Vice President of Sales

About This Role

This role involves driving scalable revenue performance and operational excellence across the go-to-market organization as the company enters its next phase of growth. The Vice President of Sales will play a pivotal role in transforming how the company sells, ensuring that processes, culture, and execution evolve in lockstep with its ambitions. They will bring external perspective and hands-on operational rigor to optimize the company’s sales engine for scale.

Responsibilities

• Drive scalable revenue performance and operational excellence across the go-to-market organization
• Transform how the company sells, ensuring processes, culture, and execution evolve with company ambitions
• Optimize the company’s sales engine for scale by bringing external perspective and hands-on operational rigor
• Lead the current team of approximately 220 professionals, including Account Executives, Account Directors, Sales Specialists, and Sales Development Representatives
• Reshape the sales organization to meet future needs with autonomy
• Own and deliver the company’s commercial growth mandate, driving 35%+ ARR growth
• Scale revenue from approximately $400M to $800M over three years
• Evolve a sales organization of approximately 220 professionals across various roles, with 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

Requirements

• Minimum of 10 years of experience in Sales Leadership, ideally with experience in SaaS and a high-velocity sales motion
• Proven operational leadership to architect and implement scalable sales processes and playbooks designed around a high-velocity (approximately 40 day) sales cycle
• Experience driving measurable productivity gains across multi-layered sales teams
• History of instilling a strong sense of ownership, accountability, and ambition across the sales force
• Understanding of how to bring clarity around what excellence looks like and fosters healthy, values-based competition
• History of encouraging continuous learning and development through ongoing coaching, training, and performance feedback
• Ability to see experimentation and failure as opportunities for improvement
• Understanding of how to build a trusted, constructive dialogue with Product and other business units
• Ability to translate sales insights into actionable cross-functional plans that drive mutual success
• High-energy communicator who motivates through authenticity, consistency, and transparency
• 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
• Good judgment, exercising 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, thorough, accurate, organized, and productive; seeks to understand both the cause and effect of a situation

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 overall wellness on topics like nutrition, budgeting, and mindfulness
• Equity included in all offers, with opportunities to earn more over time with promotions and tenure
• Extensive learning and development opportunities through workshops, ExecOnline, Udemy, and BetterUp coaching
• Engineering Apprenticeship program that supports internal movement and growth

Important Details

• Team: approximately 220 professionals, including Account Executives (new business), Account Directors (account growth and upsell), Sales Specialists (product-specific overlay), and Sales Development Representatives (pipeline generation and lead qualification)