Large Enterprise Sales Development Representative

Company: Paylocity
Location: Schaumburg
Posted on: February 15, 2026

Job Description:

Job Description Job Description Description: Paylocity is an award-winning provider of cloud-based HR and payroll software solutions, offering the most complete platform for the modern workforce. The company has become one of the fastest-growing HCM software providers worldwide by offering an intuitive, easy-to-use product suite that helps businesses automate and streamline HR and payroll processes, attract and retain talent, and build a strong workplace culture. While traditional HR and payroll providers automate basic HR processes such as payroll and benefits administration, Paylocity goes further by developing tools that HR and businesses need to compete for talent and deliver against the expectations of the modern workforce. We give our employees what they need to succeed, including great benefits and perks! We offer medical, dental, vision, life, disability, and a 401(k) match, as well as perks that support you, your family, and your finances. And if it’s career development you desire, we provide that, too! At Paylocity, people matter most and have always been at the heart of our business. As part of the Sales & Marketing team, you’ll help us solve challenges and succeed as you grow and understand the unique needs of our clients and tailor easy-to-use solutions to deliver the performance they need. With a position in Sales & Marketing, you’ll strengthen our relationships with clients, anticipate their needs, and think outside the box to unlock new possibilities. Fully Remote (U.S. Only): This is a fully remote position, allowing you to work from home or location of record within the U.S. with no in-office requirements. You must be available five days per week during designated work hours. The work arrangement for this role is subject to change based on business needs and individual performance. This may include adjustments to on-site requirements or schedule expectations, as necessary. Position Overview: This role is responsible for generating qualified pipeline opportunities within large, complex organizations (1,500 employees). This role focuses on early-stage engagement, identifying prospects, conducting outreach, qualifying business needs, and scheduling discovery conversations for the Large Enterprise Sales team. The ideal candidate is motivated, curious, and able to build rapport with senior HR, Finance, Payroll, and IT leaders. Primary Responsibilities The below represents the primary duties of the position, others may be assigned as needed. To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. Prospecting & Pipeline Generation Research and identify target accounts within the Large Enterprise segment using industry data, organizational insights, and strategic priorities. Engage prospective customers through multi-channel outreach including phone, email, LinkedIn, and events. Craft tailored messaging that communicates the value of HR and payroll solutions and addresses enterprise-level challenges. Build and maintain a healthy pipeline of qualified opportunities for Large Enterprise Account Executives. Discovery & Qualification Conduct high-level needs assessments to understand customer pain points in HR, Talent, Payroll, Workforce Management, and related functional areas. Qualify opportunities using proven methodologies (e.g., MEDDICC) to assess fit, intention, and urgency. Document all interactions, insights, and next steps in CRM systems with accuracy and discipline. Collaboration & Alignment Partner closely with Large Enterprise Sales Executives, Marketing, and Sales Operations to align on target lists, campaigns, and go-to-market strategies. Provide feedback on messaging effectiveness, customer trends, and competitor insights. Support enterprise campaigns, webinars, and events by driving attendance and engaging prospects. Performance & Growth Consistently meet or exceed activity and pipeline generation targets. Demonstrate strong business acumen and continuously deepen knowledge of HCM market trends and enterprise customer needs. Engage in ongoing training and development to advance toward future roles in enterprise sales Education and Experience: 6 of experience in sales development, business development, or customer-facing roles—preferably in SaaS or enterprise technology. Strong written and verbal communication skills, especially when interacting with senior-level stakeholders. Proven ability to manage outbound prospecting and generate qualified interest in complex, multi-solution offerings. Experience using CRM systems (e.g., Salesforce), sales engagement tools (e.g, Salesloft), and prospecting platforms. Preferred: Experience in HCM, HR technology, ERP, SaaS, or workforce solutions. Familiarity with large enterprise organizational structures and buying cycles. Strong research, prioritization, and time-management skills. Ability to thrive in a fast-paced environment with high expectations for performance. Paylocity is an equal-opportunity employer. Paylocity is committed to the full inclusion of all individuals. We recruit, train, compensate, and promote regardless of race, religion, color, national origin, sex, disability, age, veteran status, and other protected status as required by applicable law. At Paylocity, we believe diversity makes us better. We embrace and encourage our employees’ differences in age, culture, ethnicity, family or marital status, gender identity or expression, language, national origin, physical and mental ability, political affiliation, race, religion or spiritual belief, sexual orientation, socio-economic status, veteran status, and other characteristics that make our employees unique. We actively cultivate these differences through our employee resource groups (ERGs), employee experiences, perspectives, talents, and approaches to drive innovation in the software and services we provide our customers. We comply with federal and state disability laws and make reasonable accommodations for applicants and employees with disabilities. To request reasonable accommodation in the job application or interview process, please contact accessibility@paylocity.com. This email address is exclusively designated for such requests, aligning with federal and state disability laws. Please do not send resumes to this email address, as they will be removed. The base pay range for this position is $55,000 - $65,000 /yr; however, base pay offered may vary depending on job-related knowledge, skills, and experience. This position is eligible for our variable commission plan and offers a full range of benefits outlined here. This information is provided per the relevant state and local pay transparency laws for the location in which this position will be performed. Base pay information is based on market location. Applicants should apply via www.paylocity.com/careers. Requirements:

Keywords: Paylocity, West Allis , Large Enterprise Sales Development Representative, Sales , Schaumburg, Wisconsin