Lead Enterprise Account Executive Chicago
Lead Enterprise Account Executive Chicago

Lead Enterprise Account Executive Chicago

Full-Time 100000 - 120000 £ / year (est.) No home office possible
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At a Glance

  • Tasks: Drive new business and nurture existing client relationships in a dynamic sales environment.
  • Company: Join Culture Amp, the leading employee experience platform transforming workplaces globally.
  • Benefits: Enjoy flexible work options, equity opportunities, wellness support, and generous time off.
  • Why this job: Be part of a mission-driven company that values diversity and fosters personal growth.
  • Qualifications: 8+ years in sales, preferably in SaaS or HR Tech, with strong communication skills.
  • Other info: We encourage diverse candidates to apply, even if you don't meet every requirement.

The predicted salary is between 100000 - 120000 £ per year.

Join us on our mission to make a better world of work.

Culture Amp is the world’s leading employee experience platform, revolutionizing how 25 million employees across more than 6,500 companies create a better world of work. Culture Amp empowers companies of all sizes and industries to transform employee engagement, drive performance management, and develop high-performing teams. Powered by people science and the most comprehensive employee dataset in the world, the most innovative companies including Canva, On, Asana, Dolby, McDonalds and Nasdaq depend on Culture Amp every day.

Culture Amp is backed by leading venture capital funds and has offices in the US, UK, Germany and Australia. Culture Amp has been recognized as one of the world’s top private cloud companies by Forbes and most innovative companies by Fast Company.

This role bridges the responsibilities of acquiring new customers and fostering growth within an existing book of business. As a consultative, strategic advisor, the Account Executive will leverage deep product knowledge, customer insights, and a results-driven approach to drive new business acquisition (60%) while ensuring customer retention and expansion (40%). The role amplifies Culture Amp’s mission by creating impactful partnerships and delivering measurable ROI to clients.

In this role you will:

New Business Acquisition (60%)

  • Proactively identify and engage potential customers through a mix of outbound calls, emails, LinkedIn, and attendance at marketing events (virtual and in-person).
  • Creation of specific points of view (POV’s) on their identified ‘lighthouse accounts’.
  • Run tailored product demonstrations for People Leaders, establishing credibility and highlighting Culture Amp’s competitive differentiators.
  • Build and manage a robust sales pipeline, expertly guiding prospects through the sales process from discovery to close.
  • Develop and present compelling business cases for prospects to adopt Culture Amp’s platform, leveraging insights and ROI calculations.
  • Collaborate with internal stakeholders (e.g., legal, procurement, and security teams) to remove barriers and streamline deal closure.
  • Maintain accurate pipeline and forecasting data in Salesforce and other tools to meet quarterly new business quotas.

Customer Retention & Expansion (40%)

  • Serve as a trusted advisor for existing customers, driving retention by proactively identifying risks and implementing tailored mitigation plans.
  • Creation of tailored Account Plans that help serve as a north star for the GTM functions.
  • Conduct regular strategic reviews, leveraging data-driven insights to uncover expansion opportunities and optimize customer engagement with the platform.
  • Build a sustainable pipeline of upsell and cross-sell opportunities, converting them into closed-won deals to achieve expansion targets across a rolling 6 month period.
  • Establish multi-threaded relationships with key stakeholders, fostering deeper connections to ensure long-term loyalty.

You have:

  • 8+ years of sales experience with a focus on either new or expansion (or both) driven revenue targets.
  • Proven experience in the SaaS space, particularly within HR Tech or related fields.
  • Strong ability to identify and self-source both new and expansion opportunities, employing innovative strategies.
  • Exceptional executive presence with polished presentation and communication skills, particularly when engaging with VP and C-suite executives.
  • Experience building and navigating relationships within enterprise environments.
  • Familiarity with sales methodologies, such as MEDDPICC, and a solid understanding of deal stage progression.
  • Proficiency in leveraging data for decision-making and influencing others.
  • Skilled in assessing business opportunities and understanding diverse buyer personas.
  • Proven track record in orchestrating the closure of business deals with a clear understanding of customer needs.
  • Experience coordinating cross-functional teams (Solution Consulting, Security, Legal) through complex sales cycles.

For this role, the estimated base salary range is listed below. In addition to base salary, your compensation package will include additional components such as equity and benefits. For sales roles, your package may also include sales commission.

The actual base salary will vary based on various factors, including market and individual skills, capabilities and experience, objectively assessed during the interview process. If you\’re interviewing for this role, speak with your Talent Acquisition Partner to learn more about the total compensation and benefits for this role.

Base Salary Range (US): $138,000 – $162,000 USD

For this role, the estimated On Target Earnings (OTE) range is listed below. In addition to your OTE salary, your compensation package will include additional components such as equity and benefits.

OTE Salary (US): $230,000 – $270,000 USD

We believe that our employees are the heartbeat of our success. We\’re committed to fostering a work environment that truly cares for and develops its people, and creates lasting positive impact. In addition to providing a competitive compensation package, some of the key benefits we offer are:

  • Employee Share Options Program: We empower you to be an owner in Culture Amp and share in our success.
  • Programs, coaching, and budgets to help you thrive personally and professionally.
  • Access to external providers for mental wellbeing and coaching support to sustain the wellbeing, safety and development of our people.
  • Monthly Camper Life Allowance: An automatic allowance paid out each month with your pay – you can spend it however you like to help improve your experience and life outside work.
  • Team budgets dedicated to team building activities and connection.
  • Intentional quarterly wellbeing pauses: A quarterly company-wide shutdown day in each region to collectively pause, reset and focus on restoration and rest, without having to tap into individual vacation time.
  • Extended year-end breaks: An extended refresh period at the end of year.
  • Excellent parental leave and in work support program available from day 1 of joining Culture Amp.
  • 5 Social Impact Days a year to make a positive impact on the community outside of work.
  • MacBooks for you to do your best & a work from home office budget to spend on setting up your home office.
  • Medical insurance coverage for you and your family (Available for US & UK only).

Additionally, we don\’t just focus on our internal community; we believe in creating a better world of work for all. We\’re committed to diversity, equity, and inclusion, with Employee Resource Groups and ally communities in place.

We have a strong commitment to Anti-Racism, and endeavor to lead by example. Every step we make as a business towards anti-racism is another step we can take to support our customers in making a better world (of work).

Please keep reading…

Research shows that candidates from underrepresented backgrounds often don\’t apply for roles if they don\’t meet all the criteria – unlike majority candidates meeting significantly fewer requirements.

We strongly encourage you to apply if you’re interested: we\’d love to know how you can amplify our team with your unique experience!

Thank you for taking the time to read this advert. If you decide to apply, as part of your application, we will ask you to complete voluntary diversity questions (excluding Germany).

If you require reasonable accommodations or adjustments due to a disability to complete the online application or to participate in the interview process, please contact and identify the type of accommodation or assistance you are requesting. Do not include any medical or health information in this email. The Reasonable Accommodations team will respond to your email promptly.

Culture Amp will retain your CV & personal information for a period of two years (four years for the US) from the date of your application process completion. Culture Amp may contact you in relation to future job opportunities during this time period. For further information please see our privacy policy here or contact

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Global Diversity Questions

At Culture Amp, we are incredibly proud of how our platform helps companies measure aspects of diversity and inclusion; particularly aspects beyond race and gender. When it comes to measuring diversity for ourselves, we are leading the charge in helping companies think about building balanced teams.

To get a comprehensive understanding of our pipeline, we invite all applicants to fill out these demographic questions. Completion of this form is entirely voluntary and declining to provide this information will not subject you to adverse treatment.

By providing answers in the following questionnaire you consent to Culture Amp using your anonymised demographic information for internal research and trend analysis.

Culture Amp is committed to providing equal employment opportunities to all employees and applicants for employment regardless of race, colour, religion, creed, age, national origin or ancestry, ethnicity, sex, sexual orientation, gender identity or expression, disability, military or veteran status, or any other category protected by federal, state, or local law.

Thank you and good luck with your application.

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Lead Enterprise Account Executive Chicago employer: Culture Amp

Culture Amp is an exceptional employer that prioritises employee wellbeing and professional growth, offering a competitive compensation package alongside unique benefits such as an Employee Share Options Program and intentional quarterly wellbeing pauses. With a strong commitment to diversity, equity, and inclusion, Culture Amp fosters a collaborative work culture where employees are empowered to make a meaningful impact both within the company and in the wider community. Located in the vibrant Flatiron neighbourhood of Chicago, this role provides the opportunity to work with innovative companies while contributing to a mission that transforms the world of work.
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Contact Detail:

Culture Amp Recruiting Team

StudySmarter Expert Advice 🤫

We think this is how you could land Lead Enterprise Account Executive Chicago

✨Tip Number 1

Familiarise yourself with Culture Amp's platform and its unique selling points. Understanding how their employee experience solutions work will allow you to speak confidently about the product during interviews and demonstrate your ability to engage potential clients effectively.

✨Tip Number 2

Network with current or former employees of Culture Amp on LinkedIn. Engaging with them can provide valuable insights into the company culture and expectations, which can help you tailor your approach and show that you're a good fit for the team.

✨Tip Number 3

Prepare specific examples from your past sales experiences that highlight your success in acquiring new customers and expanding existing accounts. Be ready to discuss how you used data-driven insights to drive results, as this aligns closely with the role's requirements.

✨Tip Number 4

Research the key players in the HR Tech space and understand the competitive landscape. Being able to articulate how Culture Amp stands out from its competitors will demonstrate your strategic thinking and ability to position the product effectively during client interactions.

We think you need these skills to ace Lead Enterprise Account Executive Chicago

Sales Strategy Development
Consultative Selling
Customer Relationship Management
Pipeline Management
Data-Driven Decision Making
Presentation Skills
Negotiation Skills
Account Management
Cross-Functional Collaboration
Understanding of SaaS and HR Tech
Executive Communication
Risk Identification and Mitigation
Business Case Development
Sales Methodologies (e.g., MEDDPICC)
Market Research and Analysis

Some tips for your application 🫡

Tailor Your CV: Make sure your CV highlights relevant experience in sales, particularly in the SaaS and HR Tech sectors. Emphasise your achievements in new business acquisition and customer retention, as these are key aspects of the role.

Craft a Compelling Cover Letter: Use your cover letter to showcase your understanding of Culture Amp's mission and how your skills align with their goals. Mention specific examples of how you've successfully driven revenue and built relationships in previous roles.

Highlight Relevant Skills: In your application, focus on skills that are crucial for this position, such as consultative selling, relationship building, and data-driven decision-making. Mention any familiarity with sales methodologies like MEDDPICC.

Showcase Your Impact: Provide quantifiable results from your past experiences. For instance, mention how you increased sales or improved customer retention rates. This will demonstrate your ability to deliver measurable ROI, which is essential for the role.

How to prepare for a job interview at Culture Amp

✨Know Your Product Inside Out

As a Lead Enterprise Account Executive, you'll need to demonstrate deep product knowledge. Familiarise yourself with Culture Amp's platform and its unique features. Be prepared to discuss how it can solve specific problems for potential clients.

✨Prepare for Consultative Selling

This role requires a consultative approach. Practice how to ask insightful questions that uncover client needs and tailor your pitch accordingly. Show that you can act as a strategic advisor rather than just a salesperson.

✨Showcase Your Sales Methodology Knowledge

Familiarity with sales methodologies like MEDDPICC is crucial. Be ready to explain how you've applied these frameworks in past roles to successfully close deals and manage complex sales cycles.

✨Build Rapport with Stakeholders

Establishing relationships with key stakeholders is essential for success in this role. Prepare examples of how you've built and maintained relationships in previous positions, especially within enterprise environments.

Lead Enterprise Account Executive Chicago
Culture Amp
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  • Lead Enterprise Account Executive Chicago

    Full-Time
    100000 - 120000 £ / year (est.)

    Application deadline: 2027-08-24

  • C

    Culture Amp

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