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Square

Head of Revenue Operations and Enablement

Sorry, this job was removed at 06:29 p.m. (EST) on Tuesday, Feb 04, 2025
Remote
Hybrid
8 Locations
Remote
Hybrid
8 Locations

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn't work together.
So we expanded into software and started building integrated, omnichannel solutions - to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we've embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.
Today, we are a partner to sellers of all sizes - large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We're building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.
The Role
The Block Sales team is looking for a Head of Revenue Operations & Sales Enablement leader. This role is responsible for helping our global Sales and Account Management teams to serve our diverse customer base by optimizing revenue generation and operational efficiency. This leader will be responsible for developing and executing a comprehensive revenue operations strategy that supports our business objectives and accelerates growth. The ideal candidate is a strategic thinker with a proven track record in leading large initiatives at scale, partnering with cross-functional teams, and making work more effective and efficient for sales reps and account managers.
You Will

  • Evangelize the function by determining and communicating success metrics for our all revenue generating and support roles
  • Lead all elements of the strategic planning process for Block sales
  • Assume direct responsibility for the project management of all major initiatives that span across our Revenue and Enablement function
  • Ensure the revenue organization has the right support and infrastructure to beat its annual plan objectives
  • Lead a variety of functions spanning technical program management, instructional design, enablement, sales compensation, and CRM
  • Work cross functionally with commercial, product, finance, marketing, growth, and engineering leaders across Block to ensure the revenue team's plans are being supported by our partner organizations, and that all new launches and projects are aligned across functions


You Have

  • 12+ years of experience in revenue operations, sales operations and enablement, ideally in a fast-paced and high volume sales motion.
  • Proven track record of successfully leading and scaling revenue operations functions.
  • Strong analytical skills with the ability to interpret complex data and provide actionable insights. You can turn ambiguity into clarity, and turn complexity into simplicity.
  • Excellent leadership and team management skills, with experience leading cross-functional teams.
  • Proficiency in CRM software (e.g., Salesforce), automation tools, and data analytics platforms.
  • Exceptional communication and interpersonal skills, with the ability to influence stakeholders at all levels.
  • A deep understanding of curriculum and instructional design for Sales organizations.
  • Demonstrated success when leading a multidisciplinary organization of L&D workstreams (and managing professionals across these disciplines).
  • A history collaborative approach to incorporate Product & Marketing knowledge into the enablement journey.
  • A solution-oriented mindset, unmatched resilience and resourcefulness, and the ability to learn new things at a rapid pace.


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 an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We also consider qualified applicants with criminal histories for employment on our team, and always assess candidates on an individualized basis.
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 a workplace that is fair and square? Check out our I+D page .
Block will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and "fair chance" ordinances.
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 job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.
To find a location's zone designation, please refer to this resource . If a location of interest is not listed, please speak with a recruiter for additional information.
Zone A:
$217,800 - $326,800 USD
Zone B:
$217,800 - $326,800 USD
Zone C:
$217,800 - $326,800 USD
Zone D:
$217,800 - $326,800 USD
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, healthcare coverage, flexible time off, and modern family planning are just some of our offerings. 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.

Square Toronto, Ontario, CAN Office

Toronto, Ontario, Canada

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