Regional Sales Director

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

About Portside

Portside is a leading provider of cloud-based software solutions for the global aviation industry. Our platform powers critical operations across business aviation, regional airlines, and aircraft leasing & finance, helping over 1,000 aviation organizations streamline operations, improve decision-making, and operate more efficiently.

About Portside

Portside is a leading provider of cloud-based software solutions for the global aviation industry. Our platform powers critical operations across business aviation, regional airlines, and aircraft leasing & finance, helping over 1,000 aviation organizations streamline operations, improve decision-making, and operate more efficiently.

Backed by leading technology investors Vista Equity Partners and Insight Partners, Portside is entering an exciting phase of growth. We are expanding our platform, investing in AI driven innovation, and building a global team focused on shaping the future of aviation technology.

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.

You will partner closely with Marketing, Enablement, Product, and Customer Success to turn market opportunity into revenue. The ideal candidate has led a quota-carrying team in B2B SaaS, is comfortable selling to senior decision-makers, and thrives in a fast-scaling, high-autonomy environment.

Key Responsibilities

• Drive your team's revenue results across new business and expansion, and report on performance, forecast accuracy, and pipeline health to the CRO.
• Lead, coach, and develop your Sales Executives with clear goals, weekly pipeline reviews, regular call coaching, and individual development plans.
• Recruit, onboard, and ramp new Sales Executives as the team grows, working with Enablement on onboarding, training, and certification.
• Build and execute the go-to-market plan for your region, including territory design, target account strategy, and segmentation across business aviation, regional airlines, and aircraft leasing & finance.
• Drive disciplined execution through a consistent sales methodology: qualification, deal strategy, negotiation, close, and CRM hygiene. Set the forecasting process and performance metrics, and scale them as the team grows.
• Stay in the deals that matter. Lead strategic, multi-stakeholder opportunities and build executive-level relationships with customers.
• Partner with Marketing and the BDR team to align campaigns, events, and outbound prospecting with your target accounts.
• Work with Product and Customer Success on smooth handoffs, adoption, renewals, and expansion as customers move to the right-fit Portside products, and bring customer feedback into the roadmap.
• Use AI-enabled tools and workflows to improve team productivity, prospecting, and deal insight, and help articulate Portside's AI-driven product story to customers.
• Keep deep knowledge of the aviation market, competitors, and customer needs, and represent Portside at industry events and customer meetings.

Qualifications

• 7-10+ years of B2B SaaS sales experience, including 3+ years managing a team of quota-carrying sales executives or account executives
• Proven track record of meeting or exceeding revenue targets in enterprise or mid-market software sales, including complex, multi-stakeholder deals
• Experience building or scaling a sales team, including hiring, coaching, and performance management
• Strong forecasting, pipeline management, and sales process disciplineComfortable moving between strategic leadership and deal support, including joining customer calls, guiding negotiations, and helping deals through to close.
• Experience with a CRM such as Salesforce or HubSpot and a data-driven approach to managing performance
• Excellent written and verbal communication skills, with the ability to engage senior customer executives and represent the team to company leadership
• Willingness to travel as needed to meet customers and attend industry events
• Bachelor's degree or equivalent work experience (preferred)

What We Offer

• Competitive base salary
• Fully remote work
• Generous time off policy
• Health, dental, and vision insurance
• Opportunities for professional development and career advancement.
• Dynamic, collaborative, and fast-growing work environment.

Portside is an equal-opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.