Head of Client Success

Location: Remote (U.S.)
Travel: ~10%
Compensation: $150,000 – $200,000+ (Base Salary + Commission + Performance Bonuses)
Reports To: President, Brett Thornton & Caleb Nelson, Founder/CEO

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. It's earned us recognition as both the #1 Partner for Home Improvement Companies by Power 100 and as one of the fastest-growing companies in the US three years in a row on the Inc. 5000.

As our company continues to scale, we are hiring a Head of Client Success to lead and develop our Account Management team while also managing several of our most strategic Tier 1 client relationships. This is a leadership role for someone who thrives in a fast-moving, entrepreneurial environment and wants to help build something special.

Position Overview

The Head of Client Success is responsible for leading and developing a team of Senior Account Managers and Junior Account Managers while also directly managing several key Tier 1 client relationships.

This role is both strategic and hands-on. The right leader will dive deeply into accounts, help the team identify growth opportunities, support high-stakes client meetings, and ensure every client is maximizing the value of the Destination Motivation program.

This leader will play a critical role in coaching performance, analyzing KPIs, strengthening culture, and helping our account teams operate at an elite level.

Key Responsibilities

Team Leadership & Coaching

• Lead and develop a team of Senior Account Managers and Junior Account Managers
• Hold regular daily and weekly meetings with Account Managers to review performance
• Coach team members on account strategy, growth opportunities, and client communication
• Provide real-time guidance on challenges, client escalations, and problem solving
• Build a culture of accountability, energy, and ownership across the team

Account Growth & Strategy

• Dive deeply into client accounts to identify opportunities for growth and expansion
• Partner with Account Managers to develop strategic account plans
• Identify wins, successes, and best practices that can be replicated across accounts
• Help the team drive increased voucher usage, engagement, and overall program success

Tier 1 Client Management

• Personally manage several high-value Tier 1 client relationships
• Conduct strategic client meetings, trainings, and business reviews
• Travel when needed to support major accounts or large client initiatives
• Participate in high-stakes client meetings alongside Account Managers

Account Division Performance Ownership

• Own overall account division performance, including voucher usage, client retention, expansion revenue, and client satisfaction
• Establish performance benchmarks and ensure the team consistently meets or exceeds them
• Hold team members accountable for results while providing the support and coaching needed to succeed

Performance & Data Leadership

• Track and analyze key account management KPIs
• Build and review reports that help drive performance improvements
• Use performance data to coach team members and improve results
• Identify trends across accounts and bring proactive solutions

Training & Client Success

• Conduct online meetings, trainings, and strategy sessions with clients
• Help Account Managers deliver high-impact client presentations
• Ensure every client fully understands and utilizes the Destination Motivation program

Culture & Leadership

• Lead by example with an entrepreneurial mindset and strong work ethic
• Build energy and motivation within the team
• Foster a culture of collaboration, growth, and accountability
• Run toward problems and solve them proactively rather than avoiding challenges

Operational Leadership

• Make decisive calls on client strategy, account prioritization, and internal resource allocation
• Resolve complex client issues quickly and confidently without unnecessary escalation
• Continuously improve internal account management processes and playbooks
• Recruit, hire, and train future Account Managers as the business grows

What We’re Looking For

• Proven leadership experience managing Account Managers, sales teams, or client success teams
• Strong experience managing large client relationships
• Ability to analyze KPIs, performance metrics, and account data
• Exceptional communication and presentation skills
• High emotional intelligence and strong people leadership abilities
• Entrepreneurial mindset with a builder mentality
• A problem solver who thrives in fast-paced environments
• Comfortable working remotely while leading a distributed team

Key Traits for Success

• High energy and motivating leadership style
• Hustler mentality with strong ownership mindset
• Strategic thinker who also enjoys being hands-on
• Ability to quickly spot opportunities and solve problems
• Passion for helping teams win and grow

Success Metrics

• Increased voucher usage across the client base
• High client retention and strong expansion revenue
• Account Managers consistently hitting performance targets
• Strong relationships with Tier 1 clients
• A high-energy, accountable account management culture

Work Environment & Benefits

• Remote work environment
• Approximately 10% travel for client meetings and trainings
• Competitive compensation package including salary, commission, and performance bonuses
• Health benefits
• Vacation and PTO package
• Opportunity to grow with a rapidly expanding company

Ready to Apply?

Email your resume and a brief introduction with the subject line:
“Head of Client Success Application – YOUR NAME” to Vida@IncreaseOurSales.com

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.