Vice President, Sales

Justworks•New York, NY

1d•Hybrid

About The Position

At Justworks, you’ll enjoy a welcoming and casual environment, great benefits, wellness program offerings, company retreats, and the ability to interact with and learn from leaders in the startup community. We work hard and care about our most prized asset - our people. We’re helping businesses get off the ground by enabling them to focus on running their business. We solve HR issues. We’re data-driven and never stop iterating. If you’d like to work in a supportive, entrepreneurial environment, are interested in building something meaningful and having fun while doing it, we’d love to hear from you. We're united by shared goals and shared motivations at Justworks. These are best summed up in our company values, which are reflected in our product and in our team. Justworks is seeking an VP of Sales to drive scalable revenue performance and operational excellence across the go-to-market organization as it enters its next phase of growth. With revenue expectations rising and sales productivity at an inflection point, this leader will play a pivotal role in transforming how Justworks sells, ensuring that processes, culture, and execution evolve in lockstep with the company’s ambitions. The VP of Sales will bring external perspective and hands-on operational rigor to optimize the company’s sales engine for scale. They will lead the current team of ~220, which includes Account Executives (new business), Account Directors (account growth and upsell), Sales Specialists (product-specific overlay), and Sales Development Representatives (pipeline generation and lead qualification), with the autonomy to reshape the organization to meet future needs.

Requirements

Minimum of 10 years of experience in Sales Leadership, ideally with experience in SaaS and a high-velocity sales motion.
Operational Leadership: A proven operator who can architect and implement scalable sales processes and playbooks designed around a high-velocity (~40 day) sales cycle. Experience driving measurable productivity gains across multi-layered sales teams is critical.
Culture Builder: History instilling a strong sense of ownership, accountability, and ambition across the sales force. An understanding of how to bring clarity around what excellence looks like and fosters healthy, values-based competition.
Growth Mindset: History of encouraging continuous learning and development through ongoing coaching, training, and performance feedback. Sees experimentation and failure as opportunities for improvement.
Collaborative Partner: Understanding of how to build a trusted, constructive dialogue with Product and other business units. Translates sales insights into actionable cross-functional plans that drive mutual success.
High-Energy Communicator: Motivates through authenticity, consistency, and transparency. A “say–do” leader who inspires confidence and alignment at every level of the organization.
Proven senior sales leadership experience within a high-growth B2B, SaaS, fintech, or technology-enabled services environment.
Demonstrated success leading large, multi-layered sales organizations (100+ sellers) through periods of significant scale and transformation.
Track record of delivering sustained, predictable revenue growth at scale, including experience managing $300M+ ARR businesses.
Deep understanding of modern go-to-market models spanning new logo acquisition, account expansion, upsell, and specialist overlay motions.
Strong operational orientation with hands-on experience building sales processes, forecasting discipline, and performance management systems.
Ability to attract, develop, and retain top sales leadership talent, with a reputation for building high-performance cultures.
Comfort operating in ambiguity and leading change as the business evolves from growth to scale.
Data-driven decision maker with experience leveraging analytics, CRM platforms, and sales technology to improve outcomes.
Exposure to modern sales methodologies, enablement frameworks, and emerging revenue technologies.
Executive presence and communication skills to influence at the C-suite and Board level.
Experience bringing external best practices and outside perspectives into organizations that are evolving their sales maturity.

Responsibilities

Own and deliver the company’s commercial growth mandate, driving 35%+ ARR growth and scaling revenue from approximately $400M to $800M over three years.
Lead and evolve a sales organization of ~220 professionals across Account Executives, Account Directors, Sales Specialists, and Sales Development, with the authority to reshape structure, roles, and coverage models as the business scales.
Bring external perspectives, modern sales methodologies, and emerging technologies into the organization to continuously evolve how the company sells.
Leverage data, analytics, and sales technology to improve decision-making, consistency, and efficiency across the sales organization.
Build and operationalize a scalable, repeatable sales engine that improves productivity, execution rigor, and forecast accuracy across new business, expansion, and upsell motions.
Drive meaningful improvements in sales productivity through disciplined quota design, capacity planning, territory optimization, ramp expectations, and performance management.
Establish best-in-class sales processes and operating cadences from pipeline generation and qualification through deal execution, renewal, and expansion.
Strengthen pipeline health and coverage across all segments by partnering closely with SDR leadership and ensuring sufficient top-of-funnel generation.
Implement consistent forecasting, inspection, and performance review mechanisms that provide clear visibility into risks, opportunities, and execution gaps.
Partner closely with Marketing, Product, Finance, and other departments to ensure tight GTM alignment and a seamless end-to-end customer lifecycle.
Develop and scale sales leadership talent, building a strong bench of frontline and second-line leaders capable of operating in a high-growth, high-expectations environment.
Set and reinforce a high-performance sales culture that balances accountability, coaching, customer-centricity, and ethical selling practices.
Optimize compensation plans, incentive structures, and performance management frameworks to align behaviors with company growth priorities.
Support enterprise-level deal strategy and execution, including executive sponsorship, complex negotiations, and strategic account engagement as needed.
Ensure effective onboarding and enablement programs that accelerate time-to-productivity and support ongoing skill development.
Continuously evaluate and refine GTM coverage, segmentation, and resource allocation to ensure focus on the highest-value growth opportunities.
Serve as a trusted executive partner to the Chief Revenue Officer and leadership team, contributing to broader company strategy, operating planning, and long-term growth initiatives.