Sign up to access all features of our service.
  • Job search
  • Favorites
  • Create a CV
    New
  • Salaries
  • Subscriptions

Account Executive

Letter AI

Account Executive

Letter AI is the world's first unified revenue acceleration platform powered natively by generative AI. Our platform empowers sales teams at customers like Lenovo and Redpanda to ramp up faster with AI-powered training and coaching, instantly find and personalize collateral for customers, and engage their buyers with the industry's first AI Sales Room. We recently raised a $40M Series B led by Battery Ventures, with participation from existing investors including Y Combinator, Lightbank, Northwestern Mutual Future Ventures, Stage 2 Capital, and Formus. The round comes just four months after announcing our Series A, indicating a shift we're seeing in real time: revenue teams aren't asking for more content or tools. They're asking for better outcomes, and Letter AI is bringing those outcomes to life! We 10Xed our revenue last year and are looking for the best of the best in Chicago to join us on the adventure.

The Role

As an Account Executive at Letter AI, you will play a key role in driving our revenue growth. This is an opportunity to take full ownership of the sales cycle—from identifying leads to closing deals. You'll be working with complete autonomy in a rapidly growing market, significantly impacting the company's growth and your own career development. The freedom to build, experiment, and create your own sales strategies will be unparalleled, as you help shape the go-to-market (GTM) function in a dynamic AI-driven startup.

Why Join?
  • Exponential Growth Potential: Be part of an early-stage startup in a transformational space, where there's massive opportunity for expansion and your contributions can significantly influence the company's trajectory.
  • Autonomy & Impact: You'll have the freedom to make key decisions, experiment with new approaches, and truly own your role.
  • AI-Powered Platform: Work at the forefront of AI technology, helping sales teams deliver real impact with AI (see our work with Lenovo and Redpanda).
  • Build from the Ground Up: This is a rare opportunity to be part of something bigger, crafting and shaping the GTM function for a fast-growing startup (we're being recognized as the fastest-growing AI startup in Chicago!)
What You'll Do
  • Sales Cycle Ownership: Fully manage the sales cycle from prospecting to closing, driving revenue growth and building relationships with key decision-makers at target companies.
  • Tailored Sales Strategies: Develop and execute customized sales strategies that address the specific needs and pain points of potential customers.
  • New Business Generation: Identify and actively pursue new opportunities through outreach, networking, and creative lead generation strategies
  • Collaborative Partnership: Work closely with the CEO and other team members to iterate on sales approaches, messaging, and market feedback, directly influencing product and market strategy.
  • Lead Expansion in an Open Market: Take advantage of a greenfield opportunity to penetrate an underserved market, driving significant top-of-funnel activity and converting early adopters.
Qualifications for the Role
  • 3+ years of experience in SaaS sales or related fields
  • Experience selling global enterprise sales or enablement solutions is a strong plus
  • Proven track record of exceeding sales quotas and driving revenue growth
  • Ability to manage the complete sales cycle with a strategic approach
  • Strong interpersonal and communication skills with the grit to "figure things out" on the fly
  • Independent, proactive, and comfortable in a fast-paced, ambiguous startup environment
  • Ready to wear multiple hats and take on additional responsibilities as the company grows
How We Operate

At Letter AI, we operate by a set of core principles:

  • Customer-obsessed: Make your customers unreasonably happy and everything else will fall into place
  • Ambitious yet practical: Set big goals, but stay grounded with disciplined execution and ruthless prioritization
  • Direct yet kind: Never hold back from speaking your mind, but do so in a way that is kind to your colleagues
  • Driven yet humble: Push for excellence and deliver fast, but keep your humility

Join us on this exciting journey to build the world's next generational sales tech company. We look forward to hearing from you!

Vacancy posted 2 days ago
Similar jobs that could be interesting for youBased on the Account Executive in Chicago, IL vacancy
  • $187k - $252.9k

    The Amazon Web Services Professional Services (ProServe) team is seeking a dynamic ProServe Account Executive (PAE) to join our team at Amazon Web Services (AWS). In this role, you'll be responsible for engaging new and existing customers in the Financial with transformative... 
    Suggested
    Local area
    Flexible hours

    AmazonWebServices

    Chicago, IL
    17 hours ago
  • $119.1k - $142.2k

     ...incredible value to our customers.What is the opportunity?Are you ready to lead the charge in AI-driven customer service? As a Scale Account Executive, you will be a key member of the team leading the growth of our new business. We're building a world-class sales organization,... 
    Suggested
    Work at office
    Local area
    Immediate start
    Work from home
    3 days per week

    Intercom

    Chicago, IL
    3 days ago
  • $125k - $150k

    DescriptionAt FORM we’re looking for a dynamic and results-driven Enterprise Account Executive who can leverage their prior success and proven track record in hunting and closing new business opportunities at the enterprise level. You’ll bring a self-starting, proactive... 
    Suggested
    Full time
    Remote work
    Flexible hours

    Trax Retail

    Chicago, IL
    17 hours ago
  • $220k - $280k

     ...SLED) market. This person will join a growing Public Sector Field Sales team and will cover the Chicago region. The Enterprise Account Executive will play an integral role in developing the territory and will focus on formulating and executing a sales strategy within an... 
    Suggested
    Full time
    Live in
    Local area
    Work visa
    Flexible hours
    Shift work

    Verkada

    Chicago, IL
    3 days ago
  • $155k - $165k

     ...advertiser demand for the FOX Network’s national content.JOB DESCRIPTIONFOX Television Sales is seeking a driven and results-oriented Account Executive to grow advertising revenue across both broadcast television and digital platforms, including Connected TV (CTV) and streaming... 
    Suggested
    Full time
    Local area

    Fox

    Chicago, IL
    2 days ago
  • $133.6k - $200.4k

     ...will accept applications on an ongoing basis until the position is filled.What do you get to do in this position? The Territory Account Executive is responsible for developing, executing, and sustaining the market strategy to grow the Segment business within the assigned... 
    Ongoing contract
    Full time
    Temporary work
    Live in
    Local area
    Remote work
    Flexible hours

    Schneider Electric

    Chicago, IL
    4 days ago
  •  ...inclusive, and authentic workplace and are looking for teammates passionate about what we do!What We Need:Katz Digital is seeking an Account Executive to join their CTV team in Chicago or Detroit.As an Account Executive, you will be instrumental in driving our sales... 
    Full time
    Local area
    Flexible hours

    iHeartMedia

    Chicago, IL
    3 days ago
  •  ...mmDemonstrated history of working with BDRs on assigned prospect accounts to act on building a top-of-funnel pipeline, then actively...  ...services into IT (ie network ops, infosec)The Strategic Account Executive will help GSI/MSP and Fortune 500 companies to transform their... 

    NetBrain Technologies

    Chicago, IL
    2 days ago
  •  ...opportunity to put the global economy within everyone’s reach while doing the most important work of your career.What you’ll doAs an Account Executive, Existing Business, you’ll be managing existing relationships and identifying new opportunities to expand Stripe’s footprint... 
    Work at office

    Stripe

    Chicago, IL
    3 days ago
  • $99.5k - $189.35k

     ...are the future of Salesforce.Applications for this position will be accepted on an ongoing basis.The ExperienceAs an Enterprise Account Executive, you'll be responsible for developing and executing against a comprehensive account/territory plan as well as driving sales in... 
    Full time
    Remote work
    Flexible hours

    Salesforce

    Chicago, IL
    1 day ago
  • $150k - $171.5k

     ...is always a way to contribute: Acting with autonomy, having accountability and being open to new perspectives are essential to our continued...  ..., we can’t wait to meet you.WHAT YOU'LL DOAs an Account Executive on our Enterprise Retail team, you will manage the full sales... 
    Work at office
    Local area

    Braze

    Chicago, IL
    1 day ago
  • $252.7k - $297.29k

     ...mission. Checkr is recognized on Forbes Cloud 100 2025 List and is a Y Combinator 2024 Breakthrough Company.As an Enterprise Account Executive, you'll own new logo growth within Checkr's Enterprise segment (>5K employees). This is a full-cycle, high-complexity sales role... 
    Work at office
    Local area
    Remote work
    Relocation
    3 days per week

    Checkr

    Chicago, IL
    2 days ago
  •  ...same time, 75 percent of organizations report higher employee satisfaction and stronger in office engagement.As an Enterprise Account Executive, you will take this data into senior level conversations and turn it into action. You will drive net new growth primarily through... 
    Full time
    Work at office
    Visa sponsorship
    Work visa
    3 days per week

    GrubHub

    Chicago, IL
    1 day ago
  • $100k - $230k

     ...enterprises grow. We’re now expanding our WPP Open SaaS offering — and looking for an experienced, entrepreneurial Enterprise Account Executive to lead the charge. This is a unique role: you’ll be one of the first AE dedicated to this product in the US. You will work closely... 
    Contract work
    Work at office
    Local area

    WPP

    Chicago, IL
    3 days ago
  • Job DescriptionADP is hiring a Sales Representative: Major Accounts, Core.ADP Major Accounts supports mid to large, complex organizations...  ...sell ADP's suite of solutions (40+ products and services) to executives, and accurately forecast your sales pipeline. ADP is here to... 

    ADP - Automatic Data Processing

    Chicago, IL
    3 days ago
  • $85k - $170k

     ...employee under at least one plan and 80% for family premiums under all plansNationwide medical, vision and dental coverageHealth Saving Account (HSA) with annual employer contributions and Flexible Spending Account (FSA) with tax saving optionsExpanded mental health... 
    Full time
    Work visa
    Flexible hours
    Shift work

    Verkada

    Chicago, IL
    2 days ago
  • DescriptionAt CADDi, we are adding an experienced Enterprise Account Executive to our dynamic team. This team member will be critical to our expansion, which requires seasoned professionals capable of navigating complex sales cycles within the manufacturing industry. You... 
    Full time
    Remote work

    CADDi

    Chicago, IL
    3 days ago
  • $55k - $68k

     ...strategy, paid media, and every space in between. At RF Studio53, creativity knows no bounds.Ruder Finn is looking for a dynamic Account Executive who loves across a range of industries and account types, from big multinationals to powerful start-ups, with the flexibility... 
    Full time
    Work at office
    Flexible hours

    Ruder Finn

    Chicago, IL
    17 hours ago
  • $100k - $115k

    WHAT YOU’LL DOViant has an exciting opportunity on our Chicago sales team for a Account Executive to evangelize new business, generate awareness, and grow sales of our Viant DSP with a focus on independent agencies in the Chicago metro area. This is a tremendous opportunity... 
    Long term contract
    Work experience placement
    Local area

    Viant Technology

    Chicago, IL
    17 hours ago
  • $85.3k - $125k

     ...needs, and think outside the box to unlock new possibilities.Position Overview:The Enterprise Human Capital Management (HCM) Account Executives at Paylocity work in a fast-paced business environment that is very competitive and quota-driven, targeting enterprise companies... 
    Local area
    Remote work
    Work from home
    Worldwide

    Paylocity

    Chicago, IL
    4 days ago
  • $277k - $330k

    WHAT IS BOX?Box (NYSE:BOX) is the leader in Intelligent Content Management. Our platform enables organizations to fuel collaboration, manage the entire content lifecycle, secure critical content, and transform business workflows with enterprise AI. We help companies thrive...
    Work experience placement
    Live in
    Shift work

    Box

    Chicago, IL
    2 days ago
  • $110k - $115k

     ...deliver the best ad for every impression opportunity, merging creative and media for proven results. What We NeedWe need a proven Account Executive who can expand Yieldmo’s footprint within the Publicis Chicago/Detroit portfolio and brand advertisers while delivering... 
    Contract work
    Summer work
    Remote work
    Home office
    Flexible hours

    Yieldmo

    Chicago, IL
    17 hours ago
  • $150k - $180k

     ...leader in DEX, with recent investment activity valuing the company at $3 billion.Job DescriptionWe are looking for an Enterprise Account Executive to drive new business revenue across the North Central region. This is a high-impact, field-oriented role for a seller who can... 
    Work at office
    Immediate start
    Remote work
    Flexible hours

    Nexthink

    Chicago, IL
    4 days ago
  • The RoleWe are looking for an experienced Enterprise Account Executive to join our team. The right candidate for this position will have a demonstrated history of success and quota over-achievement selling to enterprise organizations (preferably selling software applications... 
    Work at office
    Local area
    3 days per week

    ThoughtSpot

    Chicago, IL
    2 days ago
  • $136.1k - $185.6k

     ...possible to pursue challenges you are passionate about, in industries you care about.Armanino is proud to be Among the top 20 Largest Accounting and Consulting Firms in the Nation and one of the Best Places to Work. We have a community of resources that are ready and... 
    Full time
    Contract work
    Local area
    Flexible hours

    Armanino

    Chicago, IL
    3 days ago
  • $152k - $177.5k

     ...customers  Demonstrate ability to position and advise to CISO level executives with industry Point-of-View business insights; Continue to...  ...with qualification frameworksA proven track record managing accounts in cloud or cybersecurity ecosystem to elevate the business Experience... 
    Full time
    Visa sponsorship

    Wiz

    Chicago, IL
    17 hours ago
  • Account Executive, Enterprise- USLocation: This role requires working from our Chicago or Boston office two days per week, or from one of our hub locations (Austin or New York City) twice a month in a co-working space.About the positionAs an Account Executive you will play... 
    Work at office
    2 days per week

    showpad

    Chicago, IL
    17 hours ago
  • $165k - $190k

     ...enterprise asset management, procurement and contract management, accounting and budgeting, billing and revenue management, permitting and...  ...community at OpenGov.com.Job Summary:The Enterprise Account Executive will lead all sales efforts within their assigned territory... 
    Contract work
    Work at office
    Local area
    Flexible hours

    OpenGov

    Chicago, IL
    2 days ago
  •  ...Daily, you will cultivate relationships with Human Resources and executive decision-makers, set appointments, gather leads from...  ...ADP associates to cultivate additional business within existing accounts; you will make life-long friendships here.Collaborate Daily. You... 

    ADP - Automatic Data Processing

    Chicago, IL
    3 days ago
  • $247k - $281k

     ...driving successful, long-term growth and customer satisfaction.We’re seeking a high-energy, hunter-focused Emerging Enterprise Account Executive to identify and secure new enterprise logos while strategically expanding our footprint within a select group of high-... 
    Work at office
    Local area
    Work from home
    Worldwide

    Asana

    Chicago, IL
    2 days ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Account Executive. Be the first to apply!