Remote Regional Sales Director - Aviation SaaS

Rippling (Netherlands); Nashville (TN); Remote; USD 180,000 - 260,000; Full time

Benefits offered by this job

Fully remote

Generous time off

Health, dental & vision insurance

Professional development

Dynamic environment

Job summary

Portside is seeking a Regional Sales Director to lead 8-10 Sales Executives and drive revenue across business aviation, regional airlines, and aircraft leasing & finance. You will coach teams through complex enterprise cycles, engage senior decision-makers, and own regional performance in a fast-scaling, high-autonomy environment.

You will partner with Marketing, Enablement, Product, and Customer Success to turn market opportunities into revenue.

Qualifications

• 7–10+ years of B2B SaaS sales experience with a quota-carrying team leadership background
• Proven track record of meeting or exceeding revenue targets in enterprise or mid-market software sales
• Experience building or scaling a sales team, including hiring, coaching, and performance management
• Strong forecasting, pipeline management, and sales process discipline
• Proven ability to engage senior customer executives and manage multi-stakeholder deals

Responsibilities

• Drive team revenue across new business and expansion, with forecasting and pipeline health reporting to the CRO
• Lead, coach, and develop Sales Executives with goals, pipeline reviews, and development plans
• Recruit, onboard, and ramp new Sales Executives as the team grows
• Build and execute go-to-market plans for the region, including territory design and segmentation
• Maintain disciplined execution with qualification, strategy, negotiation, close, and CRM hygiene
• Lead strategic, multi-stakeholder opportunities and build executive relationships
• Collaborate with Marketing and BDR to align campaigns with target accounts
• Coordinate with Product and Customer Success for smooth handoffs, adoption, renewals, and expansion
• Leverage AI-enabled tools to boost productivity and articulate AI-driven product storytelling to customers

Skills

B2B SaaS sales

Team leadership

Enterprise deals

Forecasting

CRM (Salesforce/HubSpot)

Strategic selling

Communication

Travel willingness

Education

Bachelor's degree or equivalent

Tools

Salesforce

HubSpot

Job description

Portside is seeking a Regional Sales Director to lead 8-10 Sales Executives and drive revenue across business aviation, regional airlines, and aircraft leasing & finance. You will coach teams through complex enterprise cycles, engage senior decision-makers, and own regional performance in a fast-scaling, high-autonomy environment.

You will partner with Marketing, Enablement, Product, and Customer Success to turn market opportunities into revenue.