Meet Jack and Jill. Two AI agents that introduce remarkable people to remarkable companies. Jack is an AI agent that finds your next job and helps you land it. Already helping over 230,000 people take the next step in their career. Jill is an AI agent for recruiting. Already helping thousands of companies make their next great hire. 

Here's where it gets interesting. Jack and Jill work together. Jack knows what professionals are looking for, long before they're ready to move. Jill knows what thousands of companies need, far beyond what's written in the job description. When both sides match, they introduce the candidate and the decision maker directly. 

No cold outreach. No black hole. Just warm introductions that work.

Jack

AI Agent

Jill

Jack & Jill

Meet Jack and Jill. Two AI agents that introduce remarkable people to remarkable companies.

This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers.

She will pick the best candidates from Jack's network.

The next step is to speak to Jack.

Job Title

Builder Account Executive, Enterprise Healthcare Sales

Salary

$180k-$250k OTE

Company Description

Springboard.com is a $31M Series B edtech leader based in San Francisco, revolutionizing how health systems solve the workforce crisis. They design and deliver certified, mentor-led training programs that turn employers into "talent makers," partnering with major IDNs to build sustainable pipelines for critical allied health roles across the United States.

Job Description

Join Springboard.com to lead complex, consultative sales cycles targeting the healthcare C-suite. You will own the full enterprise lifecycle, architecting tailored workforce solutions that solve urgent clinical gaps for major health systems. This is a high-impact "builder" role for a relentless closer ready to solve a mission-critical crisis rather than just sell software.

Location

Remote, USA

Why this role is remarkable

Own a mission-critical solution: You are selling a remedy to the national healthcare workforce crisis, shifting hospitals from "talent takers" to "talent makers" with a high-ROI model.Strategic Series B Growth: Backed by $31M in funding, you’ll join a high-traction edtech leader during a pivotal expansion of their Springboard Health B2B unit.High-Stakes Autonomy: This isn't a "product-in-a-box" role; you have the creative freedom to architect custom solutions and influence product strategy based on C-suite feedback.

What You Will Do

Drive the full enterprise sales lifecycle from cold prospecting to closing multi-stakeholder deals with COOs, CHROs, and CEOs at the IDN level.Architect bespoke workforce development solutions by collaborating with Learning Design and Leadership teams to address specific clinical and operational gaps.Iterate the sales playbook in real-time, diagnosing business case failures and adjusting positioning to navigate 6–18 month bureaucratic healthcare sales cycles.

The ideal candidate

7+ years of experience in Enterprise Sales, specifically closing high-ACV complex services or consultative solutions within large health systems.Proven ability to build compelling business cases for CFOs and Chief People Officers, translating training outcomes into clear financial and operational ROI.Exceptional resilience and stamina, with a track record of navigating long sales cycles and creating structure in high-growth, ambiguous environments.

Who are Jack & Jill?

Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.

And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.

How does this work?

Jack's an AI agent for job searching and career coaching. He works for you.Jill is the AI recruiter working for the company. She recruits from Jack's network.If it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives.

We never post fake jobs

This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.

Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.

We appreciate this can make them look a bit suspect, but there isn't much we can do about it.

Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.



Builder Account Executive, Enterprise Healthcare Sales ($180k-$250k OTE) at Springboard

What the job involves