Jack & Jill
Sales Enablement Leader at Oversee
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Job Title
Sales Enablement Leader
Salary
Not Disclosed
Company Description
Oversee is a high-growth travel tech leader reimagining corporate travel through AI and machine learning. Serving over half the Fortune 500 and solving a $17B global problem, Oversee automates manual processes for global enterprises and Travel Management Companies with its industry-leading reshopping and productivity tools.
Job Description
Join Oversee as a hands-on leader to build our sales enablement function from the ground up. You will design the end-to-end architecture for selling complex AI and automation solutions to enterprise buying committees. Partnering with Sales, Product, and Marketing, you will directly influence our revenue trajectory during a period of exponential growth.
Location
UK or Europe
Why this role is remarkable
- This is a pure build role with no legacy frameworks or inherited playbooks, offering a complete greenfield to design the company's global enablement architecture from scratch.
- Work at the forefront of the $17B travel management market with a company that already partners with over half the Fortune 500 and is seeing exponential YoY growth.
- You will be a high-visibility strategic partner to Sales, Product, and Marketing leadership, directly shaping how the company sells technically complex, agentic AI solutions to sophisticated enterprise buyers.
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What You Will Do
- Design and own the end-to-end sales enablement strategy, including the frameworks, onboarding programs, and certification roadmaps that scale as the business moves upmarket.
- Operationalize a consistent enterprise sales methodology, such as MEDDPICC or Command of the Message, across discovery, qualification, multi-threading, and executive engagement cycles.
- Create playbooks and training specifically for agentic AI solutions, equipping customer-facing teams to navigate both technical (IT/Security) and business (C-suite) buying committees effectively.
The ideal candidate
- You have 5+ years of experience in Sales or Revenue Enablement and a proven track record of building an enablement function from zero within a high-growth B2B SaaS company.
- You possess deep expertise in enterprise sales motions for complex, technical products like AI, automation, or infrastructure, with the ability to translate technical features into business value.
- You are a data-driven, hands-on doer who can author content and run training sessions while building reporting frameworks to measure impact on win rates and ramp times.
Who are Jack & Jill?
- Jack: I'm 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.
- Jill: I'm 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.
Get help with your application
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How does this work?
- Jack: An AI agent for job searching and career coaching. He works for you.
- Jill: 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.
“It took my CV and asked me questions relevant to understanding what kind of jobs to suggest for me. Suggestions were almost perfect. Jobs were exactly what I’ve been looking for.”
Jessica, London
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