Let’s get started
By clicking ‘Next’, I agree to the Terms of Service
and Privacy Policy
Jobs / Job page
Head of Square Enterprise Sales image - Rise Careers
Job details

Head of Square Enterprise Sales

At Square, we're transforming commerce by partnering with our largest and most strategic sellers to enhance their revenue channels. As we push upmarket in our next phase of growth, we're focused on delivering our comprehensive ecosystem to the largest sellers within our key audiences (Food and Beverage, Healthcare, Services, Events, and Payments) — ensuring they experience the full value and innovation Square has to offer.

We are seeking a leader with a proven track record in leading teams, selling, co-selling, and engaging with C-suite accounts, particularly within the Food and Beverage, Healthcare, Services, Events, and Payments sectors. You are entrepreneurial who drives a culture of excellence, consistently exceeding goals and targets. Your passion for developing and inspiring top-tier talent will unite employees, cross-functional teams, external partners, and customers around a shared vision of Square's potential in the upmarket space. You will report into our Head of Sales.

You Will:

  • Develop and implement a strategic vision for the Enterprise Sales Team, ensuring a consistent approach to delivering value for customers and partners.
  • Leverage data-driven insights to inform business strategies and refine our go-to-market approach.
  • Consistently meet and exceed revenue goals and key growth KPIs.
  • Expand and enhance the Enterprise seller experience.
  • Collaborate with the Sales Enablement team to establish effective learning and development plans for team members.
  • Foster a high-performance culture that embodies Square’s values of diversity, inclusion, and belonging.
  • Build and maintain strong cross-functional relationships to drive product innovation, marketing support, and new revenue opportunities.

You Have:

  • 10+ years of relevant experience, including 5+ years in management roles.
  • Proven track record of delivering revenue results in a company's largest segment while leading a team of experienced and technical sales professionals.
  • Experience managing geographically dispersed teams.
  • A strong track record of hiring and retaining top talent, developing leaders, and advancing their careers.
  • Comfort with ambiguity and experience in scaling fast-growing teams.
  • Expertise in introducing new products to market and evolving the sales narrative.
  • A passion for Square’s mission and values.
  • Experience with technical concepts, customers, and telling stories that balance vision setting with technical detail.
  • Professional and technical knowledge of industry trends and key players in the competitive landscape.
  • Demonstrated success in selling, co-selling, and breaking into C-suite accounts within the Food and Beverage, Healthcare, Services, Events, and Payments industries.

We're working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is a proud equal opportunity employer. We work hard to evaluate all employees and job applicants consistently, based solely on the core competencies required of the role at hand, and without regard to any legally protected class. We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we're doing to build an inclusive workplace? Check out our Inclusion & Diversity page

Full-time employee benefits include the following:

  • Healthcare coverage (Medical, Vision and Dental insurance)
  • Health Savings Account and Flexible Spending Account
  • Retirement Plans including company match
  • Employee Stock Purchase Program
  • Wellness programs, including access to mental health, 1:1 financial planners, and a monthly wellness allowance
  • Paid parental and caregiving leave
  • Paid time off (including 12 paid holidays)
  • Paid sick leave (1 hour per 26 hours worked (max 80 hours per calendar year to the extent legally permissible) for non-exempt employees and covered by our Flexible Time Off policy for exempt employees)
  • Learning and Development resources
  • Paid Life insurance, AD&D, and disability benefits

These benefits are further detailed in Block's policies. This role is also eligible to participate in Block's equity plan subject to the terms of the applicable plans and policies, and may be eligible for a sign-on bonus. Sales roles may be eligible to participate in a commission plan subject to the terms of the applicable plans and policies. Pay and benefits are subject to change at any time, consistent with the terms of any applicable compensation or benefit plans.

Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate's starting pay will be determined based on the candidate's work location and may be modified in the future.

Zone A - Zone D: USD $304,500.00 - USD $456,700.00

Amounts listed above include target variable compensation.

Block, Inc. (NYSE: SQ) is a global technology company with a focus on financial services. Made up of Square, Cash App, Spiral, TIDAL, and TBD, we build tools to help more people access the economy. Square helps sellers run and grow their businesses with its integrated ecosystem of commerce solutions, business software, and banking services. With Cash App, anyone can easily send, spend, or invest their money in stocks or Bitcoin. Spiral (formerly Square Crypto) builds and funds free, open-source Bitcoin projects. Artists use TIDAL to help them succeed as entrepreneurs and connect more deeply with fans. TBD is building an open developer platform to make it easier to access Bitcoin and other blockchain technologies without having to go through an institution.

Privacy Policy

Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering. Check out our other benefits at Block.

Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.

Privacy Policy

Block Glassdoor Company Review
4.1 Glassdoor star iconGlassdoor star iconGlassdoor star iconGlassdoor star icon Glassdoor star icon
Block DE&I Review
4.4 Glassdoor star iconGlassdoor star iconGlassdoor star iconGlassdoor star icon Glassdoor star icon
CEO of Block
Block CEO photo
Jack Dorsey
Approve of CEO

Average salary estimate

$380600 / YEARLY (est.)
min
max
$304500K
$456700K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

Similar Jobs
Photo of the Rise User
Block Remote Bay Area, CA, United States of America
Posted 10 days ago
Photo of the Rise User
Posted 3 days ago
Photo of the Rise User
Dental Insurance
Flexible Spending Account (FSA)
Health Savings Account (HSA)
Performance Bonus
Family Medical Leave
Paid Holidays
Photo of the Rise User
Posted 14 days ago
Photo of the Rise User
Datadog Hybrid New York, New York, USA; Denver, Colorado, USA; San Francisco, California, USA
Posted 3 days ago
Customer-Centric
Rapid Growth
Diversity of Opinions
Reward & Recognition
Friends Outside of Work
Inclusive & Diverse
Empathetic
Feedback Forward
Work/Life Harmony
Casual Dress Code
Startup Mindset
Collaboration over Competition
Fast-Paced
Growth & Learning
Open Door Policy
Rise from Within
Maternity Leave
Paternity Leave
Flex-Friendly
Family Coverage (Insurance)
Medical Insurance
Dental Insurance
Vision Insurance
Mental Health Resources
Life insurance
Disability Insurance
Health Savings Account (HSA)
Flexible Spending Account (FSA)
401K Matching
Paid Holidays
Paid Sick Days
Paid Time-Off
Photo of the Rise User
Posted 6 days ago
Posted 12 days ago
Photo of the Rise User
Posted 6 hours ago

Our purpose is economic empowerment.

140 jobs
MATCH
VIEW MATCH
BADGES
Badge Future MakerBadge InnovatorBadge Rapid Growth
FUNDING
SENIORITY LEVEL REQUIREMENT
TEAM SIZE
EMPLOYMENT TYPE
Full-time, on-site
DATE POSTED
February 18, 2025

Subscribe to Rise newsletter

Risa star 🔮 Hi, I'm Risa! Your AI
Career Copilot
Want to see a list of jobs tailored to
you, just ask me below!