Head of Enterprise Sales

Role Details

Location: Remote in the United States with a strong preference for San Francisco Bay Area.

This role is eligible for remote work.

Compensation: The annual OTE range for this role is $300,000 - $320,000 USD in addition to equity & benefits.

The range displayed on this job posting reflects the minimum and maximum target depending on the location of each candidate. In addition to location, other factors including level, job-related knowledge, skills, and experience will determine compensation.

About Gem

Gem is the AI-powered recruiting platform TA teams love. It helps you maximize productivity, hire faster, and save money – all while giving recruiters a solution they find easy to use. Use Gem as your all-in-one recruiting platform or enhance your existing ATS with integrated products for CRM, sourcing, scheduling, analytics, career sites, events, and more. Over 1,000 companies – from startups to industry leaders like Wayfair, Cintas, Carmax, DoorDash, and Zillow – trust Gem to hire with speed and ease. See why Gem is the recruiting industry’s most beloved solution, with a 4.8/5 rating on G2.

With Gem, You Can

• Attract, engage, and hire talent faster: Build talent pipelines across all channels through sourcing, nurture, events, career sites, inbound, and more. With Gem, teams can source talent five times faster and double their talent pipelines.
• Maximize recruiter productivity: Use AI and automation to save time on routine tasks like reviewing applications, scheduling interviews, and managing follow-ups. Recruiters using Gem can review twice as many applications, schedule twice as many interviews, and engage four times as many candidates as before.
• Unlock data-driven recruiting: Get analytics that everyone can use. Debug your funnel, monitor pipelines, forecast hiring, and demonstrate impact, all without complex BI tools. With Gem, TA teams use data to position themselves as strategic partners to the business.
• Simplify your tech stack and cut costs: Consolidate multiple tools into one platform and reduce your spend on recruiting technology, external sourcing, and job boards by up to 50%. Save on standalone solutions with Gem’s end-to-end bundle and take advantage of past candidate relationships to reduce your reliance on sourcing new talent.
  
  

And Just As We Strive To Help Our Customers Find Great Talent, We Also Invest In Our Own People And Culture. We Are Proud Of The Culture We’ve Built And Have Recently Been Recognized As

• Forbes America's Best Startup Employers 2024
• Great Place to Work Certified, 2023
• #13 on Fortune Great Places to Work, 2024!
  
  

The company has raised $148M in funding from Accel, Greylock, ICONIQ, and more.

The Team & Role

The Gem team is on a mission to improve the lives of talent acquisition professionals everywhere. We are passionate about helping leaders get the insights they need and allowing recruiters to automate the tedious parts of their work so they can spend time on what matters to them most.

Gem is experiencing incredible growth, and to accelerate even faster we are adding an experienced Head of Enterprise Sales to build and lead our team of high performing Enterprise Account Executives. We are seeking a leader who will inspire and lead our team, enabling them to continue to bring in new logos and grow them.

The Head of Enterprise Sales will be an expert in Enterprise Sales best practices. In this leadership role, the Head of Enterprise Sales will bring their own strong record of past success selling technology solutions in complex situations, along with a passion for ensuring the success and development of our team members. You will guide, motivate and problem solve to ensure your team is uncovering prospects’ and customers’ business pain in order to position Gem as a solution with a clear value proposition.

What You’ll Do Day-to-Day

• • Build and lead a high-performing Enterprise Sales team focused on net-new logo acquisition in Gem’s largest customer segment.
  • Own strategy and execution across pipeline generation, deal progression, forecast accuracy, and revenue performance.
  • Drive outbound excellence—develop high-quality opportunity creation through smart targeting, compelling messaging, and ABX programs.
  • Guide strategic deals—support reps with positioning, stakeholder engagement, and late-stage execution.
  • Set the tone on performance—create a high-standard, team-first culture built on accountability and strong coaching.
  • Act as a player-coach—jump in when needed to push deal strategy, coach live, and help reps level up.
  • Partner cross-functionally—collaborate with Marketing, Product, Solutions Consulting, Enablement, and CS to shape the GTM motion.
  • Instill operational rigor—drive consistency in forecasting, Salesforce hygiene, and process discipline.
  • Continuously improve how we sell—help raise the bar on sales execution, repeatability, and impact.
    

About You

• • 8–10+ years in B2B SaaS sales, including 3–5+ years leading Enterprise AE teams.
  • Consistent top performer with a track record of exceeding quota—as both an IC and a manager.
  • Strong outbound mindset—you know how to build pipeline and coach teams to generate demand; ABX experience is a plus.
  • Built in high-performing orgs, and ready for more ownership, impact, and a seat at the table.
  • Strategic and hands-on—you want to shape the playbook, not just run it.
  • Strong executive presence—confident with senior buyers and comfortable navigating complex deal cycles.
  • Fluent in value-based selling, with deep experience leading consultative, multi-threaded Enterprise deals.
  • Skilled in competitive displacement and consolidation—you’ve helped customers simplify their stack and drive platform value.
  • Energized by fast-paced environments—you move quickly, solve problems, and make things better.
  • Process-minded and organized—structured where it counts, flexible where it matters.
  • Collaborative by nature—you work well across functions and build strong internal partnerships.
    

Benefits

• Highly competitive salary & equity
• 10-year window to exercise your stock options
• Supportive Flexible Time Off program
• 16 paid holidays, including regular company-wide wellness days
• Best-in-class medical, dental & vision insurance
• $1,200 annual stipend for learning and development opportunities
• 16 weeks of Paid Parental Leave for birthing and non-birthing parents
• New Parent Perks totaling $1,500 and flexibility upon return to work
  
  

Gem is an equal opportunity employer. We celebrate our inclusive work environment and encourage folks of all backgrounds and perspectives to apply. At Gem, we’re committed to having an inclusive and transparent environment where every voice is heard and acknowledged. We embrace our differences, and know that our diverse team is a strength that drives our success.

Gem is committed to developing a barrier-free recruitment process and work environment. If you require any accommodation, please email us at accommodations@gem.com and we’ll work with you to meet your accessibility needs.

Gem’s Candidate Privacy Notice

By clicking “Submit Application”, you acknowledge and agree that you have read and understand Gem’s Candidate Privacy Statement, including the information provided on how Gem processes your personal data and your related rights as set forth therein.