Location: Remote, USA
At Wealthbox, we serve thousands of financial advisors with our modern CRM software, which provides an easy way to manage client relationships, organize and execute workflow processes, and collaborate with a team in a powerful and beautiful software solution.
Wealthbox is seeking a Director, Sales (Mid Market) to join our rapidly growing organization. The Director, Sales (Mid Market) will lead a team of Account Executives focused on managing both inbound and outbound sales in a high-velocity sales environment. Our Account Executives have 2-5 years of closing experience, and you will play a critical role in training, coaching, and developing them into top performers.
As the bridge between the SVP, Sales and the Mid Market team, you’ll be responsible for translating strategy into actionable tactics, implementing scalable processes and fostering a winning sales culture. This is a rare opportunity to join Wealthbox at an inflection point—helping to refine our sales playbook to unlock accelerated growth, with clear pathways to advance your career.
Key Responsibilities:
Team Leadership & Development
- Lead, coach, and mentor a team of Account Executives to consistently achieve and exceed sales targets
- Conduct regular 1:1s, forecasting meetings, pipeline reviews, and performance evaluations to drive accountability and skill development
- Partner with Sales Enablement to create and deliver ongoing sales training tailored to AEs in a fast-paced, transactional selling environment
Sales Strategy & Execution
- Develop and refine high-velocity sales strategies for both inbound and outbound pipeline generation
- Implement processes, tools, and cadences that drive efficiency, speed-to-close, and win rates
- Partner with the Executive Team, Marketing and Sales Operations to optimize lead flow, territory design, and pipeline coverage
Operational Excellence
- Establish sales metrics, dashboards, and reporting to track team performance and identify improvement areas
- Experiment with and scale new sales tactics—creating a repeatable, measurable, and predictable revenue engine
- Act as the voice of the Mid Market sales team to Senior Leadership, ensuring alignment on goals and feedback loops
Culture & Growth
- Foster a culture of collaboration, learning, and healthy competition
- Identify and develop future leaders within the sales organization
Desired Skills & Experience:
- 3+ years of managing a high-velocity B2B SaaS sales team in a fast-paced, growing environment
- Proven track record of success as both a front-line leader and individual contributor
- Experience managing Account Executives with 2-5 years tenure and developing them into consistent quota achievers
- Exceptional communication skills & strategies designed for a remote environment
- Strong track record of building or scaling sales processes from scratch
- Data-driven decision-making with deep familiarity in pipeline management, forecasting, and KPI tracking
- Exceptional ability to design and deliver impactful sales training programs
- Skilled in diagnosing performance gaps and implementing targeted coaching plans
- Ability to thrive in an environment with minimal existing playbooks or processes
- Proficiency with Salesforce, Gong and a modern sales tech stack
Work schedule
- Full-time, weekdays during business hours (fully remote)
- Occasional travel for industry conferences, client meetings, and company offsite events
Benefits
- Competitive compensation (base + commission)
- Comprehensive health plan coverage
- 401k plan
- Paid time off
Interested? Email us a note at jobs@wealthbox.com with your resume and include a link to your LinkedIn profile.
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