Remote Regional Sales Director - Lead Enterprise SaaS

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

Benefits offered by this job

Fully remote work

Competitive base salary

Generous time off

Health, dental, and vision insurance

Professional development

Dynamic, fast-growing environment

Job summary

Portside is seeking a Regional Sales Director to lead a team of 8–10 Sales Executives and drive new business across business aviation, regional airlines, and leasing & finance. You will report to the CRO and own your team's number.

You will recruit, coach, and ramp the team, while engaging in strategic deals yourself. Collaboration with Marketing, Enablement, Product, and Customer Success is key to turning opportunity into revenue.

Qualifications

• 7-10+ years of B2B SaaS sales experience, including 3+ years managing a quota-carrying team.
• Proven track record of meeting/reaching revenue targets in enterprise or mid-market software sales.
• Experience building or scaling a sales team with coaching and performance management.
• Strong forecasting, pipeline management, and sales process discipline.
• Experience with a CRM such as Salesforce or HubSpot.
• Excellent written and verbal communication, engaging senior executives.
• Willingness to travel as needed to meet customers/events.
• Bachelor's degree or equivalent work experience (preferred).

Responsibilities

• Drive revenue for new business and expansion across target segments.
• Lead, coach, and develop Sales Executives with clear goals and pipeline reviews.
• Recruit, onboard, and ramp new Sales Executives as the team grows.
• Build and execute the go-to-market plan for your region.
• Maintain disciplined sales execution: qualification, strategy, negotiation, close, CRM hygiene.
• Lead strategic, multi-stakeholder opportunities and build executive relationships.
• Partner with Marketing and BDR to align campaigns with target accounts.
• Collaborate with Product/CS on handoffs, adoption, renewals, and expansion.
• Leverage AI tools to boost productivity and articulate Portside's AI story.
• Maintain deep knowledge of aviation market, competitors, and customer needs.

Skills

B2B SaaS sales

Team leadership

Forecasting

CRM proficiency

Education

Bachelor's degree or equivalent

Tools

Salesforce

HubSpot

Job description

Portside is seeking a Regional Sales Director to lead a team of 8–10 Sales Executives and drive new business across business aviation, regional airlines, and leasing & finance. You will report to the CRO and own your team's number.

You will recruit, coach, and ramp the team, while engaging in strategic deals yourself. Collaboration with Marketing, Enablement, Product, and Customer Success is key to turning opportunity into revenue.