Chief of Staff to the Head of Sales

Role Overview

Chief of Staff to the Head of Sales at Assured, acting as a force multiplier for sales leadership across go-to-market execution. This role sits at the intersection of sales strategy and day-to-day operations, supporting the sales leader in shaping decisions, operating rhythms, deals, and accountability.

Responsibilities

• Serve as right-hand to the Head of Sales
  • Act as a trusted thought partner/proxy
  • Manage the strategic agenda, prepare for internal/customer meetings, and ensure priorities translate into action
• Own sales operating cadence
  • Run pipeline reviews, forecast calls, QBRs, staff meetings, and sales off-sites
  • Ensure meetings are well-prepared, decision-oriented, and followed through
• Drive pipeline visibility & forecasting
  • Build/maintain reporting, dashboards, and analysis for pipeline health and forecast accuracy
• Own sales enablement
  • Create decks, one-pagers, and narratives used in key customer meetings so reps have what they need to win
• Lead cross-functional coordination
  • Align with Marketing, Customer Engineering, Product, and Finance on handoffs, launches, and shared GTM priorities
• Structure complex problems
  • Use analytical frameworks for segmentation, territory strategy, pricing inputs, and win/loss analysis
• Support hiring and onboarding
  • Partner on recruiting, interviewing, and onboarding across the sales organization

Requirements

• Thrives in ambiguity and can bring structure to chaos
• Strong execution and follow-through; able to shift between strategic and tactical work

Nice to Haves

• Experience working within or alongside a Forward Deployed Team (FDT) / forward-deployed discovery-to-production GTM motion (supporting rather than owning it)