Head - Executive/CXO Engagements

San Jose, California, United States | Sales | Full-time

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Who are we?

Founded in 2014 by Khadim Batti and Vara Kumar, Whatfix is a leading global B2B SaaS provider and the largest pure-play enterprise digital adoption platform (DAP). Whatfix empowers companies to maximize the ROI of their digital investments across the application lifecycle, from ideation to training to the deployment of software. Driving user productivity, ensuring process compliance, and improving user experience of internal and customer-facing applications.

Spearheading the category with serial innovation and unmatched customer-centricity, Whatfix is the only DAP innovating beyond the category, positioning itself as a comprehensive suite for GenAI-powered digital adoption, analytics, and application simulation. Whatfix product suite consists of 3 products - DAP, Product Analytics, and Mirror. This product suite helps businesses accelerate ROI on digital investments by streamlining application deployment across its lifecycle.

Whatfix has seven offices across the US, India, UK, Germany, Singapore, and Australia and a presence across 40+ countries.

Customers: 700+ enterprise customers, including over 80 Fortune 500 companies such as Shell, Microsoft, Schneider Electric, and UPS Supply Chain Solutions.

Investors: Raised a total of ~$270 million. Most recently Series E round of $125 Million 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 Investments, Peak XV Partners, and Stellaris Venture Partners.

  • With over 45% YoY sustainable annual recurring revenue (ARR) growth, Whatfix is among the “Top 50 Indian Software Companies” as per G2 Best Software Awards.
  • Recognized as a “Leader” in the digital adoption platforms (DAP) category for the past 4+ years by leading analyst firms like Gartner, Forrester, IDC, and Everest Group.
  • The only vendor recognized as a Customers’ Choice in the 2024 Gartner® Voice of the Customer for Digital Adoption Platforms has once again earned the Customers’ Choice distinction in 2025. We also boast a star rating of 4.6 on G2 Crowd, 4.5 on Gartner Peer Insights, and a high CSAT of 99.8%
  • Highest-Ranking DAP on 2023 Deloitte Technology Fast 500™ North America for Fourth Consecutive Year
  • Won the Silver for Stevie's Employer of the Year 2023 – Computer Software category and also recognized as Great Place to Work 2022-2023
  • Only DAP to be among the top 35% companies worldwide in sustainability excellence with EcoVadis Bronze Medal
  • On the G2 peer review platform, Whatfix has received 77 Leader badges across all market segments, including Small, Medium, and Enterprise, in 2024, among numerous other industry recognitions.

Be one of the key Leaders in this awesome journey of building a billion-dollar company!

About the Role

We are looking to hire a Head - Executive/CXO Engagements - a relationship-first operator whose primary mandate is to unlock C-level access at our most strategic global accounts.

This is not a traditional sales role. There are no direct quotas or transactional expectations - but there will be clear KPIs around account penetration and strategic access (e.g., CXO entry into Top 50 strategic accounts, volume of executive connects, influence on deal velocity, etc.).

Instead, the charter is singular: build and activate executive relationships that accelerate Whatfix’s access, credibility, and influence with Global 2000 CXOs. This role is our go-to connector - turning networks into access and relationships into business velocity.

You will be leveraging investor and board networks, facilitating warm intros, and orchestrating executive-to-executive connects. You’ll serve as a trusted growth partner to Whatfix leadership, customer stakeholders, and investor ecosystems alike.

You must bring a strong existing network of G2K enterprise CXOs and/or have demonstrated experience in building one from scratch - preferably within ISV, SaaS, or enterprise tech ecosystems.

Key Responsibilities

Executive Relationship Development

  • Lead the CXO Connect initiative, engaging C-level leaders (CIOs, CTOs, CDOs, CHROs, CFOs, etc.) across strategic accounts.
  • Orchestrate “No-Agenda” executive interactions between Whatfix leadership (CEO, CRO, etc.) and CXOs - focused on trust-building, not pitching.
  • Design and execute high-touch engagement journeys for target executives across verticals like financial services, healthcare, logistics, and technology.

Investor & Direct CXO Access Activation

  • Leverage the Whatfix investor and board ecosystem to initiate warm introductions to senior enterprise executives.
  • Build a structured playbook to systematically extract executive access via investor relationships—turning network capital into commercial opportunity.
  • Collaborate closely with investors to identify the right CXOs, secure intros, and track downstream influence and impact.
  • Independently cultivate access to CXOs at priority new logos and existing customers—especially across our top 100 strategic accounts—through relationship building, ecosystem influence, and executive credibility.

Strategic Influence

  • Support enterprise sales quotas by influencing deals top-down, unlocking early CXO buy-in and strategic alignment.
  • Work hand-in-hand with account teams to navigate power maps, influence strategy, and guide multithreaded stakeholder engagement.
  • Serve as a trusted partner to founders and AEs, offering CXO-level guidance without overlapping core sales responsibilities.

Ecosystem Connectivity

  • Act as a value-oriented connector, introducing CXOs to relevant peers, innovators, and trusted vendors from the Whatfix network.
  • Facilitate high-value, curated interactions (e.g., innovation briefings, invite-only summits, thought-leadership panels).
  • Position Whatfix as a trusted innovation ally, not just a vendor—by showing up with value and relevance.

Program Building & Measurement

  • Build and scale a repeatable CXO engagement engine, complete with warmth scoring, touchpoint tracking, and influence metrics.
  • Work with tools like Vieu, CTD.ai, and CRM systems to measure relationship depth, frequency, and strategic lift.
  • Track both leading indicators (CXO meetings, net-new intros, warmth scores) and lagging impact (deal velocity, ACV lift, top-down originated deals).

Who You Are

  • A Relationship-Driven Operator: You thrive on human connection and have a proven ability to initiate and sustain deep executive relationships—especially with enterprise CXOs.
  • Enterprise Credible: You carry a strong “business card” with 10+ years of experience in enterprise-facing roles, ideally in SaaS, tech-enabled services, or GTM leadership.
  • Networked via Capital & Credibility: You understand how to activate investor and board networks and you know how to ask for the right intro, at the right time, to the right person.
  • Strategic, Not Transactional: You don’t sell - you influence. You shape deals by enabling trust, credibility, and insight at the highest levels.
  • CXO Fluent: You can hold your own in a room full of CIOs and Chief Digital Officers, and you know what matters to them—from transformation mandates to board priorities.
  • Hands-On & Self-Directed: You’re comfortable operating without a blueprint, and you enjoy building scalable motions from scratch.

Why This Role Matters:

Whatfix is entering a new phase of growth, with a clear path to expand into multi-year, $500K+ and $1M+ deals. But these deals are won through the top, not just the middle. That’s where you come in. You will help shape the future of our GTM motion by turning relationships into pipelines—and CXO access into long-term revenue impact.

Nice to Have

  • Experience at a high-growth, VC-backed SaaS or tech company
  • Prior exposure to field marketing, ABM, or Executive Briefing Center initiatives
  • Background in strategic partnerships, corporate development, or VC ecosystem sales support

To Apply

If you are a connector, a listener, and a trusted operator- ready to help us open doors and change the game- we want to talk to you

Perks / Benefits

  • Unlimited PTO policy
  • Medical, Dental, and Vision coverage
  • 401 K Plan
  • Health savings accounts
  • Restricted stock units
  • Tuition Reimbursement
  • Utility Stipend (internet and phone)
  • Free office Lunches
  • Flexible working hours
  • Employee Assistance Program

Note:

  • 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—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. In any situation that requires additional flexibility, we’re open to considering exceptions on a case-by-case basis to ensure you’re supported in managing both work and life seamlessly.
  • 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;
  • 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