Strategic Enterprise Account Executive

Rippling; Chicago (IL); On-site; USD 306,000 - 414,000; Full time

Job summary

Rippling is seeking a Senior Enterprise Account Executive to drive transformational growth with large, complex organizations using our unified HR/IT/Finance platform.

You will navigate multi-stakeholder buying groups, manage a $1M+ annual quota, and lead strategic evaluations from first engagement through close and customer launch.

Join a fast-paced team that rewards curiosity, rigor, and the ability to align product value with executive priorities across the enterprise.

Qualifications

• 6+ years selling SaaS/HCM/Payroll/Platform to C-levels
• Experience carrying a $1M+ annual quota
• Top 10% sales performance history
• Proven outbound acquisition sales
• Experience selling Payroll and HRIS/HCM software to business users
• Experience negotiating with C-Suite executives
• Programmatic lead generation in assigned accounts
• Thrives in fast-paced environments
• Strong verbal and written communication skills

Responsibilities

• Sell into large prospects above 1000 employees
• Become product expert across Rippling platform and understand competitor landscape
• Develop strategy for prioritizing, targeting, and closing opportunities
• Account planning with SDR to generate pipeline
• Lead sales calls with discovery, qualification, and demos
• Coordinate with sales engineering for up-market needs
• Lead pre-sales and internal resources for multi-team cycles
• Use MEDDPICC to qualify and navigate sales cycles
• Manage Salesforce pipeline and monthly/quarterly forecasts
• Achieve quota attainment consistently

Skills

SaaS sales

C-level selling

Quota attainment

Outbound sales

Sales strategy

Negotiation

Lead generation

Tools

Salesforce

Job description

About this position

About Rippling

Rippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system.

Take onboarding, for example. With Rippling, you can hire a new employee anywhere in the world and set up their payroll, corporate card, computer, benefits, and even third-party apps like Slack and Microsoft 365—all within 90 seconds.

Based in San Francisco, CA, Rippling has raised $1.2B from the world’s top investors—including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock—and was named one of America's best startup employers by Forbes.

We prioritize candidate safety. Please be aware that all official communication will only be sent from @ Rippling.com addresses.

About the role

The Strategic Enterprise Account Executive role at Rippling is one of the fastest-growing segments of our business and a cornerstone of our move upmarket. This is a unique opportunity to drive transformational growth by helping large, complex organizations modernize how they manage HR, IT, and Finance in one unified platform.

We’re looking for ambitious, high-performing Account Executives who can navigate multi-stakeholder, strategic sales cycles. From first engagement through close and customer launch through our implementation approach.

At Rippling, we believe AEs should spend 100% of their time where they create the most impact:

• Engaging with qualified prospects and executive buyers
• Managing strategic evaluations that showcase Rippling’s differentiated value
• Project managing high-value opportunities sourced from a mix of inbound and outbound motions
• Partnering closely with Implementation and Support teams to ensure a seamless transition and long-term customer success

This role is a fit for sellers who thrive in complexity, lead with curiosity, and want to shape how Rippling wins in the enterprise market.

What you will do

• Sell into our largest, most strategic prospects above 1000 employees
• Become a product expert across our entire platform and understand our competitor landscape
• Develop strategy for prioritizing, targeting, and closing key opportunities in assigned accounts
• Perform account planning for prioritized accounts, and work in tandem with your assigned Sales Development Representative to generate pipeline.
• Run sales calls with presentations, detailed solution discovery, qualification rigor, and customized product demos
• Work with our sales engineering teams to provide up-market insights to inform Rippling of customer needs that we need to be prepared to meet in selling to larger companies.
• Leading pre-sales and other internal resources to ensure alignment when leading a broader group to assist with sales cycles.
• Utilize MEDDPICC sales methodology to qualify opportunities and comprehensively navigate the sales cycles.
• Manage pipeline in Salesforce to accurately forecast revenue on a monthly and quarterly basis
• Achieve quota attainment consistently

What you will need

• 6+ years of experience selling SaaS/HCM/Payroll/Financial or Platform solutions to C-levels from a field sales position
• Experience carrying a $1M+ annual quota
• Track record of success (top 10% of sales org)
• Proven track record of outbound acquisition sales
• Experience selling Payroll and HRIS/HCM software and or a B2B platform to business users
• Experience negotiating deals with a variety of C-Suite Executives to close opportunities
• Experience in engaging in a programmatic approach to generate and develop leads within your assigned accounts
• Ability to thrive in a very fast paced environment
• Strong verbal and written communication skills

Even if you don’t meet all of the requirements listed here, we still encourage you to apply. Skills can be used in lots of different ways and your life and professional experience may be relevant beyond what a list of requirements will capture.

Rippling is an equal-opportunity employer. We are committed to building a diverse and inclusive workforce and do not discriminate based on race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, sexual orientation, veteran or military status, or any other legally protected characteristics. Rippling is committed to providing reasonable accommodations for candidates with disabilities who need assistance during the hiring process. To request a reasonable accommodation, please email [e-mail].

Rippling highly values having employees working in-office to foster a collaborative work environment and company culture. For office-based employees (employees who live within a 40 mile radius of a Rippling office), Rippling considers working in the office, at least three days a week under current policy, to be an essential function of the employee's role.

This role will receive a competitive On-Target Earnings (base salary + sales commission) + benefits + equity. The On-Target Earnings* for US-based employees will be 50/50 commission split for base/variable pay, and aligned with one of the ranges below based on location; see which tier applies to your location here .

A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed below.

*Commission is not guaranteed

The pay range for this role is:

$360,000 OTE