[Hiring] Regional Sales Director @Portside

Role 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.

• Lead 8-10 Sales Executives and help hire and ramp the team as it grows.
• Coach the team through complex enterprise sales cycles and step into the most strategic deals yourself.
• 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.

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 discipline.
• Comfortable 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).

Requirements

• 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.
• Use AI-enabled tools and workflows to improve team productivity, prospecting, and deal insight.
• Keep deep knowledge of the aviation market, competitors, and customer needs, and represent Portside at industry events and customer meetings.

Benefits

• 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.