Head of Sales at AI-driven enterprise benefits platform

Jack & Jill/External ATS
London

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 Jacks network.

The next step is to speak to Jack.


Head of Sales

Company Description: AI-driven enterprise benefits platform

Job Description:
As Head of Sales you will lead the go-to-market strategy for an innovative HR technology platform. You will be responsible for scaling a high-performing sales team while maintaining a hands-on approach to closing mid-market enterprise deals. This role is pivotal in establishing the first AI-powered operating system for global employee management.

Location: London UK

Why this role is remarkable:

  • Lead the sales function for a disruptive platform building the worlds first AI-powered OS for employee benefits.

  • Join a well-funded startup backed by top-tier VCs at a critical phase of global expansion and growth.

  • Enjoy a high-impact hands-on leadership role with significant room to scale your career alongside the growing team.

What you will do:

  • Manage and scale the go-to-market team to consistently hit aggressive revenue and growth targets.

  • Take a hands-on approach to the sales cycle deeply involving yourself in client processes and enterprise negotiations.

  • Implement AI-driven strategies to optimize sales efficiency and maintain a competitive edge in the HR tech market.

The ideal candidate:

  • Proven track record of success in enterprise sales specifically selling complex software to mid-market and large organizations.

  • Deep understanding of AI and its transformative impact on SaaS with the ability to articulate this value to stakeholders.

  • Willingness to be both a strategic leader and a hands-on contributor who gets into the trenches with the team.

Who are Jack & Jill
Ok Ill go first. Im Jack an AI that gets to know you on a quick call learning what youre 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 Im Jill an AI Recruiter who talks to companies to understand who theyre looking to hire. Then I recruit from Jacks 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 youre 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 isnt a trick. This is an open role that Jill is currently recruiting for from Jacks network.
Sometimes Jills clients ask her to anonymize their jobs when she advertises them which means she cant share all the details in the job description.
We appreciate this can make them look a bit suspect but there isnt 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 were giving his services away for free.

Required Experience:

Director

Posted 2026-01-03

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