Enterprise Director of Sales
Location: Fully Remote (U.S.)
Travel: Approximately 10–15% for trade shows, client meetings, and partner events
Position Type: Full-Time
Compensation: Strong base salary + uncapped commissions
Reports To: Founder/CEO
Leadership: Member of the Destination Motivation Strategic Leadership Team (SLT)
About Destination Motivation
Destination Motivation helps companies dramatically increase their sales and close rates through our industry-leading vacation voucher programs and customer engagement strategies. We partner with leading home improvement and service companies across the country, helping them create stronger customer experiences while driving measurable revenue growth.
We have been recognized as the #1 Partner for Home Improvement Companies by Power100 and named one of the fastest-growing companies in the U.S. three years in a row on the Inc. 5000, with over 3,900 five-star reviews. As we expand into new industries and markets, we are building the senior team that will lead that growth.
About the Role
The Enterprise Director of Sales is a senior, executive-level role responsible for driving Destination Motivation’s growth into new clients, verticals, and strategic partnerships. This is an elevation of our traditional sales role for a proven leader who can close at the enterprise level while also shaping where and how the company grows.
As a member of the Strategic Leadership Team, you will work directly with company leadership to set business development priorities, refine go-to-market strategy, and help guide the continued evolution of the organization. The expectation is not only to generate new business, but to think strategically about where we can grow and how we build a stronger company for our clients, partners, and team.
This is a high-output, relationship-driven role for someone with a true builder mentality who wants major impact and significant earnings upside, and who wants to grow with Destination Motivation long term.
Key Responsibilities
New Business Development
Identify, pursue, and close new enterprise business across home improvement, services, and new target industries.
Build and manage a consistent, high-value pipeline of prospective clients.
Develop relationships with business owners, executives, sales leaders, and strategic partners.
Conduct discovery calls, product demonstrations, and strategy discussions with prospective clients.
Clearly communicate how the vacation voucher program increases close rates, reduces cancellations, and improves the customer experience.
Close new accounts and guide a smooth handoff into onboarding.
Sales Strategy & Market Growth
Help expand Destination Motivation into new verticals, industries, and strategic partnership channels.
Identify growth opportunities in the market and bring forward new ideas for revenue expansion.
Partner with leadership to refine sales messaging, positioning, and go-to-market strategy.
Share field feedback and insights to continuously improve the sales process and client experience.
Help shape long-term business development strategy as part of the Strategic Leadership Team.
Partnership Development
Identify, pursue, and leverage industry partnership opportunities to fill the pipeline and grow alongside partners.
Use existing partnership relationships to generate leads and build deep relationships within the partnership space.
Events & Relationship Building
Represent Destination Motivation at our 6–7 major industry trade shows each year, plus client and partner events.
Run the booth, host dinners and events, and put yourself in position to meet as many potential clients as possible.
Proactively engage prospects, partners, and industry leaders to create new opportunities, referrals, and long-term revenue.
Strategic Leadership Team
Contribute to high-level company strategy and identify new growth opportunities.
Help guide business development priorities and the continued evolution of the organization.
Bring forward ideas and insights that improve the company’s strategy, systems, and execution.
Internal Collaboration
Work closely with Sales, IT, Account Management, Client Success, Marketing, and Leadership to ensure smooth transitions from prospect to client.
Support and collaborate with the sales team on demos, company pipeline, and future opportunities.
Maintain accurate pipeline and activity records in the company CRM.
Participate in team meetings, strategy sessions, SLT discussions, and ongoing training.
What We’re Looking For
- Proven experience in enterprise sales, business development, partnerships, or revenue growth, ideally in home improvement, products, or service-based industries.
- Strong communication, presentation, and relationship-building skills, with the ability to build trust quickly with executives and owners.
- Comfortable presenting to and closing with business owners and leadership teams, including confidence in a one-call close.
- Strong CRM and pipeline discipline; organized and consistent in activity tracking (Hubspot experience a huge plus) but must have some CRM knowledge and be tech saavy.
- Self-starter who manages their own pipeline, priorities, and follow-up.
- Strategic thinker able to contribute at the leadership level.
- Willingness to travel as needed for trade shows, client meetings, and business development.
- Positive, high-energy approach and a strong work ethic, with a commitment to growing with the company long term.
- Utilizes AI to be proficient, and spend time on what matters most which is talking to and building relationships with potential clients and prospects.
Key Traits for Success
- Hustle mentality, relentless in pursuit of success.
- Entrepreneurial, competitive, and results-driven.
- Relationship-driven and strategic.
- Organized, accountable, and high-energy.
- Comfortable making new introductions and putting themselves out there.
- Motivated by both impact and earnings upside.
- Understands how to be engaging, fun and create dynamic calls.
- Great teammate!
Compensation & Earnings Upside
This role offers a strong base salary plus uncapped commission on collected sales revenue and performance incentives. Commission is earned on paid invoices following each closed deal, rewarding you directly for the revenue you create. (Specific base, commission rate, and any guaranteed ramp will be finalized in the formal offer.)
Competitive base salary.
Uncapped commission tied to collected revenue from accounts you close for a full year!
Performance incentives and significant total earnings upside as you build your book.
Work Environment & Benefits
Fully remote work environment with a flexible, entrepreneurial culture.
Approximately 10–15% travel for trade shows, client meetings, and partner events throughout the year.
Medical, dental, and vision plan options, with a strong portion covered by the employer.
Paid sick days, paid vacation, recognized national holidays, and a floating holiday.
Opportunity to grow within a rapidly expanding company and help build something meaningful.
Work Expectations
As a full-time employee, you are expected to work a minimum of 40 hours per week, generally Monday through Friday. Because our clients and prospects operate across all U.S. time zones, flexibility and availability outside standard hours may be required to deliver exceptional performance. Success in this role requires consistent outreach, strong follow-up, pipeline ownership, trade show participation, relationship building, and a relentless willingness to create opportunities rather than wait for them.
Equal Opportunity & At-Will Employment
Destination Motivation is an equal opportunity employer and values diversity in the workplace. We are committed to creating an inclusive environment for all employees and applicants.
Employment with Destination Motivation is at-will, which means that either the employee or the company may terminate the employment relationship at any time, with or without cause or advance notice, subject to applicable law. Nothing in this job description should be interpreted as creating a contract of employment, express or implied. Destination Motivation reserves the right to modify job duties, responsibilities, compensation, benefits, and employment policies at any time based on business needs.
Ready to Apply?
If you’re self-motivated, love building client relationships, and want to take full ownership of your success, we want to hear from you!
Email a cover letter and your resume with the subject line: “Enterprise Director of Sales Application – YOUR NAME” to Vida@IncreaseOurSales.com
Join Destination Motivation and help our clients achieve more—while sending their customers on the vacation of their dreams!
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GIVING BACK
Our culture here at Destination Motivation believes in giving back to those in need. Each quarter we choose a new project and dedicate time and resources into helping that cause. This year we are dedicating resources to an extremely worthy cause called The Ocean Cleanup. The Ocean Cleanup is a non-profit organization developing and scaling technologies to rid the oceans of plastic.
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