Regional Sales Director

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

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.