Transforming Organisations with Exceptional Leadership

Director of B2B Sales

SalesSalesFull TimeRemoteTeam 11-50H1B No SponsorCompany Site LinkedIn

Location

United States

Posted

24 days ago

Salary

$180K - $230K / year

Bachelor Degree7 yrs expEnglish

Job Description

• 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

Job Requirements

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