Chief of Staff

The Chief of Staff is a high-visibility leadership role responsible for the operational success of the VP, General Manager’s organization. Acting as a strategic partner, you will ensure the business operates at peak velocity by driving key initiatives, improving organizational effectiveness, and aligning teams around strategic priorities. You will translate high-level goals into clear execution plans across the business, providing clarity in a fast-paced, complex environment.

This role is designed for a seasoned operator who excels at driving accountability among senior leaders and building the systems necessary to scale a SaaS business. You will identify operational gaps, mitigate risks before they impact the bottom line, and act as an extension of leadership—prioritizing, executing, and communicating critical projects to enable the executive team to operate at maximum efficiency.

** Please note that this opportunity is located in New York, NY, and requires this hire to work from our office 4 days a week. **

• Drive the Operating Cadence: Design and manage the GM’s leadership meetings, QBRs, and planning cycles to ensure the team is aligned and hitting KPIs.
• Force Execution: Partner with Product, Sales, CS, and Engineering leaders to unblock projects and hold senior stakeholders accountable for deliverables.
• Prioritize Ruthlessly: Act as a surrogate for the GM in high-level meetings, surfacing critical risks early and filtering out noise to focus the organization on top priorities.
• Build Systems & Visibility: Develop dashboards and reporting structures that provide real-time clarity on business health and cross-functional performance.
• Lead Special Projects: Own high-impact, ambiguous initiatives that don’t have a natural home (e.g., market expansion research, internal restructuring, or post-launch retrospectives).
• Facilitate High-Stakes Decisions: Prepare briefing materials, research, and frameworks that enable the GM to make fast, informed decisions.
• Strategic Execution & Cross-Functional Leadership
  • Partner with executive leadership to define, prioritize, and drive the company’s most critical initiatives
  • Help formulate and drive longer term business strategy as well as short term strategic planning and alignment with FP&A processes
  • Lead cross-functional execution across Product, Sales, Customer Success, and Engineering to ensure alignment and delivery
  • Proactively identify risks, surface issues early, and drive timely decision-making
• Operational Excellence & Systems Thinking
  • Build and implement operating cadences, dashboards, and tracking mechanisms to measure progress against key priorities
  • Establish structure and clarity in ambiguous or evolving environments
  • Continuously identify opportunities to improve organizational effectiveness and execution
• Executive Partnership & Accountability
  • Act as a trusted advisor and thought partner to senior leadership
  • Help prioritize competing demands and ensure focus on the highest-impact work
  • Hold executive leaders accountable for commitments, deliverables, and outcomes
• Communication & Alignment
  • Drive alignment across the leadership team through clear communication, structured updates, and effective meeting cadences
  • Prepare executive-level materials, including presentations, briefings, and business reviews
  • Facilitate leadership meetings, ensuring clear agendas, decisions, and follow-ups
• Special Projects
  • Lead high-impact, often ambiguous initiatives from concept through execution
  • Conduct analysis and develop recommendations to support strategic decisions

To Thrive in This Role, You’ll Need:

• 5+ years experience in high-growth SaaS operator roles (e.g., Biz Ops, Product Ops, RevOps, or a prior CoS/Founder role) OR deep domain expertise in SaaS business models and operations gained from consulting and private/growth equity backgrounds.
• Executive Presence: The confidence to challenge senior leaders and the diplomacy to drive consensus across competing departments.
• Clarity from Chaos: A proven ability to walk into an ambiguous environment and build the structure, processes, and documentation needed to scale.
• Deep SaaS Literacy: You understand the operational levers of a SaaS P&L—churn, NRR, CAC, and product velocity as well as financial levers - bookings/sales targets achivement, financial analysis, unit economics, financial performance ratios
• Strong Judgment: You know when to handle a situation yourself and when to escalate to the GM.

What VTS Values & How We Show It

• Strive for Excellence - We know your potential is unlimited. Take advantage of our executive coaches and our training and career development programs available to all employees! 
• Be Customer Obsessed - We’re employee obsessed too! VTS offers competitive compensation, comprehensive health benefits (including dental and vision), pre-tax commuter benefits, and a 401(k) plan. Not to mention the fun stuff - quarterly happy hours, wellness events, clubs, and team lunches! 
• Be Curious - Benefit from a culture that promotes new learning. VTS offers an education stipend to all employees! 
• Move as One - We work in an open floor plan to promote cross-functional collaboration. 
• Take Ownership - Be an owner of the company you’re building with our equity packages. 
• Appreciate the Difference - VTS embraces and celebrates diversity. We understand the importance of a strong work-life balance. We offer a flexible PTO policy, generous family leave program, and more!

Privacy Policy