Sales Director

Chegg Inc. • Trenton, NJ • 2h ago

Job DescriptionThe OpportunityChegg Skills is building the next chapter of Chegg. We operate at the intersection of workforce upskilling, career mobility, and outcomes-driven learning. While we benefit from Chegg's scale and credibility, we are intentionally distinct from "big Chegg" and its legacy.This role exists to build, scale, and lead the revenue engine that will define Chegg Skills' growth. We are looking for a Head of Sales who is more than a sales manager. This is a strategic, operational, and hands-on leader who can design systems, drive performance, coach teams, and close meaningful deals while navigating ambiguity.What You'll OwnRevenue Strategy & Growth Build and execute a clear sales strategy aligned to company growth goals Identify opportunities across markets, verticals, and channels Develop prospecting and closing strategies across:Direct B2BChannel partnersGovernmentHigher educationWorkforce and enterprise buyers Translate market insight into revenue actionSales Operations & Process Excellence Design and implement scalable sales processes, playbooks, and operating rhythms Own pipeline management, forecasting, and sales velocity metrics Build systems that drive consistency, clarity, and performance Establish clear performance standards and accountability frameworks Create processes that connect Sales with Product, Marketing, Operations, Engineering, and LeadershipTeam Leadership & Culture Build and lead a high-performing, low-ego sales organization Set the tone for culture, execution, and accountability Lead daily standups, pipeline reviews, and deal strategy sessions Facilitate deal swarms for high-value opportunities Step into deals when needed and coach in real time Develop talent through ongoing training, coaching, and performance managementStrategic Partnership Partner closely with the Head of Marketing to align demand generation and revenue execution Serve as a trusted consultant to leaders across the organization Translate business priorities into clear sales motions and outcomes Bring a revenue perspective to company-wide decisionsExecution in Ambiguity Operate effectively in an environment that combines startup speed with enterprise complexity Build structure where needed without slowing momentum Make smart decisions with imperfect information and adjust quickly Balance long-term strategy with immediate executionWho You AreYou are not just a sales leader. You are a builder and architect of revenue systems. Proven track record of building and scaling sales organizations Deeply data-driven and detail-oriented Experience designing sales processes, playbooks, and operating models from the ground up Comfortable in strategy conversations and live deals Understand GTM across multiple channels and buyer @types Skilled at coaching, training, and elevating sales talent Respected as both a leader and a partner Thrive in fast-moving, ambiguous environments Scrappy, resourceful, and execution-focusedWhat Great Looks Like in This Role A clear, repeatable, and scalable sales process exists across the organization The pipeline is healthy, predictable, and aligned to revenue goals Sales velocity, conversion, and deal quality improve consistently The sales team is coached, confident, and accountable Marketing and Sales operate as true partners Product and other teams have strong feedback loops from the market * Revenue becomes a function of system strength, not individual heroicsWhy This Role MattersThis is a defining role in building Chegg Skills' growth engine. You will not inherit a finished system. You will design it, build it, and scale it.If you are looking for comfort, this is not it.If you are looking for ownership, influence, and the chance to build something meaningful, this is.The On-Target Earnings (OTE) range for this position is $205,000 to $300,000, inclusive of any sales incentive, sales commission, or other form of variable comp

Similar Jobs

Coordinator Sales

Sage Hospitality Group • Philadelphia, PA • 1h ago

Sales & Marketing

Why us? American freedom gained its foothold in Philadelphia - a fiercely independent spirit that remained to infuse its commerce, its culture, and its people. At the intersection of it all - the very vibrant Logan Squar...

1h ago

Go to Apply

Outside Sales Representative

GLOBAL PAYMENT HOLDING COMPANY • Cherry Hill, NJ • 1h ago

Sales & Marketing

Every day, Global Payments makes it possible for millions of people to move money between buyers and sellers using our payments solutions for credit, debit, prepaid and merchant services. Our worldwide team helps over 3...

1h ago

Go to Apply

Sales Representative

Lithia & Driveway • New Jersey, New Jersey • 2h ago

Sales & Marketing

Dealership:L0701 DCH Brunswick Toyota DCH Brunswick Toyota Now Hiring: Sales Reps As an Auto Sales Representative you will interact and consult with customers to guide them through their vehicle purchase. Your goal is to...

2h ago

Go to Apply

Sales Rep - Admissions

Lincoln Technical Institute • Philadelphia, PA • 2h ago

Sales & Marketing

Admissions Sales Representative - Lincoln Tech Drive enrollment growth while changing lives through skilled trades education. Lincoln Tech is seeking a results-driven Admissions Sales Representative to identify, engage,...

2h ago

Go to Apply

Field Sales Executive, Cloud Software Solution Sales Remote

Wolters Kluwer • Trenton, NJ • 19h ago

Sales & Marketing

You may work from a remote home office location anywhere in or near AZ or NM The digital future has arrived and the tax and accounting professions are changing rapidly. Professionals today have different needs, expectati...

19h ago

Go to Apply

Field Sales Executive, Cloud Software Solution Sales Remote

Wolters Kluwer • Trenton, NJ • 19h ago

Sales & Marketing

19h ago

Go to Apply

Global Head, Inside Sales

Parexel • Trenton, NJ • 1d ago

Sales & Marketing

As Global Head, Inside Sales, you will shape the commercial engine of a world-class organization. This role is designed for a visionary commercial leader who thrives at the intersection of strategy, innovation, and execu...

1d ago

Go to Apply

Account Executive, Public Sector: State and Local Government

Salesforce • Philadelphia, PA • 2d ago

Sales & Marketing

Reference #: JR319909 To get the best candidate experience, please consider applying for a maximum of 3 roles within 12 months to ensure you are not duplicating efforts. Job CategorySales Job Details About Salesforce Sal...

2d ago

Go to Apply

2026 Canon Insights Summer Intern - Sales Support

Canon USA & Affiliates • Mount Laurel, NJ • 2d ago

Sales & Marketing

About the Role 2026 Canon Insights Summer Internship - Canon Financial Services (CFS) Canon Financial Services, Inc. is currently hiring for our 2026 Canon Insights Internship Program. The program will be held from Tuesd...

2d ago

Go to Apply

Marketing Director - Pharmaceuticals

Waters Technologies Corporation • Philadelphia, PA • 3d ago

Sales & Marketing

3d ago

Go to Apply

Subscribe to get new jobs sent directly to you
(no charge, cancel anytime)

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Similar Jobs

Coordinator Sales

Outside Sales Representative

Sales Representative

Sales Rep - Admissions

Field Sales Executive, Cloud Software Solution Sales *Remote*

Field Sales Executive, Cloud Software Solution Sales *Remote*

Global Head, Inside Sales

Account Executive, Public Sector: State and Local Government

2026 Canon Insights Summer Intern - Sales Support

Marketing Director - Pharmaceuticals

Field Sales Executive, Cloud Software Solution Sales Remote

Field Sales Executive, Cloud Software Solution Sales Remote