Head of Enterprise Sales Development

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.

Position Overview

Head of Enterprise Sales Development is a pivotal second-line leadership role overseeing a team of SDR Managers and their respective teams, driving pipeline growth through strategic outbound efforts. Expertise in sales development best practices, team leadership, and the HCM landscape will be instrumental in crafting a scalable and results-oriented outbound sales strategy. This position works in close collaboration with Sales, Marketing, and Product teams to refine messaging, target the right prospects, and generate qualified leads that progress into revenue generating opportunities.

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

Leadership & Strategy

• Lead and develop a team of 4 front-line leaders and 31 Sales Development Reps (SDRs), focusing on recruitment, training, coaching, and performance management to drive exceptional results.

• Develop and implement innovative outbound sales strategies to accelerate revenue growth and exceed performance targets.

• Identify and implement ongoing improvements in the areas of process, efficiency, and productivity.

• Track key sales development metrics, analyze team performance against established goals, and provide regular, insightful reports to senior management.

• Foster a high-energy, collaborative, and results-oriented team culture focused on motivation, accountability, and continuous improvement.

Coaching & Performance Optimization

• Mentor the Sales Development team to effectively apply company strategies, aligning individual goals with team objectives to foster a high-performance culture.

• Continuously enhance cold-calling, prospecting, and email outreach techniques to improve conversion rates and pipeline impact.

• Provide constructive feedback to managers during quarterly business reviews, focusing on team results, successes, and actionable plans for improvement.

Collaboration

• Collaborate with the Marketing team to craft impactful outreach campaigns and messaging that resonate with target customer profiles.

• Stay up to date with industry trends, challenges, and innovations in the HCM space to refine outreach strategies and messaging.

• Lead regular weekly and monthly team meetings to review progress, share best practices, and establish clear action plans for success.

Education and Experience

• 8+ years of experience in sales development, inside sales, or a similar role, preferably in SaaS or B2B technology.

• 5+ years of leadership experience managing SDRs or inside sales teams.

• 4+ years of experience as a Sales Development Manager and 2+ years of leading SDR managers.

• Proven success building outbound teams of 20+ reps and 2+ managers with a track record of exceeding pipeline goals.

• Experience in SaaS, B2B technology, or the Human Capital Management (HCM) space preferred.

• Expertise in optimizing outbound sales development processes, from lead generation to qualification, with a track record of implementing best practices that drive growth.

• Proven ability to coach, mentor, and develop SDR managers and teams, including recruiting, onboarding, and providing ongoing training to ensure team members meet their goals and grow professionally.

• Skilled in developing and analyzing performance metrics and KPIs, with experience using data to drive decision making and continuous improvement.

• Proficient in Sales Development tools such as Salesforce, SalesLoft, ZoomInfo, Sales Navigator and Nooks, with deep understanding of their capabilities.

• Ability to adapt to changing market conditions and evolving business needs, with a proactive approach to embracing and driving innovation.

• Role requires close partnership with aligned Sales leadership.

• Excellent communication, negotiation, and presentation skills.

• Bachelor's degree in business, marketing, or related field.

• Consistent in-office presence with flexibility for occasional remote work.

Physical requirements

• Ability to sit for extended periods: The role requires sitting at a desk or workstation for long periods, typically 7-8 hours a day.

• Use of computer and phone systems: The employee must be able to operate a computer, use phone systems, and type. This includes using multiple software programs and inquiries simultaneously.

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 View email address on click.appcast.io. 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. This position is eligible for our variable commission plan, annual bonus, and restricted stock until grant based on individual performance, in addition to a base pay range of $130,000-145,000/yr. However, base pay offered may vary depending on job-related knowledge, skills, and experience. This position is eligible for an annual bonus and restricted stock unit grant based on individual performance in addition to 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

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