Keller Executive Search International

Director of B2B Sales

Keller Executive Search International

full-time

Posted on:

Location Type: Remote

Location: United States

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Salary

💰 $180,000 - $230,000 per year

Job Level

Lead

About the role

  • 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

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
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
B2B salesPMPM pricing modelsenterprise sellingsales forecastingsales leadershipnegotiationKPI enforcementsales playbookspipeline operationsrevenue performance tracking
Soft Skills
analytical capabilitiescross-functional collaborationcommunicationexecution excellenceaccountabilitydata-driven decision-makingteam buildingprocess developmentadaptabilityleadership
Certifications
Bachelor’s degreeMBA or advanced degree