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Jack & Jill AI

VP Sales (+ Equity) at Cloud Capital

Sorry, this job was removed at 12:09 p.m. (CST) on Monday, Mar 30, 2026
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Hiring Remotely in United States
Remote or Hybrid
Hiring Remotely in United States

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The Director of Change Enablement leads initiatives to drive adoption of systems and process changes through strategic learning and stakeholder engagement.

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: VP Sales

Company Description: VC-backed cloud fintech SaaS

Job Description:

As the founding revenue leader, you will build a high-velocity mid-market sales engine from $1M to $25M+ ARR. You will act as a player-coach, personally mastering the sales motion before hiring and developing an academy-style team. This role owns the entire funnel, focusing on sharp discovery and rapid progression for CFO buyers.

Location: New York, USA

Why this role is remarkable:

  • Founding leadership opportunity to architect a go-to-market playbook from $1M ARR and capture a massive greenfield market.

  • Well-funded by top-tier VCs and led by a serial founder team with a proven track record of successful exits.

  • Rare chance to define a new category at the intersection of FinTech and cloud infrastructure with high-growth potential.

What you will do:

  • Master the sales motion as a player-coach by personally closing deals to refine the ICP and value proposition.

  • Build and lead a high-energy sales academy, hiring and coaching AEs through rigorous training and performance management.

  • Define and optimize the sales funnel, implementing signal-based stages and playbooks to increase velocity and predictability.

The ideal candidate:

  • Proven experience scaling B2B SaaS revenue from early stages to $10M+ ARR, ideally selling to the Office of the CFO.

  • Expert in mid-market, high-velocity motions with the ability to conduct technical demos and run 8-10 week cycles.

  • Exceptional coaching DNA with a track record of hiring, onboarding, and developing top-performing sales talent.

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.

Next steps

Step 1. Visit our website.

Step 2. Click 'Talk to Jack'.

Step 3. Talk to Jack so he can understand your experience and ambitions.

Step 4. Jack will make sure Jill (the AI agent working for the company) considers you for this role.

Step 5. If Jill thinks you're a great fit and her client wants to meet you, they will make the introduction.

Step 6. If not, Jack will find you excellent alternatives. All for free.

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.

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With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.

Key Facts About Chicago Tech

  • Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
  • Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
  • Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
  • Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
  • Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
  • Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory

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