Federal DoW Regional Sales Director (Remote)

Jackalope Digital LLC; Northern (KY); Hybrid; USD 148,000 - 248,000; Full time

Benefits offered by this job

Flexible PTO

Equity compensation

Employee stock purchase plan

Growth and development fund

Parental leave

Job summary

GitLab is seeking a Director of Regional Sales to lead the DoW federal field team and drive new and expansion revenue across large, multi-year contracts. You’ll own strategy, coach Account Executives, and navigate complex procurement motions with distributors and partners in a remote, high-performance environment.

Collaborate across Renewals, CS, Marketing, Product, and federal ecosystems to align go-to-market plans, ensure FedRAMP-aligned offerings, and accelerate land-and-expand growth with

Qualifications

• Experience building and leading regional, field-based sales teams in open source software, DevOps, or related enterprise technology environments.
• Background in process- and data-driven sales operations with Salesforce and other CRM/marketing automation tools.
• Experience selling in regulated or compliance-driven environments (e.g., FedRAMP) or ability to ramp quickly in regulated markets.
• Demonstrated success selling complex enterprise deals into large public sector accounts with long sales cycles.
• Familiarity with MEDDPICC or similar frameworks for pipeline generation and forecasting.
• Ability to hire, coach, and develop sales talent in a high-performance, inclusive culture.
• Proven track record managing C-level and senior stakeholder negotiations in federated organizations.

Responsibilities

• Lead, recruit, hire, and coach a high-performing team of Account Executives covering DoW to achieve regional revenue targets.
• Drive strategy and execution for new business and expansion, building and converting pipeline across DoW accounts.
• Own regional forecasting, pipeline health, and deal qualification to improve win rates and shorten cycles.
• Navigate complex federal procurement motions with distributors and partners to secure multi-year contracts and expansions.
• Shape go-to-market strategies for FedRAMP offerings and drive platform adoption in priority accounts.
• Collaborate with Renewals, CS, Marketing, Product, and ecosystem partners to align plans and campaigns.
• Lead land-and-expand motions in large federated organizations for ongoing growth.
• Engage in field activities and travel to support key meetings and executive engagements.

Skills

Regional leadership

Open source

DevOps

Sales operations

Salesforce

CRM tools

Marketing automation

FedRAMP

Regulated markets

Executive engagement

MEDDPICC

Tools

Salesforce

MEDDPICC

Job description

GitLab is seeking a Director of Regional Sales to lead the DoW federal field team and drive new and expansion revenue across large, multi-year contracts. You’ll own strategy, coach Account Executives, and navigate complex procurement motions with distributors and partners in a remote, high-performance environment.

Collaborate across Renewals, CS, Marketing, Product, and federal ecosystems to align go-to-market plans, ensure FedRAMP-aligned offerings, and accelerate land-and-expand growth with