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

Sr Enterprise Sales Executive

$85k - $200k

Paychex

Enterprise Sales Representative

Paychex is reimagining how businesses manage their workforce by bringing payroll, HR, benefits, and advisory services together into a single connected HCM platform. As Paychex and Paycor come together, we're combining innovative technology, data-driven insights, AI, and human expertise to help organizations work smarter, support their people, and achieve better business outcomes. This is an exciting time to join our team as we continue to invest in innovation, simplify client experiences, and shape the future of work. At Paychex, you'll have the opportunity to grow your career, make a meaningful impact, and be part of something bigger as One Paychex.

Where Complexity Meets Structure and Top Performers Win

There is a reason enterprise buyers are moving to Paycor. We built something no one else in the market can replicate: AI-enabled enterprise technology backed by the deepest operational expertise in the HCM industry. Our platform is purpose-built for how enterprise HR and finance actually work. When you sell for Paycor, you are not asking buyers to take a leap of faith. You are bringing them the answer the market has been waiting for.

Enterprise Sales at Paycor is built for experienced sellers who want to operate at a higher level. You'll partner with organizations of 100+ employees, helping them solve complex workforce challenges through a modern, end-to-end HCM platform and service experience.

This is a true new-logo, advisory services role, focused on building a pipeline, running disciplined sales cycles, and closing high-impact deals. You'll work within a structured selling environment with defined territories, clear go-to-market plays, integrated sales support tools, and opportunities to develop Centers of Influence (COI) partnerships and expand your professional networkso you can focus on what matters most: winning.

Responsibilities

What You'll Do

  • Hunt and close net-new enterprise business with organizations 100 to 5,000+ employees across defined territories
  • Run disciplined full-cycle sales from executive-level prospecting through multi-stakeholder discovery, demo, and close
  • Build high-value solution bundles or standalone solutions across the full One Paychex Portfolio, including PEO, HR Solutions, Managed Payroll, Benefits, Retirement, Merchant Services, and more, while earning accelerators on every module you attach.
  • Partner with Solutions Engineers, RevOps, and a world-class channel ecosystem, including 700+ active broker relationships and financial services firms in a GTM team-selling environment, so you are never building alone.
  • Own your pipeline with rigorous forecasting, disciplined front-end prospecting, and deal control through the close.

What It Takes to Win

  • 5+ years of quota-carrying experience or complex B2B sales with a verifiable track record of hunting, building a pipeline, and closing
  • Proven ability to engage economic buyers at the C-level and navigate multi-stakeholder engagement
  • Experience selling into organizations of 100+ employees
  • High accountability, resilience, and ownership of results because this team sets high expectations and meets them

Why This Role

  • Unlimited earning potential tied to performance and results with a focus on career development
  • World-Class Club Experiences for Top Performers
  • Access to larger, more strategic deals with real business impact
  • More ways to win! We offer a broad portfolio of products and services beyond tech to increase deal size
  • An AI-Powered Platform That Closes Deals Faster
  • A Commission Plan Engineered for Top Performers

This Role Is for You If...

You have been closing at a high level, and you are ready for a bigger stage. You want a platform you can believe in, a comp plan that actually rewards your performance, and leaders who will develop you rather than just measure you. You want to be part of something still being built, where the work you put in this year shapes what this enterprise organization looks like in three.

Qualifications

  • H.S. Diploma - Required
  • Bachelor's Degree - Preferred
  • 5 years of experience in relevant professional sales.
  • 3 years of experience in HCM industry.
  • Driver's License - Required
  • Sales - Preferred
  • Assertiveness - Preferred
  • Business Acumen - Preferred
  • Strong Work Ethic - Preferred
  • Time Management - Preferred
  • Sales Prospecting - Preferred
  • Enterprise Sales - Preferred
  • Sales Strategy - Preferred
  • Customer Relationship Management - Preferred
  • Selling Techniques - Preferred
  • Closing (Sales) - Preferred
  • Go-to-Market Strategy - Preferred
  • Business To Business - Preferred
  • Market Share - Preferred
  • Cold Calling - Preferred

Compensation

In the spirit of pay transparency, we are excited to share that the compensation range for this position is typically between $85,000 - $200,000. This range includes base pay plus commissions but does not consider other components that make up the total rewards package for the position. If you are hired at Paychex, your overall compensation will be determined based on factors such as geographic location, skills, education, and/or experience which may result in total compensation outside of this range.

Live the Paychex Values

  • Act with uncompromising integrity.
  • Provide outstanding service and build trusted relationships.
  • Drive innovation in our products and services and continually improve our processes.
  • Work in partnership and support each other.
  • Be personally accountable and deliver on commitments.
  • Treat each other with respect and dignity.

What's in it for you?

  • We value your well-being: We provide over 21 comprehensive rewards, including medical coverage, virtual wellness classes, tuition reimbursement, 401(k) + employer match, adoption assistance, financial assistance, and much more.
  • We value your time: From paid time off to company holidays, culture days, and comprehensive work-life balance programs, we will ensure you have the flexibility you need to be your best.
  • We value your development: Our award-winning training and development programs empower our employees with ongoing learning opportunities to give you the building blocks to grow your career.
  • We value your perspective: Our company culture reflects the diversity of our employees. We want you to be you and your voice to be heard.
  • We value our communities: We offer paid time off for volunteerism and promote many company-wide and local initiatives that benefit organizations you care about.

Note: The benefits described apply to full-time employees. Benefits for part-time, contract, and intern roles may vary.

Not sure if you meet every requirement?

At Paychex, we know that great talent comes in many forms. If you're passionate about the role but don't check every box, we still encourage you to apply. You might be the right fit - either for this position or another opportunity with us.

Paychex is an equal opportunity employer. We are committed to fostering a respectful and inclusive workplace where all individuals are treated fairly and evaluated based on their qualifications, experience, and merit. We comply with all applicable federal, state, and local laws prohibiting discrimination in employment.

Paychex
Vacancy posted 2 days ago
Similar jobs that could be interesting for youBased on the Sr Enterprise Sales Executive in Chicago, IL vacancy
  • Pegasystems in Chicago seeks a Client Executive to lead enterprise sales engagements, acquire new logos, and expand our footprint with C-suite clients. You will drive the full sales cycle from pipeline creation to close for our AI-driven Customer Engagement solutions,... 
    Senior

    Pegasystems

    Chicago, IL
    3 days ago
  • $85k - $160k

     ...Overview Selling Company's products and services by developing new clients and increasing the client base to increase profits in the Core Sales, Human Resource Services Sales or Major Market Sales organizations. Responsibilities Leverage the Go-to-Market Sales Strategy to... 
    Senior
    Base plus commission
    Full time
    Contract work
    Part time
    Internship
    Local area

    Paychex Deutschland GmbH

    Chicago, IL
    3 days ago
  • $130k - $150k

     ...Cvent Enterprise Sales Team Opportunity Cvent is a leading meetings, events, and hospitality technology provider with more than 5,500...  ...Cvent's Enterprise Sales Team is growing and is seeking Sales Executives to join our team. Your primary responsibility will be to... 
    Senior
    Remote work
    Worldwide

    Cvent

    Chicago, IL
    2 days ago
  • $110k - $150k

    Stefanini North America and APAC in Chicago, IL is seeking a Business Development Executive to drive business growth through innovative sales strategies and relationship management. The ideal candidate should have a robust background in sales and a proven ability to engage... 
    Senior

    Stefanini North America and APAC

    Chicago, IL
    5 days ago
  • ADP is seeking a Sales Representative for Major Accounts in Chicago. This role involves selling human resources technology to mid-to-large organizations, managing complete sales cycles, and cultivating new business opportunities. The ideal candidate will have strong adaptability... 
    Senior

    ADP

    Chicago, IL
    1 day ago
  • $109.5k

     ...About the role:Are you an ambitious, driven and energetic sales professional? Do you have a proven track record of success...  ...the travel industry?We are currently expanding our team of Enterprise Sales Executives with the North American market. Based out of our offices in... 
    Work at office
    Remote work
    Worldwide
    Relocation package
    3 days per week

    Perk

    Chicago, IL
    1 day ago
  • $152k - $242k

     ...their fullest potential. Job SummaryThe AVP, Senior Principal Enterprise Architect - Data is CNA’s most senior individual contributor,...  ...domain disciplines. This role connects enterprise strategy with execution, drives cross-portfolio integration, and ensures architectural... 
    Senior
    Full time
    Work experience placement

    CNA Financial

    Chicago, IL
    2 days ago
  •  ...Principal, Strategic Program Management & Technology Transformation to lead enterprise programs across infrastructure modernization and cloud initiatives. You will build governance, dashboards, and executive reporting to drive strategic outcomes. This role partners with cross-... 
    Senior
    Work at office

    TransUnion

    Chicago, IL
    1 day ago
  •  ...Guidant, an internationally acclimed, trusted multi-faced orgiansation into Information Technology Custom Learning Services for Enterprises, Lateral Staffing Solutions, Information Technology Development & Consulting, Infrastructure & Facility Management Services and Technical... 
    Senior

    Career Guidant

    Chicago, IL
    1 day ago
  •  ...put AI to work for people.Job DescriptionThe Senior Solution Sales Executive will oversee market success of ServiceNow's Moveworks...  ...Management platform and create a single source of truth that allows enterprise processes to execute with uniform information.What you get... 
    Senior
    Work at office
    Immediate start
    Remote work
    Flexible hours

    ServiceNow

    Chicago, IL
    4 days ago
  • Job DescriptionThe Sales Executive reports directly to the Head of Field Sales within the H&B Sales department and is responsible for driving business growth across the small market territory segment (1-249 benefit-eligible employees). This role focuses on developing and... 
    Senior
    Night shift

    Inspira Financial

    Oak Brook, IL
    2 days ago
  • $120k - $130k

     ...OverviewMotorola Solutions, Inc., Enterprise Strategic Accounts Team...  ...global enterprise customers. The Sr. Strategic Enterprise Account...  ...including demand generation, sales, strategic account planning and...  ...Proactively engage Motorola Solutions executive sponsors to build strategic... 
    Senior
    Full time
    Remote work
    Relocation

    Indigo Vision

    Chicago, IL
    4 days ago
  •  ...Job Description Job Description Enterprise Sales Executive - Project Based, 100% Remote, Part Time Internal Title: Door Opener Job Type: Project-Based, Part-Time, 100% Remote, Flexible Hours Description: We are one of the best sales teams in the country... 
    Remote job
    Full time
    Part time
    Flexible hours

    Kopp Consulting

    Chicago, IL
    17 days ago
  • $100k - $200k

     ...Job Description Job Description Enterprise Sales Executive Location: Chicago Salary: $100,000-200,000 J oin the Options Sales Team! Who are Options? Options is the largest global financial technology company headquartered in Belfast. We are... 

    Options Technology

    Chicago, IL
    18 days ago
  • $100k - $125k

     ...safer future.Department OverviewThe Enterprise Resiliency and Security team provides...  ...exploratory conversation.We are seeking a Sr. Enterprise Account Executive to join our Noggin Enterprise Resiliency team. Reporting to the Area Sales Manager, you will be responsible for... 
    Senior
    Full time
    Immediate start
    Remote work
    Relocation

    Indigo Vision

    Chicago, IL
    4 hours ago
  • Medium is seeking a skilled sales professional to sell consulting services for Microsoft D365 solutions and the Power Platform to enterprise clients in the United States. This role involves leading the sales cycle, nurturing relationships with C-suite contacts, and growing... 
    Remote job
    Flexible hours

    Medium

    Chicago, IL
    4 days ago
  • Insight is seeking a Market Development Executive III for Cybersecurity Services, offering remote flexibility. The role requires proven sales expertise in cybersecurity, specifically within enterprise environments, guiding clients toward comprehensive security solutions... 
    Remote job

    Insight

    Chicago, IL
    2 days ago
  • $65k - $75k

    Cvent is seeking experienced Sales Executives to join our growing Enterprise Sales Team in Chicago. Your primary responsibility will involve developing and closing new business while managing relationships with key accounts. Ideal candidates will have a bachelor’s degree... 

    Cvent

    Chicago, IL
    5 days ago
  • A leading IT services firm is looking for an Enterprise Sales Executive to join their Sales team in Chicago, IL. This role involves leading the sales cycle, nurturing client relationships, and achieving significant revenue targets. Ideal candidates have 5-10+ years of... 

    Prolifics

    Chicago, IL
    4 days ago
  • $102k - $147k

    Gartner is looking for a Business Development Executive in Chicago, Illinois to expand their client base in the large enterprise segment. You'll engage C-Level executives and manage the entire sales cycle from outreach to conversion. The role offers a competitive salary... 

    Gartner

    Chicago, IL
    4 days ago
  • Sales Executive / Business Development (Enterprise Partnerships) WANT TO JOIN OUR TEAM? WE CAN'T WAIT. JOB DESCRIPTION Sales Executive / Business Development (Enterprise Partnerships) 100% Commission | Uncapped | Brands, Agencies, Enterprise Role Own new logo growth... 
    Remote work
    Flexible hours

    Digital Factory, Inc.

    Chicago, IL
    1 day ago
  • Convr is seeking a seasoned Business Development Executive to drive large enterprise deals in the commercial insurance space. You will engage with C-level...  ...using your extensive underwriting or software sales background. In this role you will network across departments... 

    Convr (formerly DataCubes)

    Chicago, IL
    5 days ago
  • $150k - $250k

    A leading tech firm in Chicago is seeking an experienced Enterprise Account Executive to drive sales in the manufacturing sector. This role involves strategic targeting of key accounts and engaging with C-suite stakeholders. The ideal candidate has extensive enterprise... 

    CADDi

    Chicago, IL
    3 days ago
  • A recruitment firm is seeking a Strategic Account Executive in Chicago to manage the sales cycle and drive expansion across B2B SaaS sales, particularly...  ...roles and has a proven track record in managing enterprise accounts. This position offers a unique opportunity to... 

    Trident Search

    Chicago, IL
    3 days ago
  • Concept Reply US is seeking a motivated sales professional to drive consulting services...  ..., along with Power Platform solutions to enterprise clients across the US. The role emphasizes relationship building with C-suite executives and taking ownership of the sales cycle to... 
    Remote job
    Flexible hours

    Concept Reply US

    Chicago, IL
    4 days ago
  • Cvent is seeking a seasoned Sales Executive to drive new logo acquisition and revenue growth for Enterprise Accounts in a remote-capable Chicago-based role. You will manage the full sales cycle from prospecting to closing, with collaboration across SDRs and Account Managers... 
    Remote job

    Cvent

    Chicago, IL
    1 day ago
  • Rubrik’s sales organization is a united group of elite cross-functional sales professionals...  ..., protecting the world's data.As a Sr. Sales Engineer, you will provide technical...  ...products to a targeted list of new & existing enterprise customer accounts across Illinois &... 
    Senior
    Local area
    Immediate start

    Rubrik

    Chicago, IL
    2 days ago
  •  ...what’s possible and goes after it. If you’re a consultative, enterprise deal hunter who loves navigating complex organizations, shaping...  ...stakeholder, multi-workstream pursuitsKey responsibilitiesBuild senior executive relationships and map complex buying centers—engage C‑suite... 

    Avanade

    Chicago, IL
    4 days ago
  •  ...traditional account management title. The SVP of Enterprise Account Management runs a team of...  ...owners who run account plans, lead executive business reviews, expand wallet share across...  ...Echo portfolio.Partner with Enterprise Sales leadership on handoffs from new logo close... 
    Senior
    Full time
    Temporary work
    Work at office
    Shift work

    Echo Global Logistics

    Chicago, IL
    4 days ago
  • $163k - $234k

     ...software company is seeking a Principal Solution Engineer to join their GTM team in Chicago. This role involves partnering with enterprise customers, leading workshops, and delivering customized product demonstrations. Candidates should have over 10 years in Solution... 

    Freshworks

    Chicago, IL
    5 days ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Sr Enterprise Sales Executive. Be the first to apply!