Full-time Head of Sales, Portside

01Job 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.

02Key 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.

03Qualifications

• 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)

04What We Offer

Competitive base salary

05Fully remote work

Generous time off policy

06Health, 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.