Sales Enablement Manager

🕒 June 29

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Oversee (formerly FairFly)

WebsiteLinkedInAll Job Openings

11 - 50 employees

✈️ Travel

📦 Logistics

🤖 Artificial Intelligence

Travel • Logistics • Artificial Intelligence

Oversee is a company that specializes in travel spend optimization, providing comprehensive solutions for travel management companies, travel agencies, and online travel agencies. Its platform utilizes AI-driven tools to optimize travel policies, assure air and hotel prices, and transform fare and rate fluctuations into client savings. Oversee partners with businesses to ensure compliance, maximize travel budgets, and unlock growth opportunities without compromising service quality. Their technology aids in real-time sourcing optimization and contract auditing, ensuring significant discount savings and error reduction. The company is committed to elevating travel programs with data-driven insights and actionable supplier performance metrics, enhancing traveler experiences while maintaining cost-effectiveness.

📋 Description

• 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.

🎯 Requirements

• 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

• medical • dental • vision • a 401(k) plan • paid time off • more