Enterprise Account Executive

Whatfix; San Jose (CA); On-site; USD 250,000 - 280,000; Full time

Benefits offered by this job

Unlimited PTO

Paid maternity leave

Health insurance (medical, dental, on)

HSA stipend

Relocation sponsorship

Job summary

Whatfix is actively seeking an Enterprise Account Executive to sell to Fortune 500 companies across North America, with a focus on our San Jose office. You’ll build trust with executives, quantify ROI, and drive adoption of Whatfix’s AI-powered platform.

You’ll join a high-energy, in-office culture that values collaboration, equity incentives, and a fast-moving sales cadence. This role requires travel and a strong track record in enterprise SaaS sales.

Qualifications

• 3+ years SaaS enterprise sales with hunting, negotiating, and closing skills.
• Experience selling to CRM, HR, L&D, Procurement, and IT stakeholders.
• Willingness to travel 50%+.
• C-suite relationship experience.

Responsibilities

• Consult with enterprise prospects to architect Whatfix’s value proposition.
• Drive engagement, quantify ROI, and ensure customer success.
• Build brand awareness and generate a robust sales pipeline.
• Sell a category-leading solution and collaborate with leadership.

Skills

SaaS enterprise sales

Executive presence

CRM proficiency

Travel 50%+

Job description

Whatfix is an AI platform advancing the “userization” of enterprise applications, empowering companies to maximize the ROI of their digital investments. Technology needs adoption. It’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 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.

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.

This intelligence powers our entire product suite.

• Product Analytics uncovers friction and closes adoption gaps.
• Mirror allows employees to train in safe, simulated environments.

These are embedded with Whatfix AI Agents which supercharge creation, insights, and user guidance.

Our upcoming AI-first products are already creating a buzz in the market.

• 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.
• Whatfix Mirror 2.0 is the world’s only System plus Role simulation with a complete assessment to lead the Gen AI simulation category.

Together, these products reflect Whatfix’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.

Whatfix is bridging the gap between rapid technological change and human enablement—ensuring AI is not only embedded but also usable, trusted, and outcome-driven for every employee.

At Whatfix, we’re not just making software easier—we’re making AI work for people.

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

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

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.

Whatfix’s leadership is consistently recognized across top industry analysts and business rankings:

• Won the 2025 AI Breakthrough Award for the Overall AI-based Analytics Solution of the Year
• Only DAP to be recognized as a “Leader” across various DAP reports for the past 5+ years by leading analyst firms like Gartner, Forrester, IDC, and Everest Group.
• 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.
• Named a Gartner Customers’ Choice for DAP for the second year in a row (2024 and 2025)—the only vendor in the market to earn this distinction consecutively.
• 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%
• Stevie Award winner in the category (Bronze): Customer Service Department of the Year – Computer Software - 100 or More Employees.
• Winner of the ISG Paragon Innovation Award in partnership with Sophos (customer) for the EMEA region and finalist in the Transformation Award category.
• RemoteTech Breakthrough Awards winner for “Software Asset Management Solution of the Year”

These recognitions are matched by business performance:

• Highest-Ranking DAP on 2023 Deloitte Technology Fast 500™ North America for Fifth Consecutive Year
• Listed on the Financial Times & Statista's High-Growth Companies Asia-Pacific 2025 list.
• 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

Are you a seasoned sales hunter with a track record of landing and expanding enterprise deals? Do you thrive on cracking complex sales cycles and delivering game-changing solutions? Join Whatfix, a leading data-driven digital adoption platform, and help organizations maximize the ROI of their software.

At Whatfix, we live by the motto “Hustle Mode ON.” As an Enterprise Account Executive, you’ll sell directly to Fortune 500 companies across North America and drive our growth.

The Opportunity

• Consult with enterprise prospects to understand needs and architect Whatfix’s value proposition
• Drive engagement, quantify ROI, and ensure customer success
• Build brand awareness and generate a robust sales pipeline
• Sell a category-leading solution in a vast market
• Work closely with our Co-Founder and CRO for 1:1 mentorship and collaboration

Culture for Sales Experts

• Entrepreneurial, collaborative San Jose office with access to founders
• Partner with sales development, solutions consulting, marketing, and product teams
• Continuous learning and development opportunities
• Leverage our employee value proposition (full perks below)

What You’ll Bring

• 3+ years SaaS enterprise sales experience with proven hunting, negotiating, and closing skills (ARR $50K–$500K+)
• Strong executive presence with C-suite relationship experience
• Experience selling to CRM, HR, L&D, Procurement, and IT stakeholders
• Detail-oriented, proactive, and CRM-savvy
• Intellectual curiosity, energy, charisma, and customer-centric mindset
• Willingness to travel 50%+
• Uncapped incentives + equity plan
• Mac shop—work with the latest tech
• Unlimited PTO + paid maternity leave
• Medical, Dental, Vision: Whatfix covers 80% of premiums
• HSA: $1,000 individual / $2,000 family
• Monthly cell phone stipend + daily UberEats lunches
• Learning & Development benefits, team/company outings
• Relocation and sponsorship available

We believe the best ideas come from collaboration. Our teams work in-office 4 days a week to spark innovation, build community, and stay connected. U.S. teams start their days early to stay aligned across time zones, keeping collaboration high and evenings free! OTE range $250K to $280K.

We recognize the importance of flexibility in balancing personal and professional priorities. To support this, employees have the option to work from home up to two days each month.

Cultural Principles

Customer First | Empathy | Transparency | Fail Fast & Scale Fast | No Hierarchies | Deep Dive & Innovate | Trust as the Foundation | Do It as You Own It

Whatfix is an Equal Opportunity Employer and E-Verify participant, complying with all EEO and ADA regulations.