Pilot AI

Turns your sales calls into CRM data, automatically.

Founding Enterprise Account Executive

$100K - $200K / 0.15% - 0.25%
San Francisco, CA, US / New York, NY, US / Remote (US)
Job Type
3+ years
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Max Lu
Max Lu

About the role

About Pilot AI

At Pilot AI, we are building the future of sales technology by using AI to unleash all of the information locked away in meetings, emails and calls for automation, insights and coaching. The days of fiddling with pick-lists in Salesforce and endlessly trying to craft the perfect followup email are over. Pilot AI fills out every CRM field automatically the moment the meeting is over and so much more. Our customers include Vouch, Deepgram, Fleet Space and other companies across a wide range of industries.

Pilot AI is backed by the top founder and silicon valley VCs including YC, Soma Capital, Pioneer Fund, Emmett Shear (Twitch), Aarash Ferdowsi (Dropbox), Samvit Ramadurgam (Forge).

We are on a mission to build the technology that will power and inform the next generation of sales organizations and empower the next generation of superstar sales reps.

Role & Responsibilities

If you thrive on closing deals, learning and are looking for an opportunity to make a significant impact, this role could be a perfect fit.

  • Run a full-cycle enterprise sales process
    • Hunt for and prospect into new logos and build a named accounts list
    • Build and execute account plans to win your named accounts - identify key decision makers, buying processes, and close deals
    • booking and owning discovery calls
    • Navigate an enterprise to map stakeholders, build champions, generate buy-in and close deals with C-Level decision makers
      • The instincts to recognize organizational financial and behavioral structures and obstacles
      • Exhibit business acumen and strategic thinking on a high level, with the ability to go deep into an account, and consult on and align with their global strategy
    • Be a consultative trusted advisor for the customer by building in-depth relationships and understanding the business goals and objectives
    • running product demos
    • negotiating terms
    • signing contracts
    • Onboard the customer onto Pilot AI (With support from the team)
    • Meet or exceed monthly, quarterly and yearly revenue targets
  • Develop deep knowledge of our products and clearly articulate their value proposition to stakeholders at all levels
    • Exhibit deep and up-to-date knowledge of our product portfolio to communicate the benefits of new features and enhancements
  • Establish and nurture lasting relationships with stakeholders and decision-makers at both prospects and customers
  • Establish credibility and trust with front line leaders and executives by demonstrating strong business acumen and understanding of workflows and pain points
  • Capture feedback from prospects on their needs, wants, and pains, and share that feedback with product and engineering teams to develop our product roadmap
    • Represent both market trends and client needs to the Executive and the Product teams to ensure we are both serving current needs well and evolving our products and portfolio to identify future client needs
  • Iterate on goals, strategies, and tactics to close new logos in new industries
  • Test sales motions, pitches, value props, provide feedback on what tactics are most effective and develop and recommend sales strategies
  • You may be asked to travel and represent Pilot AI at national and regional industry conferences


  • You enjoy planning, adjusting, executing, winning, and celebrating as a team
  • Proven top performer as a quota carrying rep with a consistent track record of overachieving quota
  • 3+ Years of selling in the enterprise segment
  • Extreme ownership: Your job isn’t done until the job is done.
  • Hunter mentality with solid Sales DNA and appetite for continual learning
  • Competitive, tenacious & persistent: You love winning and relish doing what it takes
  • Resourceful, scrappy & creative: you look for ways through problems and refuse to let obstacles derail your progress.
    • A creative mindset with the ability to think outside the box to complex situations
  • Adaptability: You can adapt to changing conditions on the fly to achieve your goal
  • Proactive, self-sufficient & relentlessly driven
  • Execution Focused
  • You are used to uncovering pain points and building value in competitive situations.
  • Ability to navigate large organizations’ political landscape to maintain and expand relationships at all levels
  • Extreme Curiosity: digging and digging and not being satisfied until you truly understand the root cause
  • You must have a strong sense of urgency and ability to excel in a fast paced and dynamic environment
  • Excellent communication and interpersonal skills, with ability to cultivate stakeholder relationships
  • Excellent written and verbal communication skills - able to simplify complex topics in a friendly and approachable manner
  • Critical thinker, extremely curious and persistent, with strong ability to conduct deep discovery, challenge assumptions and handle objections
  • Must be based in North America, with ability and willingness to occasionally travel (for example to conferences and prospect visits and offsites)
  • A track record of developing a greenfield territory, adding net new logos in an Enterprise software role
  • Demonstrated ability to generate and execute against a plan to ensure deep penetration into and closing of enterprise accounts

Nice to Have

  • Have experience selling into sales organizations interfacing with all stakeholders from individual sales reps to manager, revenue operations to the VP sales and CRO. This includes being ****capable of engaging in business and technical conversations
  • You have an in-depth understanding of the buyer journey and can lead a complex, multi-party sale in a highly consultative manner, deeply understanding their sales organization and how a product like Pilot AI can be a critical component of that.

Why you should Apply

Join a world-class team in a booming space on the ground floor to do your best work ever, grow faster than you ever have, and have a blast while doing it!


Compensation is $100K base and 10% commission.

About Pilot AI

At Pilot AI, we are building the future of sales technology by using AI to unleash all of the information locked away in meetings, emails and calls for automation, insights and coaching.

Pilot AI
Team Size:3
Location:San Francisco
Max Lu
Max Lu