Chief of Staff, NA Sales

Accountabilities:

• • Serve as a trusted advisor and strategic thought partner to the senior sales executive, supporting decisions around strategy, organizational design, resourcing, and competing priorities.
  • Prepare executive leaders for board meetings, executive leadership reviews, quarterly business reviews, and all-hands meetings by synthesizing data, framing decisions, anticipating questions, and developing compelling narratives.
  • Represent senior leadership in selected meetings, triage competing demands, protect executive focus, and maintain momentum across critical initiatives.
  • Partner with Sales, Marketing, Product, Customer Success, Finance, HR, and Revenue Operations to develop and execute go-to-market strategy across the North American portfolio.
  • Lead annual and quarterly planning activities, including operating plans, territory design, quota setting, capacity planning, budgeting, headcount planning, and hiring priorities.
  • Develop and operationalize new go-to-market motions, including channel and partner strategies, product launches, and vertical-specific initiatives, from initial concept through field adoption.
  • Build and manage a portfolio of strategic cross-functional initiatives, establishing scope, milestones, success measures, ownership, and accountability for execution.
  • Analyze performance across pipeline, conversion, sales attainment, and churn, identifying root causes and translating findings into actionable improvement plans.
  • Own the sales operating rhythm, including forecasting, pipeline reviews, large-deal reviews, monthly business reviews, QBRs, dashboards, KPI reporting, and executive updates.
  • Partner with the leadership team to align priorities, remove organizational friction, support change management, and contribute to engagement, talent reviews, promotions, and organizational planning.
  • Drive disciplined execution across a distributed sales organization while maintaining alignment with broader global sales priorities.

  Requirements:

  • Extensive experience working autonomously across strategy consulting, investment banking, sales or revenue operations, go-to-market strategy, Chief of Staff, business operations, or similarly broad strategic roles.
  • Demonstrated experience supporting and influencing senior sales or revenue executives; B2B SaaS or cybersecurity experience is highly advantageous.
  • Proven ability to lead complex, cross-functional initiatives from strategic definition through execution, with measurable business outcomes.
  • Strong understanding of sales methodologies, pipeline and forecasting management, and revenue operations concepts such as MEDDIC/MEDDPICC, ARR, NRR, and pipeline coverage.
  • Exceptional executive presence and communication skills, with the ability to develop board-level narratives, advise senior stakeholders, and communicate effectively with frontline sales teams.
  • Strong analytical and financial acumen, including the ability to build, evaluate, and challenge financial models, dashboards, operating plans, and executive reporting.
  • High emotional intelligence and organizational awareness, with the ability to build trust, influence stakeholders, and create alignment without relying on formal authority.
  • Structured problem-solving skills and a strong bias toward action, with the flexibility to move between long-term strategic planning and hands-on execution.
  • Strong organizational skills and the ability to manage multiple high-priority initiatives simultaneously in a fast-moving environment.
  • Excellent judgment and discretion when handling confidential information, including organizational changes, employee performance matters, and sensitive strategic or M&A-related topics.
  • Comfortable operating in an ambiguous, rapidly evolving environment while maintaining focus on measurable business outcomes.

  Benefits:

  • Base salary: $184,000–$276,000 USD, with final compensation determined by factors including role level, location, qualifications, experience, and skills.
  • Additional compensation: Eligibility for incentive plans may apply.
  • Benefits: Comprehensive benefits provided in accordance with company policy and applicable local regulations.
  • Work arrangement: Hybrid work schedule for the Lexington, Massachusetts location; remote options are available in Maine, New Hampshire, Rhode Island, and Connecticut.
  • Career exposure: Direct access to senior and executive leadership and the opportunity to influence major commercial and organizational decisions.
  • Strategic impact: Ownership of high-priority initiatives spanning sales strategy, GTM execution, planning, operations, and organizational effectiveness.
  • Inclusive workplace: Commitment to equal employment opportunity and a diverse, respectful, and welcoming working environment.
  • Accessibility support: Workplace and interview accommodations are available for candidates who require them.