Vice President of Sales, Justworks
$460-530k
OTE
$230-265k
BASE
Expert level
New York
Business operations platform
Job no longer available
Business operations platform
1001+ employees
FintechB2BEnterpriseHRCompliancePaymentsSaaS
Job no longer available
$460-530k
OTE
$230-265k
BASE
Expert level
New York
1001+ employees
FintechB2BEnterpriseHRCompliancePaymentsSaaS
Company mission
To help entrepreneurs and businesses grow with confidence.
Role
Who you are
- 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
What the job involves
- 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
- 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
- As a Vice President of Sales, how results are achieved is paramount for your success and result in our success as an organization. In this role, your foundational knowledge, skills, abilities, and personal attributes are anchored in the following competencies:
- Good judgment - the exercise of critical thinking, analyzing and assessing problems and implications, identifying patterns, making connections of underlying issues, understanding risks and developing mitigation strategies, and taking ownership of the outcome
- Detail-oriented - exercises extreme attention to detail; is thorough, accurate, organized, and productive; seeks to understand both the cause and effect of a situation
- Foundational sales knowledge - the specific set of sales skills (prospecting, cold calling, nurturing, engaging, presenting, negotiating, closing, etc.) and knowledge (product, markets, trends, business, etc) a person possesses to enact the exchange of value between a buyer and the vendor
- Results-driven - consistently achieves results, even under difficult circumstances
- Clear communication - the ability to articulate thoughts and express ideas effectively using oral, written, visual and non-verbal communication skills, as well as listening skills to gain understanding
Our take
Justworks operates in an increasingly crowded space of all-in-one business operation suites, that include tools like human resources, payroll, employee management, benefits, and others that businesses critically need to operate as they scale.
Globally, human resource management has become an extremely fertile field, creating great opportunity for Justworks to continue to grow. The company is regarded as a market leader, but does see competition in the shape of Paychex Flex, Rippling, Paylocity, and TriNet, among others.
Justworks' solutions have proven extremely popular with SMEs, and this has not gone unnoticed by investors - with the company picking up considerable amounts of funding. The company is known to have sights on going public, though these were delayed somewhat by market conditions. That said, it has continued to expand operations and acquired Via in 2024, signalling that its going strong.
Steph
Company Specialist at Welcome to the Jungle
Insights
Top investors
24% employee growth in 12 months
Company
Funding (last 2 of 7 rounds)
Nov 2023
$16.9m
LATE VC
Jan 2020
$50m
SERIES E
Total funding: $159.9m
Company benefits
- Paid volunteer work
- Paid parental leave
- Work from home opportunities
- Medical, dental, and vision insurance, plus access to One Medical, Kindbody, and Teladoc
- Premium access to Headspace, ClassPass stipends, and webinars to support your overall wellness on topics like nutrition, budgeting, mindfulness, and more
- All Justworks offers include equity, and Justworkers can continue to earn more over time with promotions and tenure
- Extensive learning & development opportunities through workshops, ExecOnline, Udemy, and BetterUp coaching
- Apprenticeship program that supports internal movement and growth
Company HQ
Fulton Ferry District, NY
Leadership
Isaac Oates
(Founder & Director)Experience as a Senior Product Manager at Amazon before founding Adtuitive and serving as COO for a year. Left this position to spend 3 years as a VP at Etsy, before founding Justworks.
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