Director OF Training, SALES Technology (remote - nc) - Remote Eligible

Job Summary:

Compass Group is seeking an experienced and strategic Director of Sales Training and Coaching to lead the development and execution of full-cycle sales enablement across our national sales organization. This leader will serve as a key connector across sales stages, providing hands-on support to sellers and sales leaders through real-time deal reviews, coaching, After-Action Reviews (AARs), Fishbone analysis, and structured foundational training. Our goal is not just to facilitate in-room training to equip, but also to adopt peer-to-peer and on-the-job training so it is truly adopted.

As Compass evolves its go-to-market approach, this role will play a central part in reinforcing our sales process, supporting live opportunities, and building the muscle for repeatable success. The ideal candidate has walked in the shoes of sellers and sales managers, understands the pace and complexity of the sales environment, and brings a passion for coaching, enablement, and execution.

Responsibilities:

Lead and deliver immersive full-cycle sales training that embeds Compass Group's sales methodology into every stage of the process, from discovery through proposal, pricing, negotiation, and close.

Reinforce the sales process not just in the classroom, but across live opportunities, peer-to-peer learning, on-the-job coaching, and manager-led development.

Collaborate closely with sellers, sales leaders, and all functions of Sales Support to identify performance gaps and create practical, high-impact training and coaching solutions.

Facilitate real-time deal reviews, After-Action Reviews, Fishbone sessions, and strategy discussions with cross-functional stakeholders to uncover insights, replicate wins, and improve execution.

Deliver training using multiple formats, including in-person facilitation, virtual workshops, on-the-job development, and structured peer learning.

Design and scale blended learning experiences that include role-specific training, micro-learning, and modular sessions to meet diverse learning needs and drive retention.

Build repeatable systems, playbooks, and self-serve resources that help sellers adopt and sustain best-in-class behaviors at every stage of the sales funnel.

Partner with Sales Operations, Sales Finance, Enablement, and Proposals to align training with tools, business objectives, and key initiatives.

Define and track clear performance metrics using data and feedback loops to assess coaching impact and evolve training content.

Act as a trusted advisor to frontline managers and RSDs, equipping them with coaching frameworks, tools, and ongoing reinforcement strategies not just in the classroom but in day to day and peer to peer.

Qualifications:

8 or more years of experience in sales, sales leadership, or sales coaching roles with a strong focus on enterprise or consultative selling.

Serve as a self-starter with a relentless focus on getting 1% better every day, helping to drive a culture of learning, reflection, and continuous improvement.

Firsthand experience as a seller and sales manager, with a deep understanding of the challenges and rhythms of the sales environment.

Proven ability to lead deal reviews, AARs, and strategy sessions that result in measurable improvement in seller performance.

Skilled facilitator in both classroom and virtual environments, with the ability to adjust content and delivery based on audience needs.

Strong understanding of sales process design, coaching strategy, and how to apply both in the field.

Ability to work cross-functionally and influence across departments to support key sales initiatives.

Fluent in coaching for behavior, execution, and mindset, not just knowledge transfer.

Committed to building a culture of continuous learning, honest reflection, and consistent performance.

Compass Group is an equal opportunity employer. At Compass, we are committed to treating all Applicants and Associates fairly based on their abilities, achievements, and experience without regard to race, national origin, sex, age, disability, veteran status, sexual orientation, gender identity, or any other classification protected by law.

Qualified candidates must be able to perform the essential functions of this position satisfactorily with or without a reasonable accommodation.

Compass Corporate maintains a drug-free workplace.

Applications are accepted on an ongoing basis.

Associates at Corporate are offered many fantastic benefits.

Medical

Dental

Vision

Life Insurance/ AD

Disability Insurance

Retirement Plan

Paid Time Off

Paid Parental Leave

Holiday Time Off (varies by site/state)

Personal Leave

Associate Shopping Program

Health and Wellness Programs

Discount Marketplace

Identity Theft Protection

Pet Insurance

Commuter Benefits

Employee Assistance Program

Flexible Spending Accounts (FSAs)

Associates may also be eligible for paid and/or unpaid time off benefits in accordance with applicable federal, state, and local laws. For positions in Washington State, Maryland, or to be performed Remotely, click here for paid time off benefits information.