Island Health

Founding Sales Executive - JobTwine

Island Health$110K — $125K *
US-AnywhereRemote in United States
Enterprise Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5-10 years of B2B SaaS sales experience, ideally in AI, HRTech, or recruiting automation.
  • Successful track record selling to Director+ or VP of TA, HR, or Business Unit Heads in mid-market companies.
  • Experience with complex, multi-stakeholder deals ranging from $50K to $500K ARR.
  • Proven ability to thrive in early-stage environments and build processes independently.
  • Exceptional written, verbal, and presentation skills, capable of compelling storytelling.

Responsibilities

  • Hunt and secure new clients in target verticals including Tech, IT Services, SaaS, and Healthcare Staffing.
  • Develop and execute robust outbound and account-based marketing (ABM) strategies via LinkedIn and thought-leadership campaigns.
  • Manage the entire sales cycle from prospecting through to deal closure.
  • Collaborate with the CEO and marketing on ideal customer profile, messaging, and sales collateral.
  • Establish early reference clients and champions for future expansion efforts.
  • Work with the product team to relay field feedback for ongoing improvement.
  • Monitor and analyze sales pipeline health, win rates, and deal velocity.

Benefits

  • Opportunities in a market valued at over $40B for AI-driven hiring solutions.
  • Access to unique technology including AI interview avatars and comprehensive ROI dashboards.
  • Potential for early equity stake and ownership as a founding team member.
  • Significant impact on building the U.S. revenue engine and shaping go-to-market strategies.
Full Job Description
Role Overview
This is one of JobTwine's first U.S. sales hire - a hands-on, founder-adjacent role for someone who can own the full sales cycle from prospecting to close. You'll target mid-market and upper-mid clients (500-5,000 employees) - tech-driven organizations that care deeply about talent quality, efficiency, and candidate experience. Your mission is to build a high exponentially growing sales engine in the next 12 months, build the early pipeline motion, and help shape our go-to-market strategy alongside the founder.

Requirements
• Hunt and close new logos in target verticals (Tech, IT Services, SaaS, Healthcare Staffing).
• Build a robust outbound and ABM motion via LinkedIn, warm intros, and thought-leadership campaigns.
• Own end-to-end deal cycle: prospecting → demo → business case → pilot → closure.
• Partner closely with the CEO and marketing to refine ICP, messaging, and collateral.
• Develop early reference clients and champions for expansion.
• Collaborate with the product team to provide feedback loops from the field.
• Track and report on pipeline health, win rates, and deal velocity metrics.

Ideal Profile
• 5-10 years of B2B SaaS sales experience, ideally selling AI, HRTech, or recruiting automation solutions.
• Proven success selling to Director+ or VP of TA, HR, or Business Unit Heads in mid-market companies.
• Comfortable running complex multi-stakeholder deals ($50K-500K ARR) with consultative discovery.
• Early-stage DNA - thrives in ambiguity, builds processes from scratch, and drives deals independently.
• Bonus: Experience at high growth HRTech startups in the US.
• Excellent written, verbal, and presentation skills - a storyteller who can sell vision + value.

Benefits

The estimated base salary range for this position is $110,000 - $125,000. Additionally this role includes quarterly commissions. The salary range provided is an estimate. Actual compensation may vary depending on the candidate's skills, qualifications, and experience

About Island Health

Island Health Careers

There has never been a better time to explore the job opportunities at Island Health, a leader in health care innovation and community wellness. Island Health stands out as a beacon of growth and professional development in the healthcare sector.

Work You’ll Do

Join Island Health’s dedicated team to assist in transforming healthcare delivery through cutting-edge innovation and exceptional leadership. Island Health offers a variety of positions that cater to the mastery of clinical practices and improvement of patient outcomes. Engage in a workplace where diversity training and leadership are at the core of daily operations, ensuring a culture that promotes inclusivity and respect across all levels of employment.

Island Health Job Opportunities

Island Health is building a robust employment system that supports both seasoned professionals and those at the beginning of their careers. Internship programs and entry-level positions provide a stepping stone for individuals aiming to excel in the healthcare industry.

Innovate and Lead

Island Health encourages its team to lead projects that harness innovative solutions to enhance patient care. This approach not only furthers personal career growth but also solidifies Island Health’s position at the forefront of healthcare innovation.

Be Part of a Great Team

Working at Island Health means being part of a team that values skills development and collaborative success. The company’s commitment to professional growth is evident through comprehensive benefits, continuous professional development, and opportunities for networking within the healthcare community.

Future-Proof Your Career

Island Health offers a pathway to a future-proof career through extensive training programs, certifications, and leadership development opportunities. The potential for advancement is vast, with support at each step to ensure every team member can achieve their career aspirations.

Explore Island Health’s Employment Culture

Island Health is recognized for its dynamic team environment and commitment to employee welfare. Prospective employees can look forward to joining a company that champions innovation and operational excellence.

The Island Health Hiring Process

Island Health’s hiring process is designed to be transparent and engaging, ensuring that all candidates are able to showcase their skills effectively. From the initial resume submission to the final interview, each step is an opportunity to demonstrate potential and fit within the Island Health culture.

Stay Connected with Island Health Careers

Join the Team

Search open positions that match your skills and interests. Island Health seeks passionate, curious, and solution-driven team players.

SEARCH ISLAND HEALTH JOBS

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Learn more about Island Health
Size
10,001 employees
Industry

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