Chief of Staff

Growth Signals

• $120K — $150K *
Sarasota, FL 34232In-Person
Business Services
5 - 7 years of experience
1 week ago
Job Overview by Ladders

Qualifications

  • 6-10+ years in business operations or similar roles
  • Experience in fast-paced, high-growth environments
  • Strong understanding of go-to-market functions
  • Experience with pipeline management and forecasting
  • Ability to structure ambiguous projects and drive execution
  • Excellent communication and executive-level writing skills
  • Highly organized and detail-oriented

Responsibilities

  • Partner with the CEO to translate strategic priorities into actionable tasks
  • Drive the weekly operational cadence and decision tracking
  • Prepare executive materials and key business summaries
  • Support the execution of the company’s go-to-market strategy
  • Maintain visibility into pipeline health and customer journey bottlenecks
  • Own the deal desk process and pipeline management
  • Coordinate execution across multiple teams, ensuring alignment

Benefits

  • Collaborative work environment with a direct line to the CEO
  • Opportunity to impact strategic decisions and company growth
  • Exposure to various departments and operational challenges
  • Develop skills in high-visibility projects and initiatives
  • Flexible working environment accommodating fast-paced changes
Full Job Description
What You'll Do:

  • Partner directly with the CEO to translate priorities into actionable workstreams, timelines, and ownership
  • Drive the weekly operating cadence (leadership meetings, priorities, follow-ups, decision tracking)
  • Prepare executive materials including leadership updates, board prep, and key business summaries
  • Ensure alignment and accountability across leadership team initiatives

GTM Operations & Business Rhythm

  • Support the structure and execution of the company's go-to-market motion (Sales, Partnerships, Marketing, Customer Success)
  • Create and maintain visibility into pipeline health, funnel progression, and GTM activity
  • Identify bottlenecks in the customer journey and help coordinate solutions across teams
  • Establish simple, repeatable operating systems that improve execution without slowing the business down

Deal Desk, Pipeline, and Reporting (Core Ownership)

  • Own the deal desk process, including deal structuring support, internal coordination, and approval workflows
  • Serve as the central point of coordination for complex or strategic deals
  • Own pipeline management discipline, including forecasting inputs, stage definitions, and consistency of CRM usage
  • Build and maintain clear, executive-ready reporting on pipeline, conversion, and GTM performance
  • Ensure leadership has an accurate, real-time view of business health and forward-looking indicators

Cross-Functional Coordination

  • Drive execution across Sales, Product, Partnerships, and Customer teams
  • Ensure clear handoffs and alignment across customer lifecycle stages
  • Support partner and alliance initiatives through coordination, follow-through, and tracking
  • Step into ambiguous, high-priority projects that don't clearly "sit" within a single function

Special Projects & Strategic Initiatives

  • Lead high-impact projects from concept through execution
  • Bring structure to new initiatives (clear goals, owners, timelines, and success criteria)
  • Help the company operationalize new ideas without overbuilding process too early
  • Act as a force multiplier for the CEO and leadership team

Required Qualifications

  • 6-10+ years of experience in business operations, GTM operations, consulting, chief of staff, or similar operating roles
  • Experience in early-stage or high-growth environments where priorities shift quickly
  • Strong understanding of go-to-market functions (sales, partnerships, customer success, marketing)
  • Experience supporting or managing pipeline, deal desk, forecasting inputs, or GTM reporting
  • Proven ability to bring structure to ambiguity and drive execution across multiple stakeholders
  • Strong communication skills, including executive-level writing and synthesis
  • Highly organized, detail-oriented, and able to manage multiple priorities simultaneously
  • High ownership mindset with strong judgment and discretion

Preferred Qualifications

  • Experience working closely with founders, CEOs, or executive teams
  • Background in B2B SaaS, enterprise software, or consulting environments
  • Experience with CRM systems, reporting tools, and pipeline tracking frameworks
  • Exposure to partner ecosystems, alliances, or consulting-style revenue motions
  • Experience building lightweight systems from scratch in fast-moving environments
* Ladders Estimates

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