Keller Executive Search International

Transforming Organisations with Exceptional Leadership

VP of B2B Sales

SalesSalesFull TimeRemoteLeadTeam 11-50H1B No SponsorCompany Site LinkedIn

Location

United States

Posted

27 days ago

Salary

$180K - $230K / year

Seniority

Lead

Bachelor Degree7 yrs expEnglish

Job Description

• 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 • 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 • 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 • 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

Job Requirements

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

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