Overview
We are seeking a hands-on Director, Sales Development to lead a lean, early-stage sales team (BDRs and Associate Account Executives), establish operating discipline and define performance standards in a fast-moving scale-up environment. This is a true player-coach role for a sales leader who thrives in ambiguity, operates comfortably in the weeds, and brings discipline, clarity, and momentum to high-velocity sales.
Own end-to-end execution under the strategic leadership and direction of the P/COO while developing a high-performing sales team. This role is fully remote and reports to the President & COO.
Key Responsibilities
1. Lead, Coach, and Invest in a Growing Sales Team
- Coach Account Executives through live calls, deal reviews, and daily execution. Model best practices and grow the team’s experience in core sales skills like discovery, demos, and follow-up.
- Provide clear, actionable feedback and hands-on enablement to accelerate team development and performance motivating them to succeed and achieve targets.
- Intentionally build team cohesion, trust, and shared accountability by establishing clear operating norms, regular team rhythms, and meaningful connection points that foster belonging, momentum, and ownership across a fully remote, distributed team.
2. Drive High-Velocity Sales Execution
- Build and execute outbound motions across defined ICPs, including list building, sequencing, and messaging. Lean on existing playbooks, iterating and refining with new insights.
- Establish consistent activity expectations and funnel discipline that steadily grows qualified pipeline creating predictability and foresight into team performance and revenue drivers by segment.
- Partner closely with the CEO and COO on enterprise opportunities by supporting prospecting, discovery, and demos; build the team’s capability to meaningfully contribute to complex enterprise sales motions while also driving effective execution across SMB and early-stage customer segments.
3. Own Sales Operations & HubSpot Excellence
- Run daily, weekly, and monthly sales operations cadence, including pipeline management, activity tracking, and conversion analysis to monitor progress, establish milestones, and improve visibility.
- Ensure pristine HubSpot reporting and data hygiene, partnering with the HubSpot Admin to deliver daily exception reports, weekly performance views, and monthly executive metrics.
4. Deliver Executive-Ready Insights
- Translate sales data into clear insights for the executive team, highlighting trends, risks, and opportunities.
- Ensure leadership has consistent visibility into funnel health, rep performance, and execution quality.
- Partner closely with Finance to support revenue predictability through accurate pipeline reporting, forecasting inputs, and clear articulation of leading indicators and risks.
5. Build Product Mastery & Sales Enablement
- Develop expertise in the digital health and wellness industry, competitive products and service offerings, and varied customer use cases, and how our solutions solve customer pain points.
- Capture unanswered prospect questions and objections to build and maintain a living Sales knowledge base for ongoing training and enablement.
- Collaborate closely with Solutions Engineering, Customer Success, and Engineering to stay aligned as the product and business evolve.
What Success Looks Like
- Sales team executes confidently, consistently, and with increasing independence.
- HubSpot data and reporting are clean, reliable, and trusted by leadership.
- Repeatable outbound motions produce steady, predictable pipeline growth.
- Sales processes flex and improve as the business scales.
Qualifications
- 5+ years’ experience leading or coaching BDRs and/or junior Account Executives in a high-growth or scale-up environment. Deep understanding of the full sales cycle and ability to coach and motivate teams of mixed experience.
- Strong hands-on sales operations background with deep HubSpot administration and reporting expertise. Experience balancing progress and perfection in an evolving, fast-moving environment.
- Ability to quickly ramp into complex, regulated industries such as telehealth. Committed and curious to understand the industry, competitors, and value proposition.
- Proven ability to operate in ambiguity, flex priorities, and lead teams through change taking strategic direction and brining execution excellence.
- Clear communicator with a bias toward action, accountability, and continuous improvement.
Compensation & Leveling
- This role is scoped for a hands-on sales leader in a scale-up environment. Title and compensation will be calibrated based on experience and demonstrated ability to build, coach, and operate a high-velocity sales function.
- Target compensation is in the range of $140,000 - $170,000 OTE (80/20 mix).
- Variable compensation is aligned to pipeline creation, execution excellence, and team development outcomes.