Keller Executive Search · 12 hours ago
Director of B2B Sales #0209
United States
Full-time
Remote
Director/Executive
$180K/yr - $230K/yr
7+ years expKeller Executive Search is representing one of the nation’s largest telemedicine providers, which is seeking a VP of B2B Sales to build and scale their enterprise revenue engine. This role involves direct ownership of enterprise sales, go-to-market execution, and early-stage partner development, focusing on creating repeatable sales motions and leading a high-performing team.
Staffing & Recruiting
Responsibilities
Build, scale, and lead the B2B sales organization (AEs, SDRs, CSMs, Partner Success, Sales Engineering)
Establish a culture of execution excellence, accountability, and data-driven decision-making
Design compensation plans, quota structures, onboarding programs, and career ladders
Train teams on healthcare sales methodology, PMPM pricing models, and ROI-led enterprise selling
Personally drive early enterprise and partner-led selling motions
Collaborate with marketing on PPC, content, events, and ABM initiatives
Build repeatable outbound → discovery → demo → proposal → close motions
Define ICP prioritization, segmentation, buyer personas, and channel-by-channel messaging
Develop sales playbooks, value propositions, and presentations tailored to employers and brokers
Establish enablement strategies for brokers and consultants
Work cross-functionally with Clinical Operations, Compliance, Product, and Legal
Lead high-value sales conversations with HR leaders, founders, COOs, and benefits decision-makers
Manage complex PMPM pricing structures, multi-state deployments, and enterprise SLAs
Own end-to-end enterprise deal execution including discovery, proposals, negotiation, and contracting
Report monthly and quarterly revenue performance to the CEO and executive leadership
Implement sales dashboards, KPIs, and performance tracking
Own pipeline operations, forecast accuracy, and revenue pacing
Qualification
Required
Demonstrated success closing mid-market and enterprise employer or benefits deals
Experience building and managing multi-channel sales teams (AEs, SDRs, CSMs)
Bachelor's degree required (Business, Healthcare Administration, Finance, or related preferred)
Direct experience selling PMPM, PEPM, per-visit, or membership-based healthcare offerings
Strong analytical and forecasting capabilities
Strong understanding of healthcare compliance, clinical operations, and virtual care delivery
Ability to build systems, teams, and processes from scratch
Exceptional enterprise sales leadership and negotiation skills
Thrives in fast-moving, founder-led environments
Proven track record scaling B2B revenue from early traction to meaningful ARR growth (e.g., $0–$10M, $5M–$30M+)
Deep familiarity with the employer benefits ecosystem
7–12+ years of B2B sales leadership experience in telehealth, healthtech, employer benefits, digital health, or adjacent healthcare sectors
Excellent cross-functional collaboration and communication
Experience building out a sales department/team from scratch
Experience building out and enforcing KPIs
Able to take full ownership from day 1
Preferred
Established relationships with benefits brokers, consultants, TPAs, or employer networks
Background negotiating enterprise SaaS or hybrid healthcare contracts
Experience at digital health or consumer health companies (Teladoc, One Medical, Amwell, Included Health, Carbon Health, Thirty Madison, Hims, Hers, Ro, Nurx, or similar)
MBA or advanced degree
Experience selling into staffing, gig economy, or distributed workforce populations
Benefits
Performance-based incentive structure (to be developed with successful candidate)
Meaningful equity stake
Fully remote position – work from anywhere
Growth opportunity: Full ownership of the sales side of the business with ability to shape team structure, processes, and strategy
Career path: Small organization with ability to make a significant impact and carve out the team to match your vision
Aggressive expansion phase: Join at a pivotal moment as the company shifts from organic marketing growth to enterprise sales-driven growth
Company
Keller Executive Search
Keller Executive Search is a boutique executive recruitment and advisory firm dedicated to connecting top-tier talent with leading organizations worldwide.
11-50 employees
Funding
Current Stage
Early StageCompany data provided by crunchbase