Director, Enterprise Sales (US Central)

Chicago, Illinois, United States | Full-time | Fully remote


Who are we?

Founded in 2013, by Khadim Batti and Vara Kumar, Whatfix enhances the self-service capability of software products and helps companies accelerate product adoption.

Whatfix is revolutionizing the way Application Support and Learning content is consumed, by providing contextual and interactive training inside applications, at the exact time a task is being performed.  The product helps accelerate product adoption and redefine the way companies onboard, train, and provide support to users. 

Over 100 Fortune 1000 enterprises worldwide already trust Whatfix to reduce the time-to-value of business applications and improve users productivity and performance.

We are looking for exceptionally talented and motivated individuals to help us build the world’s best software at scale for thousands of clients. Join us as we reinvent the product adoption cycle.

What sets Whatfix apart? 

  • $140million in funding, most recently a $90mm Series D from investors like Sequoia Capital, SoftBank, Stellaris, Cisco, and Eight Roads
  • With over 100 of the Fortune 1000 already onboard as customers, Whatfix has been named among the top 20 B2B tech companies alongside the likes of Adobe, PayPal, and Cisco
  • Exponential sales growth, with Q1 ‘21 sales up 140% from Q1 ‘20, and Q2 ‘21 sales up over 150% from Q2 ‘20.  
  • Gartner and Everest Research recognize Whatfix as a Global Market Leader in the digital adoption space 
  • Customer rating of 4.7+ on platforms like G2 Crowd & Gartner Peer Insights

About the Role

  • The Director, Enterprise Sales (US Central) is a team quota carrying position. As a leader - you, along with a high-performing team (reporting to you), will lead our new-logo hunting strategy in a named set of Enterprise Accounts.
  • The regional leader will empower, set goals & strategy and hold the team accountable for quota attainment as well as lead by example, by serving as a player/coach on key accounts & owning some opportunities. This strategic leader collaborates with the AEs in closing new enterprise clients.
  • This leader is a player, mentor as well as a coach; and, is an evangelist for the needs of the business.


  • Manage, build & scale a world-class Account Executive team based out of the US Central territory. Help drive pipeline & close business to grow overall revenue of Whatfix within assigned territory.
  • Coach AEs through the development of key Enterprise level sales skills including forecasting & sales planning, prospecting within account base, complex deal negotiations, sales closures and cross-functional support both internally & externally
  • Directly own prospecting activities, build pipeline and drive opportunities individually as well in a small set of accounts; be a hands-on player while managing a team
  • Assesses sales pipeline, activity & forecasts to determine sales progress & areas for refinement/improvement
  • Develop proven and new strategies with AEs to further penetrate Enterprise Accounts and reinforce process and steps designed to deliver value at enterprise scale 
  • Maintain proactive line of communication with other cross functional leaders as well as senior leadership; includes developing and delivering accurate forecast and attainment details during weekly and other regular updates
  • Responsible for performance management and growing the team headcount as needed. Identifies & supports opportunities for training as well as career growth across the team 
  • Operates well in a fast-paced, dynamic environment without requiring supervision. Can think creatively and independently to resolve conflict as well as solve problems 


  • 8+ years of work experience with 3+ years of proven experience in building & leading a successful enterprise sales / account management team at SaaS or IT Services company
  • 5+ years experience selling software in a quota-carrying position within large Fortune 500 enterprise accounts with proven ability to hunt for new opportunities 
  • Experience selling to buyers from CRM, HR, Learning and Development, Procurement and/or IT for Software Applications managing complex sales cycle and opening doors
  • Track record of building, coaching and enabling a rapidly growing team 
  • Value based solution selling ability and understanding of ROI and cost/benefit analysis
  • Consistent track record of over achievement, exceeding quota, and high performance
  • Strong executive presence and ability to develop executive level (CxO) relationships and lead strategic initiatives with customer
  • Experience structuring and executing on Enterprise Level Agreements at Enterprises
  • Excellent communication, negotiations and strategic thinking skills
  • Able to work remotely with other members of your team & supervise effectively
  • Ability to travel domestically and internationally as needed. Expect up to 25 to 30% travel
  • Intellectually curious - you ask open-ended questions and are genuinely interested in learning your partners and customers needs
  • Cross-cultural – you like working with many types of people across multiple geographies and languages
  • You believe in what Whatfix is creating (a new category) and you understand how to build partnerships and solutions that support the long-term vision

You would be an excellent fit for our team if:

  • You are a self-motivated, high performing sales leader who works in hustle mode to get the job done
  • You’re comfortable selling at a start-up company that is emerging in the market and you are excited about putting your mark on something early
  • You love being a part of a small, dynamic, and agile organization that encourages you to learn and grow
  • You are passionate about using your experience and expertise to inspire the team

Perks / Benefits

  • Uncapped incentives and bonus plan
  • Scope to Represent Whatfix at events like Dreamforce, SAP Sapphire, SaaStr and several other marquee events
  • Unlimited PTO policy
  • Medical, Dental, and Vision coverage
  • 401 K Plan


We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.



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