Director, Enterprise Sales

About Juicebox

Juicebox is on a mission to help teams win the talent war.

In the age of AI, human ingenuity is the ultimate scarce resource. Recruiting is a zero-sum game where you either compete or lose.

Teams at Ramp, Notion, and leading AI labs use Juicebox to power their hiring, alongside 5,000+ customers from early-stage startups to Fortune 500 companies.

We are on the path to $100M in ARR with 20%+ monthly growth, powering thousands of searches every day and making Juicebox one of the fastest-growing AI SaaS companies in the world.

Juicebox has raised over $116M in funding from lead investors including Sequoia Capital, DST Global, and NFDG. Read more about our $80M Series B https://juicebox.ai/blog/series-b here. Additional investors in Juicebox include Y Combinator, Coatue, Bond, Lux, Verified Capital, and Committed Capital.

ABOUT THE ROLE

A career-defining opportunity to be a founding member of the Sales Leadership team, reporting directly to the VP of Sales.

This role will be responsible for overseeing and developing our growing Enterprise Account Executive team to drive new logo growth. You’ll own the strategy and execution behind our most complex and strategic opportunities, helping the team navigate sophisticated buying committees, executive stakeholders, and multi-threaded enterprise sales cycles.

You’ll partner closely with GTM cross-functional peers, as well as the founders, to help scale Juicebox into its next chapter. You’ll also play a critical role in shaping our enterprise GTM motion, from defining how we segment and penetrate strategic accounts to developing the playbooks that allow us to consistently win larger, more complex deals.

This is a both a tactical and strategic role. You’ll work directly with reps on pipeline management, deal execution, forecasting, coaching, customer meetings, and sales strategy, while also helping architect how our broader sales organization scales over time.

We’re looking for builders who are motivated to elevate the GTM craft within one of the fastest-growing AI companies. You’ll shape culture, get runway to implement new ideas, and have fun doing it.

YOU WILL

- Lead and Develop: Lead and develop a team of Enterprise Account Executives in our San Francisco headquarters.

- Own Your Business: Own pipeline generation, forecasting, deal execution, and team performance.

- Win Complex Deals: Coach and actively participate in high-stakes enterprise opportunities, helping reps navigate multi-threaded buying committees, executive stakeholders, procurement, security, legal, and complex commercial negotiations.

- Build Executive Relationships: Establish credibility with senior customer stakeholders and step directly into strategic opportunities when leadership involvement can accelerate or unlock a deal.

- Drive Enterprise Account Strategy: Develop rigorous account planning, territory strategy, pipeline creation, and whitespace identification across our highest-value prospects.

- Set the Pace: Create a rhythm on your team complete with 1:1s, team meetings, deal reviews, coaching and development, and more.

- Raise the Enterprise Sales Bar: Develop AEs into strategic, consultative sellers capable of leading sophisticated discovery, building compelling business cases, quantifying value, and selling to executive audiences.

- Build the Business: Establish playbooks, sales motions, and systems/processes alongside key peers in Revenue Operations, Customer Success, Sales Development, Marketing, and more.

- Shape the Enterprise Motion: Partner with Product, Marketing, Customer Success, and leadership to translate learnings from strategic customers into improvements across positioning, packaging, product strategy, and our broader enterprise GTM motion.

- Get Creative: We’re always looking for fresh perspectives to scale our business effectively, and fast!

YOU HAVE

- 7+ years of experience in B2B SaaS sales environments, including 3+ years leading Enterprise sales teams.

- A track record of leading teams that consistently close complex, high-value enterprise software deals.

- Deep experience coaching enterprise sellers across account strategy, executive discovery, multi-threading, business-case development, negotiation, and closing.

- Experience building predictable enterprise pipeline and forecasting accurately across longer, less linear sales cycles.

- Strong executive presence and comfort engaging directly with VP- and C-level buyers.

- Experience scaling within early-stage or high-growth startup environments.

- Low ego: we have too much to do with too little time.

- Intellectually curious; you chase big questions and come up with unique solutions.

- High-performance and people-oriented.

- Comfortable operating in ambiguity and fast-moving environments.

- AI fluent with enthusiasm for modern GTM tooling.

- A strong communicator who can motivate and develop high-performing teams.

BONUS POINTS IF...

- Experience helping scale a company from Series B through later growth stages.

- Background at companies known for strong product-led or modern GTM cultures.

- Strong opinions around sales tooling, systems, and GTM infrastructure.

- Experience building or materially evolving an enterprise sales motion as a company moved upmarket.

- Experience selling into large, complex organizations where security, procurement, legal, and multiple business stakeholders are central to the buying process.

Perks & Benefits for all Full Time Employees

- Top-of-market compensation with meaningful equity, because everyone should share in our success.

- Daily meals provided: breakfast catering, lunch order via DoorDash corporate, and for those who like to work late, dinner if staying after 7pm

For US Employees:

- Comprehensive healthcare with 100% employer-paid medical coverage for employees (PPO Platinum plan with $0 deductible). 90% employer contribution for dependents. Dental & Vision: 90% employer covered; 85% for dependents.

- $2,000 annual wellness stipend to support your physical, mental, and financial well-being.

- $300/month commuting stipend to help cover the cost of getting to and from the office.

For UK Employees:

- Comprehensive private medical insurance with £0 excess, full outpatient cover, comprehensive cancer care, mental health treatment, and 24/7 GP access.

- £1,500 annual wellness stipend to support your physical, mental, and financial well-being

- £3,500/year commuting stipend to help cover the cost of getting to and from the office.