[All remote jobs](https://jobicy.com/jobs.md)Open role[![Garner Health logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/08/5ba0f621-221.png)](https://jobicy.com/company/garner-health.md)Remote opportunity at[Garner Health](https://jobicy.com/company/garner-health.md) # Enterprise Sales VP, Labor and Trust Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/garner-health.md)Share9 Aug 2026Published34Listing views0Application actions9 Sep 2026Apply before Opportunity details ## About this role. AI SummaryGarner is a healthcare technology company transforming the U.S. healthcare system by using proprietary clinical metrics and data to guide members to high-quality doctors, reducing costs and improving care. As Enterprise Sales VP for Labor and Trust, you will lead direct sales to large Taft-Hartley and public-sector union funds, owning the full sales cycle. This individual contributor role requires deep expertise in labor health & welfare funds, the ability to navigate joint labor-management boards, and a track record of building high-level relationships. You will be part of a fast-growing company that has saved $1B in healthcare costs and doubled five years running, with a mission-driven culture focused on impactful outcomes. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis role is extremely challenging due to the complex, multi-stakeholder sales cycles involving labor and management boards, requiring deep domain expertise in Taft-Hartley funds and the ability to influence diverse parties. The niche market and high expectations from a scaling startup further elevate the difficulty. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job medianHighly competitive$450,000US market range$300k–$600k0$660k AI insightThe offered salary range of $425,000-$475,000 is highly competitive, placing it well above the median for similar enterprise sales VP roles in the healthcare technology sector. This reflects the seniority and niche expertise required for Taft-Hartley fund sales. The market range for such positions typically spans from $300K to $600K depending on company stage, quota, and commission structure, and this offer sits at the upper end, indicating a strong total compensation package. ## Core skills Skills and capabilities most closely associated with this opportunity. [Enterprise Sales](https://jobicy.com/jobs?search_keywords=Enterprise%20Sales.md)[Healthcare Benefits](https://jobicy.com/jobs?search_keywords=Healthcare%20Benefits.md)[Taft-Hartley](https://jobicy.com/jobs?search_keywords=Taft-Hartley.md)[Labor Unions](https://jobicy.com/jobs?search_keywords=Labor%20Unions.md)[Sales Strategy](https://jobicy.com/jobs?search_keywords=Sales%20Strategy.md)[Pipeline Management](https://jobicy.com/jobs?search_keywords=Pipeline%20Management.md)[Stakeholder Engagement](https://jobicy.com/jobs?search_keywords=Stakeholder%20Engagement.md)[Data Analysis](https://jobicy.com/jobs?search_keywords=Data%20Analysis.md)[AI Tools](https://jobicy.com/jobs?search_keywords=AI%20Tools.md)[Public Sector Funds](https://jobicy.com/jobs?search_keywords=Public%20Sector%20Funds.md) Cover letter sampleDear Hiring Team, I am excited to apply for the Enterprise Sales VP, Labor and Trust position at Garner. With over a decade of enterprise sales experience in healthcare benefits and a specialized focus on Taft-Hartley funds, I have consistently exceeded sales quotas by building trusted relationships with trustees, fund administrators, and labor consultants. I understand the unique dynamics of joint labor-management boards and can effectively present value propositions that resonate with both sides. Garner's mission to transform healthcare through data-driven insights aligns perfectly with my passion for creating measurable impact. I look forward to bringing my expertise to your ambitious team and contributing to your continued growth. Copy Sample interview questionsDescribe your experience selling to Taft-Hartley funds. How do you navigate the joint labor-management board dynamics?I have spent the last five years selling to multiemployer funds. I typically begin by building credibility with the fund administrator and actuary, then secure a presentation to the full board. During these presentations, I address the priorities of both sides: for labor, quality of care and member satisfaction; for management, cost savings and risk reduction. By using data to demonstrate outcomes that matter to both groups, I can align the labor and management trustees around a shared decision. How do you manage a complex, long sales cycle with multiple stakeholders? I use a disciplined CRM approach to map all stakeholders, track their engagement levels, and identify potential champions. I segment decision-makers by their influence and tailor my messaging to each one's specific concerns. I maintain momentum through regular check-ins, providing educational material, and bringing in internal subject matter experts when needed. This ensures that no stakeholder is left behind and the deal progresses toward closure. How would you use data literacy to sell Garner's solution to labor funds? I would leverage Garner's proprietary clinical metrics to create customized presentations that show a fund's specific participant population and potential savings. By analyzing market trends and competitor offerings, I can position Garner's unique value proposition. I would also track outcome data from similar funds to build a compelling case study for each prospect. Why do you want to work at Garner, and how does our mission resonate with you? The opportunity to transform the U.S. healthcare system is deeply motivating. I have worked with union families and seen the challenges of rising healthcare costs and inconsistent quality. Garner's proven model, which has saved $1B and helped millions of people, demonstrates that change is possible. I want to be part of a company that delivers measurable outcomes, and my sales expertise can help expand this impact to more labor funds. What strategies would you use to build a pipeline in a new national territory? I would start by leveraging my existing relationships within the labor consultant ecosystem, such as Segal and other actuarial firms, to gain introductions to fund administrators. I would also attend industry conferences like IFEBP to network directly with trustees and administrators. Additionally, I would combine targeted outreach with a referral incentive program and use data analytics to prioritize funds based on size, participant count, and potential value. ## What you’ll be part of Garner is on a mission to transform the U.S. healthcare system — and we’re the only proven player doing exactly that. We partner with employers to redesign how healthcare works: applying 550+ proprietary clinical metrics across 80+ specialties to a dataset of 320M+ patients to identify the best-performing doctors, then using compelling incentives to steer members to the care that helps them get healthier, faster. The result is a rare “win win” — better care and lower costs for both members and employers. In just five years, our work has helped over 2.5 million people access higher-quality care and saved $1B in healthcare costs. We recently raised our Series E and have doubled five years running. If you’ve ever wanted your work to solve a problem that touches every person in this country, this is the opportunity to do exactly that. You’d be joining a team fundamentally reimagining healthcare in the U.S. — and using AI to scale that impact further and faster than anyone else can. ## Who we want This is a role for someone who wants to work on a hard problem, deliver real impact and be pushed to be the best version of themselves. As an Enterprise Sales VP, you’ll be embedded in the Enterprise Sales team and report directly to the VP, Public and Labor. The Enterprise Sales VP, Labor and Trust will expand our footprint with large labor health & welfare funds through direct sales. This is an individual contributor seat with a defined national territory: a named book of private multiemployer Taft-Hartley funds and public-sector union funds at 10,000 to 100,000 participants. We are expanding our team in order to continue to hit our ambitious Enterprise Sales goals. We are searching for a candidate who possesses the exceptional ability to establish and cultivate high-level relationships, as this will be instrumental in our pursuit of growth and innovation. ## What you will do * Own the direct sales cycles and deploy sales objectives through the preparation and measuring of sales quotas, prospecting and pipeline management across a named national book of labor health & welfare funds * Sell to boards of trustees: build fund office relationships, navigate joint labor-management board dynamics, and win both the labor and management sides of the room * Keep current with market knowledge and competitor products to effectively communicate the value proposition of a relationship with Garner * Support the development of new, strategic relationships with fund professionals (administrators, actuaries, counsel, and consultants) and carrier labor channels, including working the conference circuit (IFEBP), and influence the buying decision ## What we’re looking for * Bachelor’s degree and 7+ years of deep sales experience with a focus on health benefits (medical, ancillary, vendor) via brokers, consultants, and insurers * 5+ years selling into labor / Taft-Hartley funds strongly preferred, with fluency in how these funds actually work: joint boards, collective bargaining linkage, and fund professionals (administrator, actuary, counsel, investment consultant) * Existing, reference-checkable relationships with trustees, fund administrators, and the labor consultant ecosystem (Segal above all), plus credibility in the room with union leadership * A data literacy with the ability to turn complex, disparate datasets into insights that drive actions * Proven experience with developing processes (sales playbooks, KPIs, collateral creation, etc), and executing on sales strategies to promote long term success * A desire to do work that matters: and to be held to a high standard while doing it. You’re energized by a mission with measurable outcomes, not just good intentions. You engage with AI tools as part of how you do your best work, and hold yourself accountable to outcomes that matter beyond your team’s metrics. ## What you’ll get here You’ll work on problems that matter, at a company working to change healthcare at scale. You’ll work at the intersection of AI and systemic healthcare reform, where the problems we solve are as interesting and compelling as the mission. At Garner, you’ll take on real, ambitious problems with real ownership and autonomy, alongside exceptional, principles-based people who genuinely want you to win. It’s demanding by design. You’ll be challenged to stretch beyond what you thought possible and receive consistent coaching to help you grow and do the best work of your career. This isn’t the right fit for everyone, and that’s intentional. The people here are driven by what’s at stake for real people, and that’s what gives our intensity its purpose. ## Where you will work: Garner is headquartered in NYC, but this position is available for individuals who are comfortable with remote work and occasional travel to HQ. Visa sponsorship: Please note: we are unable to sponsor or take over sponsorship of an employment visa at this time. ## Compensation The target total comp (inclusive of base + bonus) range for this role is $425,000 – $475,000. Individual compensation will depend on qualifications, skills, and applicable laws. In addition to base compensation, this role is eligible to participate in our equity incentive plan and benefits package, including: flexible PTO, Medical/Dental/Vision plan options, 401(k) with company match, flexible spending accounts, Teladoc Health, and more. Few roles offer this combination: work that is genuinely hard, a mission that is genuinely important, and a team that is genuinely invested in your success. If that’s what you’re looking for, we’d love to meet you. ## Fraud and Security Notice: Please be aware of recent job scam attempts. Our recruiters use [getgarner.com](http://getgarner.com/) and [garnerhealth.com](garnerhealth.com) email domains exclusively. If you have been contacted by someone claiming to be a Garner recruiter or a hiring manager from a different domain about a potential job, please report it to law enforcement [here](https://www.ic3.gov/Home/ComplaintChoice) and to [candidateprotection@garnerhealth.com](mailto:candidateprotection@getgarner.com). ## Equal Employment Opportunity: Garner Health is proud to be an Equal Employment Opportunity employer and values diversity in the workplace. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. Garner Health is committed to providing accommodations for qualified individuals with disabilities in our recruiting process. If you need assistance or an accommodation due to a disability, you may contact us at [talent@garnerhealth.com](mailto:talent@getgarner.com). 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