Chief of Staff

Growth Signals•Sarasota, FL

About The Position

This role serves as a strategic partner to the CEO, focusing on translating priorities into actionable workstreams, driving the weekly operating cadence, and preparing executive materials. The Chief of Staff will also be responsible for GTM Operations & Business Rhythm, Deal Desk, Pipeline, and Reporting, Cross-Functional Coordination, and Special Projects & Strategic Initiatives. The ideal candidate will have experience in early-stage or high-growth environments, a strong understanding of go-to-market functions, and the ability to bring structure to ambiguity and drive execution across multiple stakeholders.

Requirements

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

Nice To Haves

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

Responsibilities

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
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
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
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
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