Regional Sales Director - Remote & AI-Driven Growth

Portside; Austin (TX); Remote; USD 180,000 - 280,000; Full time

Benefits offered by this job

Competitive base salary

Fully remote work

Generous time off policy

Health, dental, and vision insurance

Opportunities for professional dev and

career advancement.

Dynamic, collaborative, fast-growing

Job summary

Portside is seeking a Regional Sales Director to lead a team of Sales Executives and drive new business and expansion revenue across business aviation, regional airlines, and aircraft leasing & finance. You will report to the Chief Revenue Officer and own your team's number.

You will lead 8-10 Sales Executives today and help hire and ramp the team as it grows. You will coach them through complex enterprise sales cycles and step into the most strategic deals yourself.

Qualifications

• 7–10+ years of B2B SaaS sales experience.
• 3+ years of leading quota-carrying teams.
• Proven ability to meet revenue targets in enterprise or mid-market deals.
• Experience building and scaling a sales team.
• Strong forecasting and data-driven performance management.
• CRM experience (Salesforce or HubSpot) and data-driven approach.
• Excellent written and verbal communication with executives.
• Willingness to travel to meet customers and events.
• Bachelor's degree or equivalent work experience (preferred).

Responsibilities

• Drive team revenue across new business and expansion; report on forecast and pipeline health.
• Lead, coach, and develop Sales Executives with clear goals and pipeline reviews.
• Recruit, onboard, and ramp new Sales Executives.
• Build go-to-market plan for your region across business aviation segments.
• Ensure disciplined sales execution including qualification, deal strategy, negotiation, and close.
• Maintain executive relationships with customers on strategic deals.
• Collaborate with Marketing and BDR to align campaigns with target accounts.
• Coordinate with Product and Customer Success on handoffs, renewals, and expansion.
• Leverage AI-enabled tools to improve productivity and articulate Portside's AI-driven product story.
• Maintain deep knowledge of aviation market and represent Portside at events.

Skills

B2B SaaS sales

Team leadership

Forecasting & pipeline management

CRM (Salesforce or HubSpot)

Executive relationship building

Education

Bachelor's degree or equivalent

Tools

Salesforce

Job description

Portside is seeking a Regional Sales Director to lead a team of Sales Executives and drive new business and expansion revenue across business aviation, regional airlines, and aircraft leasing & finance. You will report to the Chief Revenue Officer and own your team's number.

You will lead 8-10 Sales Executives today and help hire and ramp the team as it grows. You will coach them through complex enterprise sales cycles and step into the most strategic deals yourself.