Skip to content
GigsGigs

Founding GTM, Strategic Growth

Own the enterprise sales function for Gigs for Work, building regional pipeline, managing complex full-cycle deals, and driving account expansion. The role requires a self-sufficient salesperson with enterprise buyer relationships, strategic commercial judgment, and experience operating in an early-stage environment.

About the job

Responsibilities

  • Build and manage an outbound enterprise pipeline from scratch.
  • Identify and engage senior decision-makers across Security, HR, IT, Procurement, and Finance.
  • Own the full sales cycle from initial contact through signed contract, including procurement and legal processes.
  • Develop long-term customer relationships, identify expansion opportunities, and support retention.
  • Define the ideal customer profile, create buyer-segment outreach playbooks, and develop a regional go-to-market strategy.
  • Partner with Product, Engineering, and Operations to provide market insights and influence the roadmap.

Requirements

  • Proven track record of winning and expanding enterprise accounts.
  • Experience with 3–6 month sales cycles and presenting to VP and C-suite buyers.
  • Existing relationships with enterprise decision-makers in Security, HR, IT, Procurement, and/or Finance.
  • Ability to operate independently without dedicated sales engineering, sales operations, or established playbooks.
  • Strong commercial and strategic judgment, analytical rigor, data fluency, and deal-economics modeling skills.
  • Entrepreneurial mindset and comfort working in early-stage, ambiguous environments.
  • Ability to understand complex products and communicate clear customer value.
  • Interest in enterprise telecom, HR technology, or IT infrastructure.

Compensation & Benefits

  • $130,000–$160,000 annual base salary, plus commission and equity.
  • Stock options.
  • Home office or work-setup stipend.
  • Learning and development budget.
  • Free phone and international data plan.
  • Regular collaboration in company hubs, with flexibility for some remote work and occasional travel.

Skills

Enterprise Sales, Outbound Prospecting, Pipeline Management, Account Expansion, Sales Strategy, Go-to-Market Strategy, Customer Relationship Management, Procurement, Contract Negotiation, Business Case Development, Financial Modeling, Data Analysis, Telecommunications, Hr Technology, It Infrastructure

Dropbox

Dropbox

United States
Account Executive
$130k+/yrRemote4+ YOEAccount Executive

The Account Executive will generate pipeline, manage full-cycle sales, and close net-new mid-market and enterprise customers for Dropbox’s product and emerging AI portfolio. The role requires 4+ years of B2B SaaS sales experience, strong qualification and value-selling skills, and CRM-based pipeline management.

Square

Square

Denver, CO

Mid-Market Account Executive
$130k+/yrOn-site5+ YOEAccount Executive

Own outbound prospecting, consultative selling, negotiations, and closing for complex, multi-product deals with mid-market merchants. Requires at least five years of full-cycle sales experience, proven quota attainment, business development expertise, and Salesforce proficiency.

Square

Square

Sonoma, CA

Territory Account Executive
$129k+/yrOn-site3+ YOEAccount Executive

Own a Sonoma territory through field-based prospecting, product demonstrations, partnerships, and full-cycle sales of Square’s commerce ecosystem. The role requires at least three years of closing experience, field sales expertise, business development skills, and Salesforce proficiency.

Square

Square

United States

Territory Account Executive
$129k+/yrOn-site3+ YOEAccount Executive

Owns a local territory through field-based prospecting, consultative demonstrations, and full-cycle sales of Square’s commerce products. Requires at least three years of closing experience, field sales expertise, and the ability to build pipeline independently.

Square

Square

Everett, WA

Territory Account Executive
$129k+/yrOn-site3+ YOEAccount Executive

Own and grow Square’s Everett territory through in-person prospecting, consultative demos, partnerships, and full-cycle sales of its software and hardware ecosystem. Requires 3+ years of field closing experience, business development skills, reliable transportation, and Salesforce proficiency.