Sales Director, TrustFlight

• Are you a strategic sales leader who thrives on clarity, alignment, and momentum? Do you get energized by transforming fragmented efforts into a focused, high-performing revenue engine—and taking bold bets on new markets?
• This is a senior-level role for someone with deep experience in B2B SaaS sales, likely with 7+ high performing years in sales and several years in team leadership or director-level positions
• Proven Scale Experience: You have demonstrated success scaling B2B SaaS revenue from $10M to $50M+ ARR, with expertise in mid-market to enterprise sales motions ($20K-$100K+ ACV) and complex sales cycles (6-12 months)
• Revenue Growth Leadership: You've successfully driven revenue growth before by setting direction, adapting to the market, and getting your team aligned behind a clear plan
• Team Building Excellence: You've hired and grown sales teams through different stages of company growth. Coaching, development, and celebrating wins are second nature to you
• Cross-Functional Collaboration: Sales doesn't happen in a vacuum. You know how to collaborate closely with Marketing, Product, and Customer Success to deliver consistent, aligned go-to-market execution
• Sales Methodology Expertise: You bring a deep understanding of segmentation, lead generation, qualification frameworks, and how to build high-converting sales funnels
• New Market Development: You've taken new markets from zero to one. Whether it's launching into a new vertical, a different buyer persona, or a new region, you've developed go-to-market plans that get results
• Data-Driven Decision Making: CRMs, dashboards, forecasting, conversion rates, you know your way around the data and use it to guide smart decisions
• Complex B2B Sales: Experience with complex, multi-stakeholder B2B sales in regulated or safety-critical industries, with proven ability to navigate lengthy sales cycles and technical evaluations
• Consultative Selling: You believe in consultative selling, and you've succeeded in industries where trust and technical insight matter just as much as the product
• Executive Communication: Whether it's motivating your team, aligning with peers, or presenting to the CEO or board, you know how to tailor your message to the room

Desirable

• Our SaaS platform is redefining how aviation organisations manage safety, compliance and operations. We’re seeking a Sales Director who can consolidate and elevate our commercial function as we transition from mid-market strength to enterprise expansion
• This is a unique opportunity for a visionary yet hands-on leader to report directly to the CEO and shape the future of how we sell
• You'll unify sales efforts across teams and regions, work hand-in-hand with marketing and product to refine our go-to-market strategy, and build the infrastructure needed to scale
• You'll lead a team of 10+ sales professionals including Account Executives, SDRs, Account Managers, and Sales Operations, with plans for significant expansion
• We operate in a safety-critical industry where credibility and trust matter as much as product quality
• This role is not just about hitting numbers, it's about setting the tone for long-term relationships and market leadership. You'll drive our evolution from mid-market leader to enterprise player, scaling deal sizes from $40K to $100K+ ACV while maintaining velocity and win rates
• Sales Leadership & Strategy
• Develop and execute a unified sales strategy that supports company growth across segments and geographies
• Define segmentation, sales coverage, territory design, and team structure for maximum impact
• Build scalable sales processes for outbound, inbound, and channel motions with clear performance metrics
• Actively support strategic deals and executive-level relationships to accelerate pipeline conversion and drive market credibility
• Lead the evolution of our sales motion from mid-market to enterprise, managing complex 6-12 month sales cycles
• New Market Growth
• Identify and validate new market opportunities—industries, regions, and personas—with structured GTM approaches
• Lead the development of sales assets and messaging for emerging verticals
• Evolve pricing, packaging, and positioning to fit new use cases and larger deal sizes
• Drive expansion into enterprise accounts while maintaining mid-market momentum
• Cross-Functional Alignment
• Collaborate with Marketing team on ICP development, campaign strategy, and lead quality feedback
• Partner with Product team to deliver buyer feedback loops and shape go-to-market readiness for new features
• Work with Customer Success team to ensure a seamless transition from sale to onboarding and long-term expansion
• Team Building & Performance
• Hire, develop, and retain a high-performing sales team, including AEs and SDRs
• Foster a culture of continuous coaching, ownership, and customer-centricity
• Implement frameworks to support deal qualification and conversion in complex sales cycles
• Design and lead onboarding and ongoing sales training initiatives to ensure team readiness and consistency in messaging
• Revenue Operations & Insights
• Own forecasting, pipeline health, and conversion metrics using tools like Salesforce, Pipedrive or HubSpot
• Own annual sales planning including headcount forecasting, budget allocation, and quota assignment to support company-wide financial planning
• Collaborate with Revenue Operations to refine funnel analytics and identify performance levers
• Create dashboards and reporting to inform strategic decisions at the executive level