Job Description

At Oversee, we are reimagining how corporate travel is managed.

Our advanced technology and machine learning eliminate outdated, manual processes that hold companies back - driving cost savings, improving efficiency, and enabling smarter decision-making.

We combine travel analytics with actionable insights, giving global enterprises the tools to gain visibility into their travel spend while continuously optimizing their programs.

We are the global leader for air and hotel reshopping solutions and also provide “AgentSee”, an AI-powered productivity tool designed to help Travel Management Companies (TMCs) work smarter and faster. AgentSee automates manual tasks like processing traveler emails, booking flights, and managing travel arrangements; enabling TMCs to reduce costs and improve service quality.

If you are looking for a dynamic, fast-paced, and positive environment and want to help solve a $17B global problem - Oversee is the place to build, grow, and make an impact.

We’re growing fast, with exponential YoY revenue growth and partnerships with some of the world’s largest Fortune 500 companies.

Why join us?

Sales enablement at Oversee isn't a maintenance role, it's a build role. T here is no inherited playbook, no legacy framework to patch, and no ceiling on the function's scope. You'll design the enablement architecture from scratch at a company selling technically complex AI and automation solutions into enterprise buying committees, at a moment when what we sell and how we sell it are both evolving fast.

This is a high-visibility, high-ownership seat with direct partnership across Sales, Product, and Marketing leadership and a direct line to the company's revenue trajectory.

Come shape the future of business travel with us!

What you'll do:

• Design and own Oversee's sales enablement strategy end-to-end, defining the frameworks, programs, and roadmap that scale with the business as we move upmarket and expand our solution portfolio;
• Build a repeatable onboarding and certification program for all customer-facing roles (AEs, SDRs, Solutions Engineers, Account Managers, and Sales Leaders), with clear milestones, assessments, and ramp benchmarks;
• Develop role-based learning paths and ongoing coaching programs that build capability progressively, not just at hire;
• Establish the company's enterprise sales methodology - operationalizing a consistent approach to discovery, qualification, value selling, multi-threading, and executive engagement across the entire revenue org;
• Create playbooks and training programs specifically for selling AI and agentic automation solutions, equipping teams to navigate both business and technical buying committees effectively;
• Define and document cross-functional engagement models across the sales cycle - clarifying how AEs, Solutions Engineers, SDRs, Customer Success, and Leadership collaborate from first touch through close and handoff;
• Establish best practices for technical demonstrations, proof-of-concepts, security reviews, and executive presentations, including handoff standards between sales, implementation, and customer success;
• Partner with Marketing to develop competitive positioning, battlecards, and sales content that reflect how buyers actually evaluate and select in our category;
• Work with Product and Engineering to ensure sales teams have current, accurate knowledge of our capabilities and roadmap so they can sell with confidence and credibility;
• Partner with Revenue Operations to identify skill gaps and productivity bottlenecks, and build a reporting framework around meaningful enablement metrics such as win rate, average sales cycle, AE ramp time, and others - to measure impact and continuously improve the program.

About you:

• 5+ years in Sales Enablement, Revenue Enablement, Sales Training, or a directly related leadership role, with a track record of building programs that move the needle on revenue metrics;
• Have built or significantly scaled an enablement function inside a high-growth B2B SaaS company - you know what a greenfield looks like and how to prioritize when everything feels urgent;
• Demonstrated success supporting enterprise sales organizations selling complex, technical solutions.You understand how enterprise deals actually move and what makes them stall;
• Experience enabling teams that sell platform, infrastructure, AI, automation, or workflow technology. You can translate technical capability into business value and teach others to do the same;
• Deep fluency in enterprise sales motions that involve both technical buyers (architects, IT, security) and business buyers (VP/C-suite). You've built programs that address both;
• Strong command of sales methodology, familiarity with MEDDPICC, Command of the Message, Challenger, or similar frameworks, and the judgment to know when to adapt rather than apply rigidly;
• Comfort working in a cross-functional, fast-moving environment. You can manage competing stakeholder priorities, build consensus, and ship programs without waiting for perfect conditions;
• Data-driven approach to program design: you measure what matters, iterate based on evidence, and can articulate the business impact of enablement investments to senior leadership;
• Experience supporting or closely partnering with Solutions Engineering / Sales Engineering teams is a strong plus.

Benefits are an important part of Oversee’s Total Rewards package, and this role is eligible for comprehensive coverage including medical, dental, vision, a 401(k) plan, paid time off, and more.

We are proud to be an equal opportunity workplace.

We provide employment opportunities without regard to race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or expression, or veteran status.