Director CPA Field

PAYLOCITY CORPORATION•Town of Pittsford, NY

About The Position

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. The Director, CPA Field role is a second-line sales leader responsible for driving sustained revenue growth by leading, coaching, and developing front-line sales managers and their teams within an assigned region or vertical. This role owns sales execution at scale, translating corporate strategy into actionable plans, building leadership capability, and ensuring consistent performance across multiple sales teams. This position requires a proven B2B sales leader with strong business acumen, deep people leadership experience, and a track record of developing high-performing sales organizations. This role operates as a strategic partner to senior leadership while remaining closely connected to the field.

Requirements

Bachelor’s degree in Business, Marketing, or a related field preferred.
7+ years of progressive experience in B2B sales or business operations.
3+ years of experience leading sales leaders (manager-of-managers experience strongly preferred).
Experience managing HCM Account Executives and selling into large, complex organizations.
Demonstrated success driving revenue through multiple teams and leaders.
Strong understanding of payroll, HR, time and attendance, and HCM solutions.
Proficiency with CRM platforms (e.g., Salesforce, HubSpot) and sales analytics.
Proven ability to lead in a fast-paced, evolving, and virtual environment.
Willingness and ability to travel as needed.

Responsibilities

Lead, coach, and develop Sales Managers, ensuring consistent execution of sales strategy and leadership standards across teams.
Establish clear expectations for manager effectiveness, including coaching quality, pipeline discipline, forecasting accuracy, and talent development.
Drive leadership capability by mentoring managers on performance management, coaching methodologies, and employee engagement.
Own succession planning and talent readiness for the sales organization; identify high-potential talent and develop future leaders.
Partner with Sales Enablement and HR to ensure consistent onboarding, training, and leadership development programs.
Reinforce and scale the Paylocity sales process through manager accountability and inspection rhythms.
Lead organizational change initiatives, ensuring adoption of new tools, processes, and go-to-market strategies.
Translate company revenue goals into regional and team-level operating plans.
Own execution of sales strategy across multiple teams to achieve revenue, growth, and retention targets.
Partner with senior leadership to define territory design, coverage models, and capacity planning.
Ensure strong pipeline health and conversion performance through manager-led inspection and coaching.
Drive consistent deal strategy and pricing discipline on large, complex, or strategic opportunities.
Identify systemic performance gaps and implement scalable solutions to improve productivity and results.
Own regional/vertical forecasting accuracy and pipeline governance.
Analyze sales performance trends, leading indicators, and market dynamics to inform business decisions.
Conduct regular business reviews with Sales Managers focused on results, risks, and corrective actions.
Provide clear, data-driven updates to senior leadership on performance, risks, and growth opportunities.
Ensure alignment between bookings, revenue, and customer outcomes.
Serve as executive sponsor for key accounts and strategic opportunities.
Act as an escalation point for complex customer situations, ensuring alignment between sales, customer success, and product teams.
Promote a customer-centric, value-based selling culture across the organization.
Stay informed on industry trends, competitor positioning, and evolving customer needs to inform sales strategy.
Partner closely with Marketing, Product, Customer Success, Finance, and HR to align sales execution with broader business objectives.
Provide structured feedback on product gaps, competitive insights, and customer experience trends.
Influence go-to-market planning, campaign strategy, and enablement priorities.
Partner with Talent Acquisition to hire and onboard high-caliber sales managers and sellers.
Set and reinforce performance standards and accountability across teams.
Lead performance calibration, compensation understanding, and incentive effectiveness discussions.
Foster an inclusive, high-performance culture grounded in transparency, ownership, and continuous improvement.