022-2023&nbsp;</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Only DAP to be among the top 35% companies worldwide in sustainability excellence with EcoVadis Bronze Medal</p></li></ul><p dir="ltr"><em><strong>Be one of the key Leaders in this awesome journey of building a billion-dollar company!</strong></em></p><p dir="ltr">&nbsp;</p><p dir="ltr"><strong>About the role:</strong></p><p dir="ltr">Whatfix is looking for a strategic, data-driven leader to build and run the operating system behind our Customer Success organisation. As Head of CS Operations &amp; Strategy, you will own the frameworks, tools, processes, and intelligence that enable our CS teams to drive measurable customer outcomes at scale.</p><p dir="ltr">Reporting directly to senior CS leadership, you will sit at the intersection of strategy, analytics, and execution, translating business goals into operational playbooks, and surfacing insights that shape how we grow and retain our enterprise customer base globally.</p><p dir="ltr">&nbsp;</p><p dir="ltr"><strong>Key Responsibilities:&nbsp;</strong></p><ul><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Design and own the CS operating model &mdash; including coverage design, segmentation strategy, capacity planning, and headcount modelling across onboarding, adoption, and renewal motions.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Build and maintain the CS analytics practice: dashboards, health scoring, churn prediction models, and expansion signals that give CS leaders real-time visibility into portfolio health.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Own the CS tech stack (CRM, BI tools), driving adoption, governance, and continuous improvement across the tooling layer.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Lead quarterly and annual CS planning cycles, working cross-functionally with Finance, Sales, and Product to align on ARR targets, retention goals, and resource allocation.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Define and operationalise customer journey playbooks , from onboarding through renewal and expansion,&nbsp; ensuring consistency across regions and segments.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Partner with RevOps and Sales Ops to ensure seamless hand-offs, unified data definitions, and a single source of truth across the customer lifecycle.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Drive strategic initiatives such as digital CS motions, scaled customer programmes, and the integration of AI-assisted workflows into the CS delivery model.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Act as a trusted thought partner to CS leadership on organisational design, performance management, and go-to-market strategy.</p></li></ul><p dir="ltr">&nbsp;</p><p dir="ltr">Qualification Criteria:&nbsp;</p><ul><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">10+ years of experience in CS Operations, Revenue Operations, or Strategy roles within B2B SaaS.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Proven track record of building CS operational infrastructure from the ground up or significantly scaling an existing function.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Deep expertise in Salesforce, and BI tools (Tableau, Looker, or similar) and Excel (or Gsheets)</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Strong analytical and financial modelling skills; comfortable building business cases and presenting to executive leadership.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Experience working with enterprise-segment customers and understanding of complex, multi-stakeholder sales and success cycles.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Excellent cross-functional communication and stakeholder management skills.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Prior experience managing or mentoring a team is strongly preferred.</p></li></ul><p><strong>&nbsp;</strong></p><p dir="ltr"><strong>You will stand out if:</strong></p><ul><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">You have worked in a Digital Adoption Platform or adjacent category (LMS, ITSM, CRM implementation).</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">You have led a CS Ops function through a hypergrowth phase or a pre-IPO/liquidity event.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">You have built AI-assisted CS workflows or automated customer health triggers at scale.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">You have experience with global CS operations spanning North America, EMEA, and APAC.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">You are comfortable with ambiguity and have strong instincts for prioritisation in a fast-moving environment.</p></li></ul><p dir="ltr">&nbsp;</p><p dir="ltr">Perks &amp; Benefits (India):</p><ul><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Best-in-class medical insurance coverage</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Free lunch &amp; dinner buffet&nbsp;</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Doorstep cab drop facility&nbsp;</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Education sponsorship&nbsp;</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Internal job transfer &amp; global mobility programs&nbsp;</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">Scope to represent Whatfix at global events</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">We also provide uncapped incentives, bonus plans and opportunities to employees (especially those in GTM teams) to travel to meet our global customers</p></li></ul><p dir="ltr">Note:&nbsp;</p><ul><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">We strive to live and breathe our Cultural Principles and encourage employees to demonstrate some of these core values - Customer First; Empathy; Transparency; Fail Fast and scale Fast; No Hierarchies for Communication; Deep Dive and innovate; Trust, Do it as you own it;&nbsp;</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">We are an equal opportunity employer and value diverse people because of and not in spite of the differences. We do not discriminate on the basis of race, religion, color, national origin, ethnicity, gender, sexual orientation, age, marital status, veteran status, or disability status&nbsp;</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">At Whatfix, we deeply value collaboration, innovation, and human connection. We believe that being together in the office five days a week fosters open communication, strengthens our sense of community, and accelerates innovation&mdash;ultimately helping us achieve our goals more effectively. At the same time, we recognize the importance of flexibility in balancing personal and professional priorities. To support this, we offer the option to work from home up to two days per month.</p></li><li dir="ltr" aria-level="1"><p dir="ltr" role="presentation">In any situation that requires additional flexibility, we&rsquo;re open to considering exceptions on a case-by-case basis to ensure you&rsquo;re supported in managing both work and life seamlessly.</p></li></ul>