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 only AI-first all-in-one recruiting platform. It brings together your ATS, CRM, sourcing, scheduling, and analytics — plus 650+ million profiles to source from — with AI built into every workflow. By eliminating the headaches of juggling multiple tools, Gem helps customers boost recruiter productivity by up to 5x while saving 30-50% on technology costs. Over 1,000 organizations — from startups to industry leaders like Anthropic, Zillow, DoorDash, and Asana — trust Gem to fuel their growth. With an industry-leading 4.8/5 rating on G2, Gem is the platform recruiters actually love to use.

With Gem, You Can Experience The Power Of a Truly Connected Recruiting Platform — One Consistent Interface, Unified Data, Smarter AI Recommendations, And Simplified Permissions. Our Customers Achieve Remarkable Results

• Cut costs through consolidation: Replace your scattered recruiting tools with one AI-powered platform for ATS, CRM, sourcing, scheduling, and analytics. Reduce spend on expensive sources of talent and eliminate redundant point solutions.
• Maximize recruiter productivity: Get up to 5x efficiency gains with AI built into every workflow — from sourcing talent and reviewing applications to scheduling interviews and managing candidates. With all products working better together, recruiters spend less time switching systems and more time building relationships.
• Unlock data-driven recruiting: Get access to analytics across the recruiting funnel without complex BI tools. From pipeline metrics to hiring forecasts, Gem helps you make data-driven decisions and demonstrate impact.
• Use AI that actually works: Get better results from AI that learns from all your recruiting data. With insight into every candidate touchpoint and interaction, Gem AI makes smarter decisions about who to engage and how.
• Work with software built for recruiters: Use a platform designed around how recruiters actually work, not a collection of technical features. Quick implementation, intuitive workflows, and clear analytics make Gem the solution teams actually use and trust, earning us an industry-leading 4.8/5 rating on G2.
  
  

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, 2024 - And we landed at number #13!
• Fortune Best Workplaces for Millennials, 2023
  
  

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.

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