VP of B2B Sales

Our client is one of the nation's largest telemedicine companies, delivering fast, affordable virtual care to millions of patients nationwide. Their platform supports acute, chronic, and lifestyle conditions through virtual medical services, medication delivery, AI-powered workflows, and proprietary care technology.

As they expand aggressively into B2B markets including employers, staffing organizations, benefits networks, and telehealth platform partnerships, they're seeking a VP of B2B Sales to build and scale their enterprise revenue engine from the ground up.

This is a hands-on builder role requiring direct ownership of enterprise sales, go-to-market execution, and partner development in the early phase. You'll validate ICPs, close early enterprise and broker-led deals, and establish repeatable sales motions. As traction is proven, you'll scale a high-performance organization across multiple channels.

Core Responsibilities:

Leadership & Organizational Development

• Personally lead early enterprise and partner-driven sales efforts
• Build, scale, and manage the B2B sales organization (AEs, SDRs, CSMs, Partner Success, Sales Engineering)
• Design compensation plans, quota structures, onboarding programs, and career ladders
• Establish a culture of execution excellence, accountability, and data-driven decision-making
• Train teams on healthcare sales methodology, PMPM pricing models, and ROI-driven enterprise selling

GTM Strategy & Execution

• Define ICP prioritization, segmentation, buyer personas, and messaging by channel
• Build repeatable outbound → discovery → demo → proposal → close motions
• Develop sales playbooks, value propositions, and presentations tailored to employers and brokers
• Collaborate with marketing on PPC, content, events, and ABM programs
• Establish broker and consultant enablement strategies

Enterprise Sales Leadership

• Lead high-value sales conversations with HR leaders, founders, COOs, and benefits decision-makers
• Own end-to-end enterprise deal execution including discovery, proposals, negotiation, and contracting
• Manage complex PMPM pricing structures, multi-state deployments, and enterprise SLAs
• Work cross-functionally with Clinical Operations, Compliance, Product, and Legal

Pipeline & Revenue Management

• Own pipeline management, forecasting accuracy, and revenue pacing
• Implement sales dashboards, KPIs, and performance tracking
• Report monthly and quarterly revenue performance to CEO and executive leadership

Requirements

Essential:

• Bachelor's degree required (Business, Healthcare Administration, Finance, or related field preferred)
• 7–12+ years of B2B sales leadership experience in telehealth, healthtech, employer benefits, digital health, or adjacent healthcare sectors
• Proven track record building and scaling B2B revenue from early traction through meaningful ARR growth (e.g., $0–$10M, $5M–$30M+)
• Direct experience selling PMPM, PEPM, per-visit, or membership-based healthcare offerings
• Experience building and managing multi-channel sales teams (AEs, SDRs, CSMs)
• Demonstrated success closing mid-market and enterprise employer or benefits deals
• Strong understanding of healthcare compliance, clinical operations, and virtual care delivery
• Exceptional enterprise sales leadership and negotiation skills
• Deep familiarity with the employer benefits ecosystem
• Strong analytical and forecasting capabilities
• Ability to build systems, teams, and processes from scratch
• Excellent cross-functional collaboration and communication
• Thrives in fast-moving, founder-led environments
• Experience building out a sales department/team from scratch
• Experience building out and enforcing KPIs
• Able to take full ownership from day 1

Preferred:

• MBA or advanced degree
• Experience at digital health or consumer health companies
• Established relationships with benefits brokers, consultants, TPAs, or employer networks
• Experience selling into staffing, gig economy, or distributed workforce populations
• Background negotiating enterprise SaaS or hybrid healthcare contracts

Benefits

• Competitive base salary: $180,000 - $230,000 (depending on experience)
• 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

Equal Employment Opportunity and Non-Discrimination Policy 

Equal Employment Opportunity Statement: Both Keller Executive Search and our clients are Equal Opportunity Employers. For all positions, whether with Keller Executive Search or our clients, qualified applicants will receive consideration for employment without regard to race, skin color, religion, sex, sexual orientation, gender identity, gender expression, national origin, age, protected veteran status, disability, genetic information, or any other legally protected status. 

Commitment to Diversity: Keller Executive Search and its clients are committed to fostering a diverse and inclusive work environment where all individuals are valued and respected. 

Reasonable Accommodations: Both Keller Executive Search and our clients are committed to providing reasonable accommodations to individuals with disabilities and pregnant individuals. We engage in an interactive process to determine effective, reasonable accommodations.  

Compensation Information: For client positions, compensation information is available in the job post. If not provided, it will be shared during the interview process in accordance with applicable laws. When required by law, salary ranges will be included in job postings. Actual salary may depend on skills, experience, and comparison to current employees in similar roles. Salary ranges may vary based on role and location. 

Compliance with Laws: Both Keller Executive Search and our clients comply with federal, state, and local laws governing nondiscrimination in employment. This policy applies to all employment terms and conditions, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training. 

Workplace Harassment: Both Keller Executive Search and our clients expressly prohibit any form of workplace harassment based on race, skin color, religion, gender, sexual orientation, gender identity or expression, national origin, age, genetic information, disability, or veteran status. 

E-Verify Participation: Keller Executive Search and/or our clients may participate in E-Verify. Information about E-Verify participation will be provided during the application process where applicable. 

Privacy and Pay Equity: 

• California Residents: For more information about the categories of personal information we collect for recruiting and employment purposes, please review our Privacy Policy at www.kellerexecutivesearch.com. 

• Colorado, Nevada, New York City, California, and Washington Residents: Compensation information is available in the job post or will be provided during the interview process if not initially available. 

• Both Keller Executive Search and our clients are committed to pay equity and conduct periodic pay equity analyses in accordance with applicable laws. 

State-Specific Information: 

• Rhode Island: We do not request or require salary history from applicants. 

• Connecticut: We provide wage range information upon request or before discussing compensation. 

• New Jersey: We do not inquire about salary history unless voluntarily disclosed. 

Veteran Status: Both Keller Executive Search and our clients provide equal employment opportunities to veterans and comply with applicable state laws regarding veteran preference in employment. If you are a veteran, please inform us during the application process. 

Use of Artificial Intelligence in Recruitment 

Keller Executive Search and our clients may use artificial intelligence (AI) tools to assist in the recruitment and candidate evaluation process. These tools are used exclusively to support human decision-making by helping to review and assess candidate qualifications and materials. AI is never used to automatically reject, disqualify, or make final hiring decisions about candidates. All AI-assisted evaluations are reviewed by experienced recruitment professionals, and all hiring decisions are made by qualified human recruiters. Our use of AI is designed to enhance fairness, consistency, and efficiency while maintaining our commitment to equal employment opportunity and non-discrimination principles. 

Genetic Information: In accordance with federal and state laws, both Keller Executive Search and our clients do not discriminate based on genetic information. We do not request or require genetic information from applicants or employees, except as permitted by law. 

Local Laws: Both Keller Executive Search and our clients comply with all applicable local laws and ordinances regarding employment practices in the areas where we operate. 

Note: This job posting may be for a position with Keller Executive Search or one of our clients. The specific employer will be identified during the application and interview process. Employment laws and requirements may vary depending on the employer and location.