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About the Role

GigSafe is a contractor management platform built for gig and last-mile delivery operations, aiming to help companies pay independent contractors accurately, on time, and in compliance. As an Account Executive, you will own the full sales cycle, selling our onboarding, compliance, and insuretech platform into logistics and blue-collar, deskless industries. You will generate and work your own pipeline, manage complex multi-stakeholder deals, and report to the Head of Revenue.

Responsibilities

Own the complete sales motion: prospect, qualify, discover, demo, negotiate, and close.
Navigate buying committees across organizations, including champions, economic buyers, ops, legal, and finance.
Construct the path to close around the customer's actual needs, timeline, and buying process.
Build the ROI model, cost comparison, or AI-powered calculator needed for complex deals.
Generate pipeline consistently through daily call blocks.
Uncover the actual problem before pitching by understanding needs.
Maintain accurate CRM data for forecasting.
Ensure a smooth transition to the onboarding team post-sale.
Surface deal risks and proposed solutions clearly and early.
Utilize AI to enhance output in research, preparation, follow-up, and drafting.

Requirements

Track record of full-cycle B2B closing with a history of hitting quota, or a proven SDR/BDR ready to advance.
Experience managing complex, multi-stakeholder deals with extended sales cycles.
Experience selling into logistics or blue-collar/deskless industries, understanding buyer behavior.
Experience selling payroll, compliance, and/or insuretech platforms, or adjacent regulated B2B software.
Analytical skills to build financial models and ROI calculations.
Ability to create tailored mutual success plans.
Discipline in maintaining high conversation volume and dedicated call blocks.
Self-directed with strong ownership of commitments and output.
Coachable and able to provide constructive feedback.
Strong written communication skills for framing problems and solutions.
Ability to thrive in an ambiguous, fast-paced startup environment and build processes.
Domain knowledge of workforce compliance, insurance, or payroll in deskless/gig environments is preferred.
Experience as an early Account Executive in a first sales cohort is preferred.
Fluency with modern sales stacks (CRM, sequencing, AI tooling) and leveraging AI is preferred.

Skills

Full-Cycle Selling
Complex Deal Management
Mutual Success Planning
Business Case Development
Pipeline Generation
Discovery
Pipeline Hygiene
Sales Handoffs
Communication
AI Utilization
B2B Sales
CRM
Sequencing
AI Tooling

Location

Remote

Work Type

Full-time

Experience Level

Full-cycle B2B closing experience
SDR/BDR experience ready to step up
Early AE experience

Salary/Compensations

Competitive base salary
Opportunities for performance-based bonuses

Benefits

Comprehensive medical, dental, and vision coverage for employees and dependents
Unlimited PTO plus paid company holidays
Competitive base salary with opportunities for performance-based bonuses
Retirement savings plan (401(k))
Stock options
Paid parental leave

About the Company

GigSafe is a contractor management platform built for gig and last-mile delivery operations.
We are building infrastructure for the future of 1099 work that helps companies pay independent contractors accurately, on time, and in compliance.
We are early in a large market and looking for individuals to build with us.

Equal Opportunity

GigSafe is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other characteristic protected by applicable law.