Company Overview

For over 21 years, Track has provided integrated software and marketing solutions for the hospitality industry, anchored by our flagship Track Property Management System and other products under the Track banner.

Our single-vendor ecosystem equips growing vacation rental companies with all the enterprise-class tools they need to scale. With ongoing investments in platform development, 70+ integration partners, and a growing suite of native features, Track, built on a customer-obsessed mindset, empowers hospitality professionals to achieve digital transformation and operational excellence. Our development includes a focus on leveraging AI-driven tools to enhance pricing, distribution, and guest communication 

Our Core Values reflect the behaviors that shape the tone of how we work with each other, our partners, and our customers:

• Serve Others: Nurturing growth to help others succeed

• Grit: Taking ownership and never giving up on what matters most

• Create the Future: Innovating to disrupt the status quo 

Why Join Us?

• Be part of a fast-moving, dynamic team focused on growth and success.

• Work alongside a talented, collaborative, and supportive team.

• Work for a portfolio company offering a one-vendor solution for SaaS technology, marketing, and distribution.

• Help reshape the hospitality industry through technology and service innovation.

Are you ready to Level Up! Join our growing team as a Director of Sales!

At Track, we combine deep hospitality expertise with forward-thinking technology and a customer-obsessed mindset to help property managers win.

Track is proud to be named an Inc. 5000 Fastest Growing Company in America and a People’s Choice Award winner, reflecting our commitment to innovation, service, and customer success. Track is an end-to-end SaaS and Service Operating Platform for Short Term Rental, proudly named an Inc. 5000 Fastest Growing Company in America. For over 21 years, we have helped hospitality professionals achieve digital transformation and operational excellence. Our single-vendor ecosystem includes 70+ integration partners and a growing list of native features.

This is a true sales leadership role for a proven leader ready to drive results through a team. Reporting to the VP of Sales, you’ll lead a small team of Mid-Market Account Executives and Customer Account Executives (CAEs), carrying the team quota and driving daily, weekly, and monthly ownership and execution across new business, renewals, and expansion. You’ll own forecasting, sales process rigor, and team performance, partnering cross-functionally to grow Track’s footprint in the vacation rental industry.

What You'll Do

Team Leadership & Execution

• Lead, coach, and develop a team of Mid-Market Account Executives and Customer Account Executives to achieve team quota.

• Drive daily, weekly, and monthly ownership and execution through structured 1:1s, pipeline reviews, and team meetings.

• Deliver performance reviews, build development plans, and manage performance improvement plans when needed.

• Develop and implement sales training programs so the team is equipped with the skills and knowledge to succeed.

• Serve as the escalation point for complex customer situations and sales cycles, supporting the team in closing deals and resolving issues.

• Share best practices and drive consistency in new business, renewals, and expansion efforts across the team.

• Hire, train, and onboard new team members; build and maintain enablement materials, playbooks, and ramp plans.

• Partner with the VP of Sales on headcount planning, team structure, and ramp capacity to support segment growth.

Sales Strategy & Execution

• Develop and implement sales strategies to increase bookings and expand the customer base.

• Develop and execute comprehensive sales plans and programs, both short and long-range, to support the sales, bookings, and branding objectives of the organization.

• Develop and manage the team's sales pipeline to ensure a steady flow of opportunities.

• Analyze sales data and market trends to identify opportunities for growth.

• Provide analytical expertise and market insights that drive strategic decision-making and maximize the market potential of the Track portfolio.

• Discover, develop, and maintain an in-depth understanding of the industry, market trends, and customer insights.

• Contribute to territory design, account segmentation, and playbook development.

Forecasting & Operational Rigor

• Own team pipeline accuracy and deliver bookings, renewal, and expansion forecasts to the VP of Sales on a regular cadence.

• Monitor team progress toward goals daily, weekly, and monthly; identify performance gaps and take action to close them.

• Ensure CRM hygiene and reporting standards are met consistently across the team.

• Accountable to the team's monthly, quarterly, and annual quota attainment.

Cross-Functional & Industry Leadership

• Collaborate with Marketing, Product, and Customer Success to ensure alignment and support for sales initiatives.

• Act as the voice of the customer internally by providing feedback to Product, Support, and leadership teams.

• Participate in or lead user conferences, trade shows, demos, customer and partner meetings, press tours, and other industry events.

• Ensure compliance with company policies, procedures, and ethical standards.

Required Qualifications

• Bachelor's degree or equivalent experience.

• 4+ years of experience in account management, customer success, or sales, preferably in SaaS or a similar industry.

• 3+ years of direct people management experience leading a sales team to quota (required).

• Proven track record of leading a team to consistently meet or exceed revenue targets through new business, renewals, and expansion.

• Demonstrated experience building, scaling, or restructuring a sales team, including hiring, onboarding, and ramping reps.

• Experience owning a forecast and presenting bookings, pipeline, and risk to senior leadership.

• Excellent communication, negotiation, and problem-solving skills.

• Strong organizational skills with the ability to manage multiple priorities in a fast-paced environment.

• Experience managing team pipeline and reporting in a CRM (Salesforce, HubSpot, or similar).

This role is perfect for someone who is

• A proven sales leader who drives results through a team and holds people accountable to outcomes.

• A coach at heart, energized by helping others succeed and develop in their careers.

• Disciplined about forecasting, pipeline accuracy, and sales process rigor.

• A strategic and critical thinker who can solve problems creatively and efficiently.

• A relationship builder with a customer-first mindset and a passion for customer advocacy.

• Adaptable, quick to learn, and comfortable navigating change in a fast-paced SaaS environment.

• Enthusiastic about technology, innovation, and improving the customer experience.

Compensation & Benefits

Annual Salary
An expected base salary of $120,000, with an OTE of $$172,000 made up of base plus variable incentive tied to team and company performance. Final compensation will be determined based on factors such as relevant skills, experience, education, and geographic location. 

Benefits

• Full medical, dental, and vision coverage

• Flexible Paid Time Off

• Unlimited access to professional training and development

• Health Savings Account with up to a $2,000 annual match

• Up to $900 in annual Wellness Rewards

• Flexible work environment

• Free life insurance and long-term disability coverage

• Flexible Spending Accounts

• Retirement plan with employer match

• $150 quarterly gift for personal use

• Competitive wages

• Work with an amazing team!

Diversity and Inclusion

We celebrate diversity of thought, culture, and background and are committed to creating an inclusive environment. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, disability, or veteran status or any other protected status under applicable federal, state, or local law. We comply with all applicable laws governing nondiscrimination in every location where we operate and encourage individuals from all backgrounds to apply.