Corporate Traveler - Director of Sales - Boston, MA

Flight Centre

1d•Onsite

About The Position

Corporate Traveler is seeking a strategic, hands-on Director of Sales to lead and scale our Business to Business (B2B) Small and Midsize Business (SMB) sales across the eastern United States, with New York representing a core growth market and a significant opportunity to expand our presence and market impact. This role is responsible for driving new customer acquisition, accelerating revenue growth, and building a high-performing sales culture grounded in accountability, coaching, and results. You will lead a team of Account Executives across multiple time zones, setting clear sales direction and providing hands-on coaching to support performance and development. Partnering closely with Product, Marketing, Enablement, Customer Success, and Engineering, you will help execute go-to-market strategies that drive growth in a fast-paced, evolving environment. This role requires flexibility to support business needs during peak sales periods and the ability to adapt quickly as priorities shift. This isn’t just a sales leadership role, it’s an opportunity to build and scale a critical growth market within the business. With strategic autonomy, strong organizational backing, and a rapidly evolving product, this role plays a pivotal part in establishing New York as a cornerstone of our growth story. Travel may be required for client meetings, team development, and leadership events as you build strong relationships and visibility across the organization. The right leader won’t simply deliver against targets; they will shape strategy, build scalable foundations, and help define the playbook for growth in one of the most competitive markets on the planet.

Requirements

Bachelor’s degree or equivalent experience
2+ years of experience building and leading front-line sales teams
4+ years of direct B2B sales experience selling to SMB or midmarket customers
Demonstrated success consistently achieving or exceeding sales targets
Strong leadership, coaching, and influencing skills
Excellent verbal, written, and presentation skills, including executive-level communication
Ability to analyze data and execute data-driven sales strategies
Deep understanding of the full B2B sales lifecycle and pipeline management
Strong change agility with the ability to lead and perform in fast paced, evolving environments
Experience using Salesforce and modern sales engagement tools

Nice To Haves

MBA or postgraduate qualification
Experience scaling sales teams in a high growth or evolving organization
Previous mid-level sales management experience
Experience within a Travel Management Company (TMC), particularly in B2B SMB or mid-market sales environments
Experience with sales enablement and performance frameworks
Experience with Outreach, Gong, or similar revenue intelligence platforms

Responsibilities

Establish sales objectives, forecasting, and quarterly/annual quotas aligned to company growth targets
Recruit, onboard, develop, and retain a high-performing team of Account Executives
Drive execution of go to market strategies, including new product introductions and market expansion
Maximize use of the sales tech stack to manage pipelines, improve productivity, increase lifetime contract value, and consistently exceed quota
Oversee the full sales lifecycle, ensuring pipeline health, forecast accuracy, and deal progression
Regularly engage in client and prospect meetings, supporting complex or strategic opportunities
Develop deep understanding of customer needs, market dynamics, and competitive positioning
Partner cross functionally with Product, Engineering, Customer Success, Enablement, and Marketing to align messaging and execution
Lead weekly sales meetings, providing clear expectations, performance insights, and transparent metrics
Deliver continuous coaching, feedback, and mentorship to elevate individual and team performance
Drive, refine, and evolve the sales strategy as the business scales
Contribute to a safe, inclusive, and accessible work environment where all Flighties feel welcomed, respected, and supported to thrive

Benefits

Paid Time Off: A comprehensive time off package, including up to 15 vacation days (prorated upon hire and increasing to 20 days after 2 years of employment), 5 sick days, 3 personal days, 1 Diversity Day, 1 Volunteer Day, and 8 recognized holidays annually.
Travel perks/discounts
Health & Wellness Programs and Employee Financial Wellness Services
National/International Award Nights and Conferences
Health benefits including, medical, dental, vision, gender affirming care, and fertility care
Insurance including hospital indemnity, AD&D, critical illness, long-term and short-term disability
Flexible Spending Accounts
Employee Assistance Program
401k program with partial match
Tuition Reimbursement Program
Employee Share Plan – Ability to purchase company stock on Australian Stock Exchange with partial company match, subject to terms and conditions
Global career opportunities in a network of brands and businesses